- Synthesis of a novel methylene-bridged biscarbazole derivative and evaluation of its DNA and nucleotide binding properties
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The synthesis of a novel methylene-bridged biscarbazole derivative 1 was described and the possible mechanism for its unexpectedly synthesized intermediate, compound A, was postulated. The binding properties of 1 to both Ct-DNA and nucleotides were investigated via fluorescent and UV-Vis spectra. The spectral investigations illustrated that this binary carbazole exhibited higher binding abilities to both Ct-DNA and nucleotides than its monomeric form, owing to the structurally flexible nature of double carbazole moieties fine-tuned by this non rigid methylene-linkage.
- Li, Gang,Zhou, Xue,Yang, Peng,Jian, Yong,Deng, Tuo,Shen, Hongyan,Bao, Ying
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- Synthesis and photovoltaic properties of functional dendritic oligothiophenes
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Novel p-type and low bandgap functional dendritic oligothiophenes bearing hole-transporting carbazole as peripheral substituents and an electron-withdrawing dicyanovinyl core group, namely, DCT(n)-DCN, where n = 1 or 2 for solution-processable photovoltaic (PV) applications have been synthesized. With electron-donating carbazole surface-functionalized moieties conjugated with dicyanovinyl core group, the optical bandgap of these functional dendritic oligothiophene thin-films greatly reduces to 1.74 eV with a strong spectral broadening and a high ionization potential at ～5.5 eV as determined by UV photoelectron spectroscopy. The bulk heterojunction PV cells fabricated from these dendrimers blended with PC71BM as an acceptor showed a power conversion efficiency up to 1.64% with an open circuit voltage of (V oc) = 0.93 V in the annealed device. We have demonstrated that the desirable molecular and PV properties of dendritic oligothiophenes can be obtained/tuned by the incorporation of functional group(s) onto peripheral of the dendron and into the core. In addition, these functional dendritic oligothiophenes show superior functional properties even at low dendritic generation as compared to the unsubstituted higher generation dendritic oligothiophenes as a p-type, low-bandgap semiconductor for solution-processable bulk heterojunction PV cells.
- Zhang, Weifeng,Ng, Ging Meng,Tam, Hoi Lam,Wong, Man Shing,Zhu, Furong
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- A highly reactive (<1 min) ratiometric chemodosimeter for selective "naked eye" and fluorogenic detection of hydrazine
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Hydrazine is an important industrial chemical but also very toxic. Thus rapid detection of hydrazine is very important. We have judiciously designed and constructed a novel ICT-based ratiometric "naked eye" and fluorescence smart probe, carbazole based malononitrile (CBM), that rapidly (1 min) and selectively detects hydrazine in the presence of different metal ions, anions and other amines in aqueous medium. As a possible application of the probe, hydrazine sensing in tap water was tested. The probe also shows an excellent performance in the "dip stick" method. The Royal Society of Chemistry 2013.
- Goswami, Shyamaprosad,Paul, Sima,Manna, Abhishek
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- A fast-responsed fluorescent probe for the selective detection hydrogen sulfide and tert- butoxy radical
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The fluorescent probe (1) for detecting hydrogen sulfide and tert-butoxy radical in aqueous environment and living cells was first developed. The probe 1 displayed excellent optical properties such as good selectivity, low detection limit (21 nM), quantitative detection (1–10 μM), and very fast response times (50 s) for monitor of hydrogen sulfide in aqueous environment. Furthermore, the color of the probe 1 solution changed from yellow to colorless when hydrogen sulfide added. More importantly, the probe 1 is successfully used to real-time imaging for hydrogen sulfide and tert-butoxy radical in Hela cells. These merits play a significant role in the process for hydrogen sulfide detection considering the rapid metabolism in organisms.
- Dong, Junyang,Hu, Jianfeng,Zhang, Hao
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- Synthesis of novel viscosity sensitive pyrrolo-quinaldine based styryl dyes: Photophysical properties, electrochemical and DFT study
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We have synthesized two novel styryl dyes namely (E)-2-(2-(9-butyl-9H-carbazol-3-yl)vinyl)-3,3,8-trimethyl-3H-pyrrolo[3,2-h]quinoline (PQC) and (E)-10-butyl-3-(2-(3,3,8-trimethyl-3H-pyrrolo[3,2-h]quinolin-2-yl)vinyl)-10H-phenothiazine (PQPT). These dyes were characterized by FT-IR, HR-MS, 1H and 13C NMR spectroscopy techniques. Both dyes displayed absorption wavelength within the range of 399?427 nm. Ranging from non-polar solvents towards polar solvents, these dyes exhibited emission wavelength and Stokes shift from 487?605 nm and 85?180 nm respectively. The photophysical study of these dyes in seven solvents suggested that these dyes show positive emission solvatochromism which was investigated from Reichardt's ET (30) plot, Lippert-Mattaga graph and MacRae solvent polarity scale plots. In addition, these dyes show evidence of intramolecular charge transfer properties which were explained with the assist of Wellers, Rettig plots and ground-excited states dipole moment difference. The electrochemical properties of these dyes were investigated with the help of cyclic voltammetry and differential pulse voltammetry. Viscosity sensitivity studies were also performed on the synthesised dyes in the methanol and polyethylene glycol 400 system with varying viscosity of the solvent system. The thermal properties of these dyes were investigated using TGA and DSC analysis, which shows that dyes were thermally stable up to 200 °C. The theoretical photophysical properties of these dye molecules was explored by density functional theory (DFT) along with the time dependent density functional theory (TD-DFT).
- Chaturvedi, Ankur,Jachak, Mahesh,Joglekar, Amruta,Khopkar, Sushil,Shankarling, Ganapati
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- Highly reactive (<1 min) ratiometric "naked eye" detection of hypochlorite with real application in tap water
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The de-diaminomaleonitrile reaction in a simple carbazole diaminomaleonitrile hybrid (CDH) was promoted by OCl- which disrupted the ICT mechanism by breaking the donor and acceptor linkage. This system utilized an irreversible OCl- promoted oxidation reaction and it responded instantaneously at room temperature. The chemosensor also showed excellent performance in tap water and the "dip-stick" method.
- Goswami, Shyamaprosad,Paul, Sima,Manna, Abhishek
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- Preferential intermolecular interactions lead to chiral recognition: Enantioselective gel formation and collapse
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Interesting self-assembly of an amino acid based molecular material into a hydrogel in the presence of selective enantiomeric chiral amines leading to chiral recognition has been demonstrated. Moreover, collapse of a metallogel formed from the same material in the presence of selective enantiomers validated its enantioselective affinity. Importantly, in addition to relevant experimental techniques, DFT studies have been successfully explored to establish chiral recognition through enantioselective gelation.
- Gambhir, Diksha,Kumar, Sunil,Dey, Gourab,Krishnan, Venkata,Koner, Rik Rani
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- Carbazole-benzimidazole based dyes for acid responsive ratiometric emissive switches
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Three carbazole based benzimidazole derivatives exhibiting the effect of intramolecular charge transfer (ICT) caused by the donor-acceptor interaction between their carbazole and benzimidazole units were synthesized. Their photophysical properties were systematically investigated in various solvents with different polarities. Positive solvatofluorochromic effects were observed with the change of solvent from non-polar to polar for all of the three dyes. The synthesized compounds presented proton-induced absorption as well as ratiometric emission changes, indicating that these compounds might be used as proton sensors. The dyes in their solid state are also able to detect acid vapours. The optimized structures of the dyes and their protonated forms were calculated by density functional theory calculations.
- Aich, Krishnendu,Das, Sangita,Goswami, Shyamaprosad,Quah, Ching Kheng,Sarkar, Deblina,Mondal, Tapan Kumar,Fun, Hoong-Kun
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- A large dipole moment to promote gelation for 4-nitrophenylacrylonitrile derivatives with gelation-induced emission enhancement properties
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A series of 4-nitrophenylacrylonitrile and phenylacrylonitrile derivatives consisting of a carbazole moiety was synthesized. Some of these derivatives with longer alkyl chains and a nitro group could gelatinize some organic solvents, such as ethanol, n-butanol, ethyl acetate, and DMSO. By contrast, phenylacrylonitrile derivatives did not form gels in measured solvents. This result proved that the electron-withdrawing nitro moiety was important for gel formation because it conferred the molecules with large dipole moments, which enhanced the intermolecular interaction. Analyses by UV-vis absorption, X-ray diffraction, and scanning electron microscopy showed that the gelator molecules could self-assemble into one-dimensional nanofibers with layer packing, which further twisted into thicker fibers and formed three-dimensional networks in the gel phase. The single crystal structure of C4CNPA implied that the gelators might adopt an anti-parallel molecular stacking because of their larger ground-state dipole moment. Interestingly, the organogels had enhanced fluorescence relative to solutions at the same concentrations. This journal is the Partner Organisations 2014.
- Xue, Pengchong,Yao, Boqi,Zhang, Yuan,Chen, Peng,Li, Kechang,Liu, Baijun,Lu, Ran
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- Synthesis and optical properties of some compounds based on carbazole and s-triazine
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A hyperbranched conjugated polymer (P), as well as its repeating units (M), have been synthesized based on 2,4,6- trimethyl-s-triazine and formylcarbazole. Compared with M, P exhibits much stronger fluorescence and a larger SternVolmer constant (KSV) in response to DNT, indicating a fluorescence signal amplification effect in the hyperbranched conjugated polymer P.
- Diao, Lixiao,Cui, Yuezhi,Li, Tianduo,Zhou, Longlong,Liu, Wenxia
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- Synthesis and Characterization of Carbazole-Based Dendrimers with Porphyrin Cores
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A series of novel dendritic carbazole-based porphyrins [T(Cz-Gn)Ps] have been synthesized by a combination of Ullmann coupling and Adler condensation reactions and their intramolecular energy-transfer properties have been studied by absorption and steady-state fluorescence spectroscopy. It has been found that the light-harvesting capabilities of T(Cz-Gn)Ps increase with increasing generation, but that the efficiency of the enrgy transfer decreases from T(Cz-G0)P to T(Cz-G2)P due to the Foerster energy-transfer process. In addition, these dendritic macromolecules can emit intense red light with high fluorescence quantum yields and so may find applications in photonic devices.
- Xu, Ting Hua,Lu, Ran,Qiu, Xian Ping,Liu, Xing Liang,Xue, Peng Chong,Tan, Chang Hui,Bao, Chun Yan,Zhao, Ying Ying
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- Long-Lived Triplet Excited State Accessed with Spin–Orbit Charge Transfer Intersystem Crossing in Red Light-Absorbing Phenoxazine-Styryl BODIPY Electron Donor/Acceptor Dyads
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Orthogonal phenoxazine-styryl BODIPY compact electron donor/acceptor dyads were prepared as heavy atom-free triplet photosensitizers (PSs) with strong red light absorption (?=1.33×105 M?1 cm?1 at 630 nm), whereas the previously reported triplet photosensitizers based on the spin-orbit charge transfer intersystem crossing (SOCT-ISC) mechanism show absorption in a shorter wavelength range (T=333 μs) was observed for the new dyads. In comparison, the triplet state lifetime of the same chromophore accessed with the conventional heavy atom effect (HAE) is much shorter (τT=1.8 μs). Long triplet state lifetime is beneficial to enhance electron or energy transfer, the primary photophysical processes in the application of triplet PSs. Our approach is based on SOCT-ISC, without invoking of the HAE, which may shorten the triplet state lifetime. We used bisstyrylBodipy both as the electron acceptor and the visible light-harvesting chromophore, which shows red-light absorption. Femtosecond transient absorption spectra indicated the charge separation (109 ps) and SOCT-ISC (charge recombination, CR; 2.3 ns) for BDP-1. ISC efficiency of BDP-1 was determined as ΦT=25 % (in toluene). The dyad BDP-3 was used as triplet PS for triplet-triplet annihilation upconversion (upconversion quantum yield ΦUC=1.5 %; anti-Stokes shift is 5900 cm?1).
- Dick, Bernhard,Dong, Yu,Elmali, Ayhan,Karatay, Ahmet,Zhao, Jianzhang
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- Novel acrylamide/acrylonitrile-tethered carbazoles: Synthesis, structural, biological, and density functional theory studies
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A series of novel carbazolylacrylamides/acrylonitriles 6a-6h were synthesized and their structures were established using various analytical, spectroscopic, and single-crystal X-ray diffraction techniques. The antioxidant evaluation of the target chemical entities 6a-6h was conducted by the DPPH method. The carbazolylacrylonitrile 6h displayed 65.7% radical scavenging activity (IC50 value, 65.08 μM) with respect to standard ascorbic acid. The in vitro cytotoxic activity studies revealed 6e and 6h as promising anticancer molecules against a human pancreatic cancer cell line, i.e., AsPC1. Density functional theory studies of a model chemical entity 6g were performed and the results obtained were compared with those obtained experimentally. The appropriate structure, the corresponding bonding features and the vibrational frequencies for the molecule 6g were determined by employing the DFT-B3LYP method with the 6-311++G(d,p) basis set. The vibrational frequencies of the carbazolylacrylonitrile 6g calculated theoretically were found to be in good agreement with the corresponding experimental results. In addition, the chemical shifts of 1H and 13C of 6g were computed by the gauge independent atomic orbital (GIAO) method and compared with the experimental ones.
- Padmavathy, Krishnaraj,Krishnan, Kannan Gokula,Kumar, Chandran Udhaya,Sathiyaraj, Ethiraj,Sivaramakarthikeyan, Ramar,Lim, Wei-Meng,Mai, Chun-Wai,Ramalingan, Chennan
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- p-TsOH-mediated, Versatile, and Efficient Approach for the Synthesis of Triazolyl-Carbazoles from Nitrovinylcarbazoles and Azide via 1, 3-Dipolar Cycloaddition
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An efficient method for the synthesis of N-alkylated 3-(1-benzyl-1H-1,2,3-triazole-4-yl)-9H-carbazoles (5, 6, 7, 8, 9, 10) and 9-ethyl-3,6-di(1H-1,2,3-triazole-4-yl)-9H-carbazole (13) has been developed from nitroolefines. The effects of catalyst and solvent on these reactions have been investigated. p-TsOH-THF was found to be the best system for this reaction. Various triazolyl-carbazoles were prepared in good to excellent yields.
- Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju
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- Carbazole-based π-conjugated 2,2′-Bipyridines, a new class of organic chromophores: Photophysical, ultrafast nonlinear optical and computational studies
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The developmen of donor-acceptor (D-A) architecture based organic chromophores with large two-photon absorption (2 PA) cross-sections are essential for myriad of applications, ranging from nonlinear microscopy to biomedical imaging. Here, we present the results from a comprehensive study of 2 PA cross-sections of a new series of carbazole mono substituted-π-conjugated-2,2′-bipyridine derivatives with D-π-A architecture, possessing carbazole as the donor moiety and bipyridine core as an acceptor. Further, we have extended the π-conjugation by introducing the phenyl and butoxy substituted phenyl linkers. The fluorescence properties of these D-A chromophores are highly sensitive to solvent polarity and alteration of electron donor functionalities. The relevant computation studies support our experimental results, e.g., a shift in emission maxima and band gaps of the molecules. The third-order nonlinear optical (NLO) properties of the title donor-acceptor (D-A) chromophores demonstrated that 2 PA cross-section values are in the range of 6–39 GM, obtained using ~50 fs (fs) laser pulses at a wavelength of 800 nm. Further, the nonlinear refractive indices (n2) of these chromophores were found to be ~10?14 cm2/W, rendering them potential optical switching candidates since the coefficients were obtained with kHz, fs pulses extracting pure electronic nonlinearities. Based on our experimental findings and theoretical calculations presented in this study, we believe that carbazole-based π-conjugated 2,2′-bipyridines, demonstrated in this work, would be potential ligands to obtain a series of transition metal coordination complexes of interesting physical properties (for example, superior NLO behaviour).
- Bodapati, Ramakrishna,Das, Samar K.,Dey, Gaurav Ranjan,Jose, K. V. Jovan,Krishnakanth, Katturi Naga,Ramteke, Gunjan R.,Rao, S. Venugopal
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- Synthesis and self-assembly of dichalcone substituted carbazole-based low-molecular mass organogel
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We report the synthesis and self-assembly of a new π-conjugated dichalcone substituted carbazole-based low molecular mass organogelator. It could form stable gels in most halogen-aromatic solvents. The transmission electron microscopy (TEM) images revealed that the gel formed fibrous structures with diameter of 50-100 nm, which consisted of several thinner fibers. The FT-IR, UV-vis and XRD results suggested that the H-bonds and π-π interactions were the main driving forces for the formation of the self-assembled gel, in which the U-shaped molecules were stacked into lamellar structures. The fluorescent spectra showed that the emission of the xerogel red-shifted markedly compared with the sol state, which resulted from the aggregation of the molecules. The Royal Society of Chemistry 2006.
- Su, Lihong,Bao, Chunyan,Lu, Ran,Chen, Yulan,Xu, Tinghua,Song, Dongpo,Tan, Changhui,Shi, Tongshun,Zhao, Yingying
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- A Convenient Preparation of Some N-Alkylcarbazoles and N-Alkylacridones
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N-Alkylation of aromatic compounds involving nitrogen heterocycles such as carbazole and acridone with alkyl halide in the presence of caustic solution and benzyl triethyl ammonium chloride (BTEAC) as a phase-transfer catalyst readily proceeded under mild conditions.These results show that this procedure is effective for the preparation of the title compounds in high yields.
- Nishi, Hisao,Kohno, Hisao,Kano, Toshihiro
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- Novel carbazole derivatives with quinoline ring: Synthesis, electronic transition, and two-photon absorption three-dimensional optical data storage
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We designed carbazole unit with an extended π conjugation by employing Vilsmeier formylation reaction and Knoevenagel condensation to facilitate the functional groups of quinoline from 3- or 3,6-position of carbazole. Two compounds doped with poly(methyl methacrylate) (PMMA) films were prepared. To explore the electronic transition properties of these compounds, one-photon absorption properties were experimentally measured and theoretically calculated by using the time-dependent density functional theory. We surveyed these films by using an 800 nm Ti:sapphire 120-fs laser with two-photon absorption (TPA) fluorescence emission properties and TPA coefficients to obtain the TPA cross sections. A three-dimensional optical data storage experiment was conducted by using a TPA photoreaction with an 800 nm-fs laser on the film to obtain a seven-layer optical data storage. The experiment proves that these carbazole derivatives are well suited for two-photon 3D optical storage, thus laying the foundation for the research of multilayer high-density and ultra-high-density optical information storage materials.
- Li, Liang,Wang, Ping,Hu, Yanlei,Lin, Geng,Wu, Yiqun,Huang, Wenhao,Zhao, Quanzhong
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- The synthesis and optical properties of benzothiazole-based derivatives with various π-electron donors as novel bipolar fluorescent compounds
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Novel bipolar benzothiazole-based derivatives with various π-electron donors were synthesized and characterized using 1H and 13C NMR and mass spectrometry; their thermal, optical and electrochemical properties were also investigated. Optoelectronic properties are reported and discussed in terms of the distribution of the highest occupied molecular orbital and the lowest unoccupied molecular orbital and the conjugative pathway between the electron-donating moieties and electron-accepting moieties. The compounds exhibited high fluorescence quantum yield, desirable HOMO levels and high thermal stability. Quantum chemical calculations were used to study optimized ground-state geometry as well as spatial distributions of HOMO and LUMO levels of the compounds.
- Wang, Haiying,Chen, Gang,Xu, Xiaoping,Chen, Hua,Ji, Shunjun
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- Hydrazide-integrated carbazoles: Synthesis, computational, anticancer and molecular docking studies
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A new class of carbazole-based hydrazides 6a-c, synthesized from carbazole by employing a multistep synthetic strategy, has been described. Detailed insight into their structures (6a-c) has been elucidated by UV-Vis, FT-IR and NMR (1H and 13C) spectroscopic studies. Theoretical investigation of the molecules 6a-c has been accomplished utilizing DFT and TD-DFT techniques with the B3LYP/6-311++G(d,p) method. Theoretical findings such as optimized structural, vibrational, and electronic properties, and proton and carbon chemical shifts of the targets 6a-c are in harmony with their experimental results and/or structurally related reported ones. Cytotoxicity of the target hydrazides 6a-c has been evaluated using human pancreatic cancer cells (AsPC1 and SW1990). The hydrazides 6a-c displayed a significant in vitro cytotoxic effect against both the pancreatic cancer cells AsPC1 (concentration that inhibits 50% cell viability, IC50: 3.42 ± 0.41 μM for 6a) and SW1990 (IC50: 22.42 ± 1.40 μM for 6a). The superior binding energy resulting from the in silico molecular docking approach of the hydrazide 6a indicates its greater affinity towards the receptor (binding energy: -8.63 kcal mol-1 and IC50: 475.05 nM). Thus, the hydrazide 6a could serve as a new lead for the development of anticancer agents.
- Krishnan, Kannan Gokula,Ashothai, Pathinettampadi,Padmavathy, Krishnaraj,Lim, Wei-Meng,Mai, Chun-Wai,Thanikachalam, Punniyakoti V.,Ramalingan, Chennan
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- Bodipy-C60 triple hydrogen bonding assemblies as heavy atom-free triplet photosensitizers: preparation and study of the singlet/triplet energy transfer
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Supramolecular triplet photosensitizers based on hydrogen bonding-mediated molecular assemblies were prepared. Three thymine-containing visible light-harvesting Bodipy derivatives (B-1, B-2 and B-3, which show absorption at 505 nm, 630 nm and 593 nm, respectively) were used as H-bonding modules, and 1,6-diaminopyridine-appended C60 was used as the complementary hydrogen bonding module (C-1), in which the C60 part acts as a spin converter for triplet formation. Visible light-harvesting antennae with methylated thymine were prepared as references (B-1-Me, B-2-Me and B-3-Me), which are unable to form strong H-bonds with C-1. Triple H-bonds are formed between each Bodipy antenna (B-1, B-2 and B-3) and the C60 module (C-1). The photophysical properties of the H-bonding assemblies and the reference non-hydrogen bond-forming mixtures were studied using steady state UV/vis absorption spectroscopy, fluorescence emission spectroscopy, electrochemical characterization, and nanosecond transient absorption spectroscopy. Singlet energy transfer from the Bodipy antenna to the C60 module was confirmed by fluorescence quenching studies. The intersystem crossing of the latter produced the triplet excited state. The nanosecond transient absorption spectroscopy showed that the triplet state is either localized on the C60 module (for assembly B-1·C-1), or on the styryl-Bodipy antenna (for assemblies B-2·C-1 and B-3·C-1). Intra-assembly forward-backward (ping-pong) singlet/triplet energy transfer was proposed. In contrast to the H-bonding assemblies, slow triplet energy transfer was observed for the non-hydrogen bonding mixtures. As a proof of concept, these supramolecular assemblies were used as triplet photosensitizers for triplet-triplet annihilation upconversion.
- Guo, Song,Xu, Liang,Xu, Kejing,Zhao, Jianzhang,Kü?ük?z, Betül,Karatay, Ahmet,Yaglioglu, Halime Gul,Hayvali, Mustafa,Elmali, Ayhan
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- Carbazole substituted boron dipyrromethenes
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meso-Substituted BODIPY with N-butylcarbazole (1) was prepared and derivatized. Dibromo BODIPY 2, α-formyl BODIPY 3 and β-formyl BODIPY 4 were synthesized. All compounds were characterized by HRMS, NMR, UV-vis absorption, electrochemical and fluorescence techniques. The crystal structures of BODIPY 1 and its dibromo derivative 2 were also solved. In both the X-ray structures, the dihedral angle between the meso-carbazole group and the dipyrrin plane was decreased, suggesting the increased interaction between the two units. meso-Substitution with the N-butylcarbazole group on the BODIPY core rendered huge Stokes shifts (111-168 nm) and higher quantum yields as compared to meso-aryl BODIPY. An efficient energy transfer from the carbazole unit to the BODIPY core was observed by fluorescence spectroscopy for all the compounds 1-4. CV studies of compounds 1-4 showed anodic shifts of the reduction and oxidation potentials, suggesting that the meso-carbazole group is affecting the electronic properties of the BODIPY core and making them easier to reduce.
- Kesavan, Praseetha E.,Gupta, Iti
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- Intrachain electron and energy transfer in conjugated organometallic oligomers and polymers
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The synthesis of polymers of the type (-Cz-C≡C-PtL 2-C≡C-Cz-X-)n along with the corresponding model compounds (Ph-PtL′2-C≡C-Cz)2-X-, where Cz = 3.3′-carbazole, X = nothing, Cz, or F (2,2′-fluorene), L = PBu 3, and L′ = PEt3 are reported. The electronic spectra (absorption, excitation, emission, and ns-transient spectra) and the photophysics of these species in 2-methyltetrahyrofuran (2MeTHF) at 298 and 77 K are presented. Evidence for singlet electron and triplet energy transfer from the Cz chromophore to the F moiety are provided and discussed in detail. The rate for electron transfer is very fast (>4×1011 s -1), whereas that for triplet-triplet energy transfer is much slower (≈ 103s-1). This work represents a very rare example of studies that address electronic communication in the backbone of a conjugated organometallic polymer.
- Aly, Shawkat Mohammed,Ho, Cheuk-Lam,Fortin, Daniel,Wong, Wai-Yeung,Abd-El-Aziz, Alaa S.,Harvey, Pierre D.
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- Fluorescent carbazolyldithiane as a highly selective chemodosimeter via protection/deprotection functional groups: A ratiometric fluorescent probe for Cd(II)
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A carbazole-based bis-dithiane (1) was rationally constructed in a straightforward manner for the selective and ratiometric fluorescent detection of Cd2+ with the concept of aldehyde group protection/deprotection. The probe showed a ratiometric fluorescent response to Cd2+ with a large emission wavelength shift (>50 nm) and displayed high selectivity for Cd2+ over other metal ions due to distinct deprotection conditions. In addition, a Cd2+-promoted dethioacetalization mechanism was proposed.
- Mahapatra, Ajit Kumar,Roy, Jagannath,Sahoo, Prithidipa
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- Density functional theory study of carbazole dyes: Potential application of carbazole dyes in dye-sensitized solar cells
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Dyes applied in dye synthesized solar cells are an important class of organic compounds. In order to extension novel dyes, three organic dyes (TB-CH, TB-CB and DTB-CB) which contain hexyl and butyl moieties as a branch and thiobarbutiric acid moiety as an electron acceptor, connected by carbazole unit have been studied. We report the synthesis, molecular structures, and study of adsorption of dyes on TiO2 anatase by density functional theory (DFT). Molecular orbital analysis study indicated all dyes can give suitable electron injection from their LUMO orbitals to the TiO2 conduction band. Also, dyes were investigated by UV spectroscopy and cyclic voltammetry (CV). The synthesized dyes were characterized extensively by IR, 1HNMR, 13CNMR, mass spectroscopy and CHN analysis. Results of Photo physical, electrochemical properties and density functional theory investigation indicated TB-CH, TB-CB and DTB-CB have potential for application in dye sensitized solar cell. The adsorption energy of each dye/TiO2 complex was ?1.05, ?1.01 and ?1.00 eV for TB-CH, TB-CB and DTB-CB, respectively.
- Salimi Beni, Alireza,Zarandi, Maryam,Hosseinzadeh, Behzad,Najafi Chermahini
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- Molecular Design of Carbazole-based Dyes and the Influence of Alkyl Substituent on the Performance of Dye-Sensitized Solar Cells
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Carbazole is an alternant polycyclic aromatic hydrocarbon consisting of three fused rings with a large, aromatic system, containing nitrogen atom showing extensive electron delocalization. In this work, carbazole applied as π-conjugated bridge to construct electron donor–π–electron acceptor (D–π–A) organic dyes, where barbutiric acid and thiazolidine-2,4-dione as electron acceptor. The effects of these three acceptors and length of alkyl on the performance of the DSSCs were investigated systematically along with their photophysical and photo electrochemical properties. These series of organic dyes include (B-CH, B-C B, DT-CB, DB-CB). Our investigation indicate among dyes containing butyl as same donor, DT-CB exhibited the maximum overall conversion efficiency of 1.44% and from dyes by deferent electron donor B-CH shows conversion efficiency of 1.47%.
- Beni,Zarandi,Madram,Bayat,Chermahini,Ghahary
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- Synthesis and optical characterization of novel carbazole Schiff bases
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In this study, newly substituted carbazole derivatives of S1; (Z)-4-((9-isobutyl-9H-carbazol-3-ylimino)methyl)phenol, S2; (Z)-9-butyl- N-(2,3,4-trimethoxybenzylidine)-9H-carbazol-3-amine, S3; (Z)-4-((9-octyl-9H-carbazol-3-ylimino)methyl)benzene-1,2-diol and S4; (Z)-3-((9-octyl-9H-carbazol-3-ylimino)methyl)benzene-1,2-diol compounds are synthesized by using condensation reaction between carbazole amines and aromatic aldehydes. All synthesized carbazole Schiff bases are purified by crystallizing from chloroform. The structural and optical characterizations of synthesized compounds are investigated by FT-IR (Fourier Transform-Infrared Spectroscopy), 1H NMR (Proton Nuclear Magnetic Resonance), 13C NMR (Carbon Nuclear Magnetic Resonance), LC-MS (Liquid Chromatography-Mass Spectrometry) and temperature dependent PL (Photoluminescence) measurements. The formations of synthesized Schiff bases were confirmed by FT-IR, NMR and microanalysis. Due to stronger π-conjugation and efficient charge transfer from host material, the broad and complex bands centered at about ～2.16 and ～1.76 eV are observed in PL spectra for all samples. Their relative intensities depend on functional groups associated with the carbazole. These newly synthesized Schiff bases could be considered as an active emissive layer for organic light emitting diodes.
- ?i?ek, Baki,?al???r, ümit,Tavasl?, Mustafa,Tülek, Remziye,Teke, Ali
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- A highly sensitive acidic pH fluorescent probe and its application to E. coli cells
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A new pH fluorescent probe 3-(N-butylcarbazol-3-dicyanovinyl) pyridine (BILE), which has a carbazole structure attached to pyridine, is synthesized for extremely acidic conditions. BILE displays excellent pH-dependent performance with a pKaof 2.93 and responds linearly to minor pH changes in the range of 2.60–3.30, which can be used to quantitatively detect pH value based on regression equation, F = 2495.42 × pH – 6316.28. Moreover, BILE has good selectivity, large Stokes shift (122 nm), sensitivity and short response time. More importantly, BILE has been applied successfully to imaging extreme acidity in E. coli cells, indicating that the probe can afford practical application in biological systems.
- Chao, Jianbin,Wang, Huijuan,Song, Kailun,Li, Zhiqing,Zhang, Yongbin,Yin, Caixia,Huo, Fangjun,Wang, Juanjuan,Zhang, Ting
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- Novel diethynylcarbazole macrocycles: Synthesis and optoelectronic properties
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Diethynylcarbazole macrocycles 1b and 2b have been synthesized by oxidative coupling of appropriate precursors. In particular, macrocycle 2b was prepared by bimolecular Pd-catalyzed oxidative coupling in 35% isolated yield. The spectroscopic properties of these macrocycles and their precursors were measured in detail. The films of these macrocycles by the dipping method and the Langmuir-Blodgett technique were fabricated to study their photoinduced charge-transfer properties. A rapid and steady cathodic photocurrent of these films was produced in a three-electrode cell when irradiated with white light. A possible mechanism of the photoinduced electron-transfer pathway was suggested.
- Zhao, Tianyue,Liu, Zhanxiang,Song, Yabin,Xu, Wei,Zhang, Deqing,Zhu, Daoben
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Read Online
- Novel carbazole-pyridine copolymers by an economical method: Synthesis, spectroscopic and thermochemical studies
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The synthesis, as well as spectroscopic and thermochemical studies of a novel class of carbazole-4-phenylpyridine co-polymers are described. The synthesis was carried out by a simple and cheaper method compared to the lengthy methods usually adopted for the preparation of carbazole-pyridine copolymers which involve costly catalysts. Thus, two series of polymers were synthesized by a modified Chichibabin reaction, i.e., by the condensation of diacetylated N-alkylcarbazoles with 3-substituted benzaldehydes in the presence of ammonium acetate in refluxing acetic acid. All the polymers were characterized by FTIR, 1H NMR, 13C NMR, UV-vis spectroscopy, fluorimetry, TGA and DSC. The weight average molecular masses (Mw) of the polymers were estimated by the laser light scattering (LLS) technique.
- Saeed, Aamer,Irfan, Madiha,Samra, Shahid Ameen
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Read Online
- Activating Versatile Mechanoluminescence in Organic Host–Guest Crystals by Controlling Exciton Transfer
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Mechanoluminescence (ML) materials are attracting increasing interest owing to promising applications in various areas. However, to date, it remains a major challenge to develop a precise and universal route to achieving organic ML materials. Herein, we show that ML can be easily realized in organic piezophotonic host–guest crystals, under conditions in which neither the host nor the guest is ML-active. The experimental and theoretical results reveal that excitons of the host generated by piezoelectricity can be harvested effectively by the guest for light emission, owing to the restraint of intersystem crossing process. Moreover, different host–guest crystals are constructed, wherein the emission color, intensity, color purity, and emission duration of ML can be manipulated. This work deepens our understanding of organic ML generation in piezophotonic host–guest crystals and provides an inspiring principle to design more organic ML materials.
- Chi, Zhenguo,Huang, Qiuyi,Li, Wenlang,Ma, Dongyu,Mao, Zhu,Xu, Chao,Yang, Zhan,Zhang, Xiaoyue,Zhang, Yi,Zhao, Juan
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- Human peripheral blood mononuclear cells targeted multidimensional switch for selective detection of HSO3? anion
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A new ratiometric π-conjugated luminophore with donor-acceptor (D- π- A) network CM {(E)-2-(4-(2-(9-butyl-9H-carbazol-3-yl)vinyl)benzylidine)malononitrile} has been synthesized by malononitrile conjugated carbazole dye with an intervening p-styryl spacer. Here, p-styryl conjugated malononitrile is used as a recognition site for the detection of HSO3? with a fast response time (within 50 s). In a mixed aqueous solution, CM reacts with HSO3? to give a new product 1-(9-butyl-9H-carbazol-3-yl)-2-(4-(2, 2-dicyanovinyl)phenyl)ethane-1-sulfonic acid. The probe exhibits positive solvatofluorochromism with solid state red fluorescence. The restriction of intermolecular rotation of p-styryl conjugated malononitrile unit enhances the typical solid state fluorescence properties. The probe (CM and its corresponding aldehyde CA) also demonstrates a strong solvent dependence yielding blue to green to pink and even red fluorescence in commonly used organic solvents like n-hexane, toluene, diethyl ether (DEE), THF, DCM, Dioxane, CH3CN and MeOH. The chemodosimetric approach of HSO3? selectively takes place at the olefinic carbon exhibiting a prominent chromogenic as well as ratiometric fluorescence change with a 147 nm blue-shift in the fluorescence spectrum. CM can detect HSO3? as low as 1.21 × 10?8 M. Moreover, the CM can be successfully applied to detect intrinsically generated intracellular HSO3? in human peripheral blood mononuclear cells (PBMCs). CM has shown sharp intensities (2628 ± 511.8) when the cells are HSO3? untreated. At green channel (at 486 nm) almost negligible fluorescence intensities are found (423 ± 127.5) for HSO3? untreated samples. However, the green fluorescence (2863 ± 427.5) increases significantly (p 3?. The CM has been effectively utilized for evaluating the bisulfite ions in food samples as well. The concentrations of HSO3? in diluted sugar samples have been determined with the recovery of 97.6–9.12%.
- Bhattacharyya, Maitree,Das, Partha Pratim,Das, Sangita,Ghoshal, Kakali,Mondal, Tapan Kumar,Patra, Lakshman,Thomas, Sabu,Walton, James W.
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- Redox-neutral decarboxylative photocyclization of anthranilic acids
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A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.
- Huang, Huawen,Deng, Kun,Deng, Guo-Jun
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p. 8243 - 8247
(2020/12/29)
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- Design and synthesis of aryl-functionalized carbazole-based porous coordination cages
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A subset of coordination cages have garnered considerable recent attention for their potential permanent porosity in the solid state. Herein, we report a series of functionalized carbazole-based cages of the structure type M12(R-cdc)12 (M = Cr, Cu, Mo) where the functional groups include a range of aromatic substituents. Single-crystal X-ray structure determinations reveal a variety of intercage interactions in these materials, largely governed by pi-pi stacking. Density functional theory for a subset of these cages was used to confirm that the nature of the increased stability of aryl-functionalized cages is a result of inter-cage ligand interactions. This journal is
- Rowland, Casey A.,Lorzing, Gregory R.,Bhattacharjee, Rameswar,Caratzoulas, Stavros,Yap, Glenn P. A.,Bloch, Eric D.
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supporting information
p. 9352 - 9355
(2020/10/02)
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- The aggregation induced fluorescence effect enhanced by a reasonable length of carbon chain
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Six different barbituric acid derivatives using ethyl, propyl, butyl, pentyl, hexyl and heptyl groups as hydrophobic substituents were prepared. Molecular dynamics simulation was carried out to study the effect of different carbon chain lengths on the aggregation-induced emission process. Among the compounds, the CB-5 containing a hexyl substituent exhibited the strongest Aggregation induced emission (AIE) effect, not the CB-6 with longest carbon chain. The aggregates of CB-5 was used to detect the 2, 4, 6-trinitrotoluene (TNT) in aqueous media, exhibiting a maximum quenching constant of 3.1 × 105 M? 1. The paper sensor based on CB-5 showed a superior sensitivity toward TNT both in vapor and solution. This provided a clear strategy for designing compounds that utilize the hydrophobic interaction of long-chain alkyl chains to enhance the AIE effect.
- Zhang, Hanjun,Tao, Furong,Cui, Yuezhi,Xu, Zhen
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- Pd-Catalyzed Intramolecular Chemoselective C(sp2)-H and C(sp3)-H Activation of N-Alkyl- N-arylanthranilic Acids
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A controllable palladium-catalyzed intramolecular C-H activation of N-alkyl-N-arylanthranilic acids has been developed. The methodology allows selective synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones and carbazoles from the same starting materials and palladium catalyst. The selectivity is controlled by the oxidant. Silver oxide promotes C(sp3)-H activation/C-O cyclization to provide 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones, while copper acetate contributes to C(sp2)-H activation/decarboxylative arylation to afford carbazoles. This protocol is demonstrated by its wide substrate scope and good functional group tolerance.
- Hu, Zhe-Yao,Zhang, Yan,Li, Xin-Chang,Zi, Jing,Guo, Xun-Xiang
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supporting information
p. 989 - 992
(2019/05/16)
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- Alkyl Chain Introduction: In Situ Solar-Renewable Colorful Organic Mechanoluminescence Materials
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Mechanoluminescence (ML) materials are environmentally friendly and emit light by utilizing mechanical energy. This has been utilized in light sources, displays, bioimaging, and advanced sensors. Organic ML materials are strongly limited to application by in situ unrepeatable ML. Now, in situ solar-renewable organic ML materials can be formed by introducing a soft alkyl chain into an ML unit. For the first time, the ML from these polycrystalline thin films can be iteratively produced by simply recrystallizing the fractured crystal in situ after a contactless exposure to sunlight within a short time (≤60 s). Additionally, their ML color and lifetime can be also easily tuned by doping with organic luminescent dyes. Therefore, large-area sandwich-type organic ML devices can be fabricated, which can be repeatedly used in a colorful piezo-display, visual handwriting monitor, and sensitive optical sensor, showing a lowest pressure threshold for ML of about 5 kPa.
- Li, Wenlang,Huang, Qiuyi,Mao, Zhu,Li, Qi,Jiang, Long,Xie, Zongliang,Xu, Rui,Yang, Zhiyong,Zhao, Juan,Yu, Tao,Zhang, Yi,Aldred, Matthew P.,Chi, Zhenguo
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supporting information
p. 12727 - 12732
(2018/09/14)
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- A containing carbazolyl ultraviolet absorbent and its preparation method (by machine translation)
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The invention discloses a containing carbazolyl ultraviolet absorbent and its preparation method, the ultraviolet absorbent of the chemical name is 3, 6 - di (2 - bromo - 5 - thienyl) - 9 - butyl carbazole, molecular formula is C24 H19 NBr2 S2 , It can at the same time keeping the light absorption performance of quenching fluorescence, the product is maintained colorless transparent characteristics. (by machine translation)
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Paragraph 0009; 0010; 0011
(2018/07/30)
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- An optical initiator containing double-carbazole thiophene dimethyl oxime acetate, preparation method and application thereof (by machine translation)
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The invention relates to an optical initiator containing double-carbazole thiophene dimethyl oxime acetate preparation method. Carbazole with 1 - bromo butane in potassium hydroxide, DMSO system reaction to obtain the intermediate I; intermediate I with nitric acid nitration reaction to obtain the intermediate II; in under the catalytic action of aluminum trichloride, intermediate II with 2, 5 - II (chloroformyl) thiophene generating Friedel - Crafts reaction to obtain the intermediate III; in mixed solvent of methanol under the conditions of water -, intermediate III reacted with hydroxylamine hydrochloride to obtain intermediate IV, the final intermediate IV with acetic anhydride reaction to obtain the target compound photoinitiator containing double-carbazole thiophene dimethyl oxime acetate. This preparation method, the operation is simple, the process is advanced, the solvent can be recycled, to industrial production. (by machine translation)
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Paragraph 0008; 0034; 0036
(2018/09/28)
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- Singlet-singlet energy transfer in carbazole-porphyrin dyads and triads
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Donor-π-Acceptor (D-π-A) type carbazole-porphyrin dyads and triads were synthesized in good yields through palladium catalyzed coupling reactions. The length of the spacer between the D (carbazole) and A (porphyrin) was varied from “phenylethyne” to “ethyne linkage”. The effect of the linker length on the spectral properties of these D-π-A dyads and triads was studied. The N-butyl-3-ethynyl-carbazole was coupled with different porphyrins bearing either one or two meso-p-iodophenyl group/meso-bromo groups using palladium catalyst. All the dyads and triads were characterized by MALDI-MS, NMR, UV–vis absorption, fluorescence and cyclic voltammetry techniques. The S1 emission dynamics were analyzed by time-resolved spectroscopy (TCSPC); an efficient energy transfer up to 84% was observed from donor groups to the porphyrin core. Electrochemical studies revealed that, compounds having freebase porphyrin components are difficult to reduce as indicated by the cathodic shift in their reduction potentials. On the contrary, the compounds having zinc porphyrin components are easy to reduce as reflected by the anodic shift in their reduction potentials. The lowest HOMO-LUMO gap was found for the dyad which has short linker between D and A.
- Balsukuri, Naresh,Gupta, Iti
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p. 223 - 233
(2017/05/29)
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- A Green Synthesis of 2-Amino-4-(9H-carbazole-3-yl)thiophene-3-carbonitriles by a Step-wise and One-pot Three-component Gewald Reaction
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An eco-friendly method has been developed for the synthesis of 2-amino-4-(9H-carbazole-3-yl)thiophene-3-carbonitriles from preliminary carbazole (1) through an intermediate of 2-(1-(9H-carbazole-3-yl)ethylidene)malononitriles using the Knoevenagel condensation followed by the Gewald reaction. On the other hand, the target compounds could also be prepared in a one-pot three-component manner by treating equimolar quantities of 1-(9H-carbazole-3-yl)ethanone (3), malononitrile, and elemental sulfur. The merits of this preparation are mild reaction conditions. The Gewald reaction is executed with inorganic base NaHCO3 (H2O) in tetrahydrofuran, easy work-up procedure with good yields.
- Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju
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p. 2471 - 2482
(2017/07/25)
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- Effect of Thiophene Spacer Position in Carbazole-Based Dye-Sensitized Solar Cells on Photophysical, Electrochemical and Photovoltaic Properties
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The synthesis, photophysical and electrochemical properties, and photovoltaic performances in dye-sensitized solar cells (DSSCs) of five new metal-free organic sensitizers with a carbazole moiety as the electron donor are reported. The compounds contain a thiophene at various positions and a cyanoacrylic acid unit as the electron acceptor. The position of the thiophene moiety affected both the photophysical and electrochemical properties, leading to conversion efficiencies of 1.44 to 4.57 % under AM 1.5 solar conditions (100 mW cm–2). The best performance and longest electron lifetime were found when a thiophene was located on both donor and acceptor sites. The DSSC showed a short-circuit current (Jsc) of 8.59 mA/cm2, an open-circuit photovoltage (Voc) of 0.75 V, and a fill factor (FF) of 0.71. The position of the π-conjugated bridges not only affects the absorption spectra and the energy levels of the sensitizers, but also adjusts the electron lifetime.
- Samae, Ruslan,Surawatanawong, Panida,Eiamprasert, Utt,Pramjit, Songyos,Saengdee, Laksana,Tangboriboonrat, Pramuan,Kiatisevi, Supavadee
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p. 3536 - 3549
(2016/07/28)
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- A very acidic pH carbazole class fluorescence probe and its preparation method and application (by machine translation)
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The invention discloses a very acidic pH carbazole class fluorescence probe and its preparation method and application. The fluorescent probe is 3 - (9 - butyl carbazole - 3 - cyanoacetate vinyl) pyridine. Its preparation method: the carbazole, DMSO/KOH bromine butane dissolved in the mixed solution, stirring and heating, generating 9 - butyl carbazole; to DMF as solvent, POCl3 With the 9 - butyl carbazole reaction, to obtain 3 - formyl - 9 - butyl carbazole; then the obtained 3 - formyl - 9 - butyl carbazole and 3 - pyridine base second grade nitrile mixed in methanol, tertiary butanol potassium, filtering, drying, can get the yellow solid product. The probe has lower pKa Value, to the H+ Has revealed the high sensitivity, selectivity and stability is good, and the detection process is simple, fast, accurate detection results and the like. In addition, by combining a laser confocal scanning microscopy, the fluorescent probe can be used for extremely acidic environment in the biological sample in the detection of pH changes. (by machine translation)
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Paragraph 0028; 0029
(2017/04/25)
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- A measuring-ClO diphenylenimine kind of fluorescent probe and its preparation method and application (by machine translation)
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The invention discloses a measuring ClO ? diphenylenimine kind of fluorescent probe and its preparation method and application. Process for the preparation of the fluorescent probe: will diphenylenimine, DMSO/KOH bromine butane in dissolved in the mixed solution, stirring and heating, to produce the 9 [...] butyl diphenylenimine; in DMF as the solvent, POCl 3 and the resultant reaction, to obtain the 3 [...] formyl -9 the butyl [...] diphenylenimine; and the 3 [...] pyridine acetonitrile mixed in the methanol, butanol joins uncle potassium, to produce the 1 [...] methyl -3 the [...] (9 the [...] butyl diphenylenimine -3 the vinyl [...] ) pyridine; product dissolved in HCCl 3 in, adding CH 3 I, filtering, drying, orange solid product can be obtained. This probe against ClO ? display a high sensitivity and selectivity, in detecting ClO ? of ions Stocks exhibits a large displacement, and the detection process is simple and convenient, quick, accurate detection results. By combining laser confocal scanning microscopy, can also obtain the novel fluorescent probe in the fluorescence imaging in living cells. (by machine translation)
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Paragraph 0014; 0033; 0034
(2017/05/12)
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- Visible light-harvesting tricarbonyl Re(I) complex: Synthesis and application in intracellular photodynamic effect and luminescence imaging
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Re(I) tricarbonyl rhenium(I) complexes attracted much attention owing to the good cellular uptake ability and rich photophysical properties. However, normally Re(I) complexes show short triplet state lifetime and weak absorption in the visible spectra region, and the absorption wavelength usually is shorter than 450 nm. These features are detrimental to the applications of Re(I) complexes in the areas such as photodynamic therapy (PDT) and luminescence bioimaging. Herein, a novel tricarbonyl rhenium(I) complex Re-1 with strong visible light-absorbing ability (624 nm, ε=5.69×104 L/(mol cm)), long-lived triplet excited state (τ T=448.9 μs) and moderate fluorescence quantum yield (Φ F=41.6%) was prepared. The photophysical properties of Re-1 were studied with steady state UV-Vis absorption and luminescence spectroscopies, nanosecond transient absorption spectroscopy, as well as DFT/TDDFT calculations. Re-1 was used for intracellular PDT and luminescence imaging studies. The results indicate that Re-1 shows low dark toxicity, but it is able to kill cancer cells on illumination with 635 nm LED.
- Zhong, Fangfang,Yuan, Xiaolin,Zhao, Jianzhang,Wang, Quan
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- Design, synthesis, and biological evaluation of novel carbazole aminothiazoles as potential DNA-targeting antimicrobial agents
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A series of novel carbazole aminothiazoles as a new type of antimicrobial agents were designed, synthesized and characterized by 1H NMR, 13C NMR, IR, MS and HRMS spectra. Some of the carbazole aminothiazoles exhibited good antimicrobial activities; particularly, heptyl-derived carbazole aminothiazole 4f could effectively inhibit the growth of MRSA with an MIC value of 4 μg mL-1, which was superior to the reference drugs Chloromycin and Norfloxacin. Moreover, cytotoxicity investigation indicated that bioactive compound 4f did not exhibit cytotoxicity to Hep-2 cells within its MIC against MRSA. Preliminary interactive investigation revealed that compound 4f could effectively intercalate into calf thymus DNA to form 4f-DNA complexes which might block DNA replication and thus exert antimicrobial activities. In addition, the binding behavior of compound 4f to DNA revealed that compound 4f could interact with DNA by hydrogen bonds and electrostatic interactions.
- Addla, Dinesh,Wen, Si-Qi,Gao, Wei-Wei,Maddili, Swetha Kameswari,Zhang, Ling,Zhou, Cheng-He
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p. 1988 - 1994
(2016/10/22)
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- Highly efficient phosphorescent materials based on Ir(III) complexes-grafted on a polyhedral oligomeric silsesquioxane core
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A new iridium(iii) complex containing a coumarin derivative as the cyclometalated ligand (L) and a carbazole-functionalized β-diketonate (Cz-acac-allyl) as the ancillary ligand, namely, Ir(iii) bis(3-(pyridin-2-yl)coumarinato-N,C4)(1-(9-butyl-9H-carbazol-3-yl)hept-6-ene-1,3-dionato-O,O) [Ir(L)2(Cz-acac-allyl)], was firstly synthesized as the emissive iridium(iii) complex. Then three new phosphorescent polyhedral oligomeric silsesquioxane (POSS) materials, consisting of the emissive Ir(iii) complex and carbazole moieties covalently attached to a polyhedral oligomeric silsesquioxane (POSS) core were successfully synthesized by hydrosilylation reaction in the presence of platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane (Pt-dvs) as the catalyst. These phosphorescent POSS materials offer many advantages including amorphous properties, good thermal stabilities, and good solubility in common solvents, and high purity via column chromatography. The photoluminescence spectra of the POSS materials in solution and in the solid state indicate a reduction in the degrees of interactions among the Ir(iii) complex units and concentration quenching due to the bulky POSS core. Solution processed light-emitting devices based on these phosphorescent POSS materials exhibit a maximum external quantum efficiency (EQE) of 9.77%.
- Yu, Tianzhi,Xu, Zixuan,Su, Wenming,Zhao, Yuling,Zhang, Hui,Bao, Yanjun
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p. 13491 - 13502
(2016/09/04)
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- Novel metal-free organic dyes possessing fused heterocyclic structural motifs for efficient molecular photovoltaics
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Reported herein are six novel metal free organic dyes such as PCA1-PCA3 and PCTA1-PCTA3 featuring fused heterocyclic structural motifs such as phenothiazine and alkylcarbazole. Photophysical/electrochemical properties and nanocrystalline TiO2 based dye-sensitized solar cell performance of the same have been investigated. Electronic distribution within the molecules has been determined through a computational approach. The overall power conversion efficiencies of the devices with the utilization of dyes PCA1-PCA3 and PCTA1-PCTA3 as sensitizers ranges between 4.67 and 8.08%. The novel dyes possessing cyanoacrylic acid as electron acceptor, PCA1-PCA3, exhibit higher power conversion efficiency, short-circuit current, open-circuit voltage, and electron lifetime those with thioxothiazolidinylacetic acid, PCTA1-PCTA3, as the same. Of the devices fabricated by employing the new metal-free organic sensitizers, that with the dye PCA2 exerted a power conversion efficiency (PCE, η) of 8.08% with a short circuit current density (JSC) of 16.45 mA cm-2, an open circuit voltage (VOC) of 735 mV and a fill factor (ff) of 0.68; this PCE is the highest amongst the devices fabricated.
- Karuppasamy, Ayyanar,Stalindurai, Kesavan,Peng, Jia-De,Ho, Kuo-Chuan,Ramalingan, Chennan
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p. 30105 - 30116
(2016/11/17)
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- Novel carbazole-based aggregation-induced emission-active gold(I) complexes with various mechanofluorochromic behaviors
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A series of novel carbazole-based mono- and dinuclear gold(I) complexes with various lengths of alkyl chains were synthesized and characterized using nuclear magnetic resonance spectroscopy, elemental analysis and single crystal X-ray diffractometry. Their aggregation-induced emission characteristics were investigated by ultraviolet/visible and photoluminescence spectroscopy. Their solid-state mechanochromic luminescence behavior was also studied by photoluminescence spectroscopy. All gold(I) complexes based on a carbazole scaffold structure exhibited excellent aggregation-induced emission properties. Luminogens 1 and 2 showed reversible mechanochromism phenomena involving luminescent color transformation from yellow-green to green. Luminogens 3 and 4 exhibited switchable mechanochromic luminescence behavior involving fluorescent color change from colorless to green. The solid-state fluorescence of luminogens 5 and 6 can be switched between weak and strong fluorescence by mechanical force stimulus, and this conversion is irreversible.
- Chen, Zhao,Li, Zheng,Hu, Fang,Yu, Guang-Ao,Yin, Jun,Liu, Sheng Hua
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p. 169 - 178
(2015/11/17)
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- Carbazole-bridged double D-A dye for efficient dye-sensitized solar cell
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A di-anchoring organic dye based on an acceptorπ spacerdonorsecondary donordonorπ spacer acceptor structural motif has been synthesized and used as a sensitizer for dye-sensitized solar cells (DSSCs). The new synthetic approach uses two π spacers, two acceptors and two different donors such as arylamino and carbazole units. The double donoracceptor dye CBZ-3 is linked by a carbazole unit as a secondary donor which increases the donoracceptor strength of the dye and proved to increase the η and Jsc values of the photovoltaic cell compared to the corresponding mono-anchoring system CBZ-2 and the monodonor dye CBZ-1. With the non-planar structure of the arylamino group and the alkyl chains which efficiently prevent the formation of the dye aggregates, the dye exhibited a high open-circuit photovoltage (Voc) of 650 mV, a short-circuit photocurrent density (Jsc) of 7.20 mA cm-2 and the solar energy-to-electricity conversion efficiency (η) of 3.23%.
- Pramjit, Songyos,Eiamprasert, Utt,Surawatanawong, Panida,Lertturongchai, Pattida,Kiatisevi, Supavadee
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- Synthesis and Characterization of Carbazole-Linked Porphyrin Tweezers
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Herein the synthesis, spectroscopic characterization, two-photon absorption and electrochemical properties of 3,6-disubstituted carbazole tweezers is reported. A dimer resulting from a Glaser homocoupling was isolated during a Sonogashira coupling reaction between a diethynyl-carbazole spacer and a 5-bromo-triarylporphyrin and the properties of this original compound were compared with the 3,6-disubstituted carbazole bisporphyrin tweezers. The dyads reported herein present a two-photon absorption maximum at 920nm with two-photon absorption cross-section in the 1200GM range. Despite a strong linear absorption in the Soret region and moderate fluorescence quantum yield, they both lead to a high brightness reaching 30000m-1cm-1.
- Chang, Yi,Michelin, Clment,Bucher, Lo,Desbois, Nicolas,Gros, Claude P.,Piant, Sbastien,Bolze, Frdric,Fang, Yuanyuan,Jiang, Xiaoqin,Kadish, Karl M.
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p. 12018 - 12025
(2015/08/18)
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- Synthesis and luminescence properties of nine novel carbazolyl diacylhydrazone Schiff-bases
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Nine novel carbazolyl diacylhydrazone Schiff-bases were synthesized by alkylation, F-C acylation and condensation reactions starting from carbazole and hydrazide. The title Schiff-bases were characterized by 1H NMR, MS, IR and elemental analysis. The synthetic conditions were optimized, and the best yield of the title Schiff-bases was up to 92.3%. The relationships between the luminescence properties and the structures of the title Schiff-bases were studied. The results showed that the introduction of the Naphthalene-2-yloxy could form great plane conjugate structure to improve their luminescence properties.
- Wu, Limin,Wu, Panliang,Guo, Dongcai,Fu, Wenqiang,Li, Dong,Luo, Tao
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- An efficient ultrasound-assisted synthesis of n-alkyl derivatives of carbazole, indole, and phenothiazine
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Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.
- Zhao, Sanhu,Kang, Jin,Du, Yuting,Kang, Jingyan,Zhao, Xiaoni,Xu, Yinfeng,Chen, Ruixi,Wang, Qianqian,Shi, Xitao
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supporting information
p. 683 - 689
(2014/06/10)
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- Specific Cu(II) detection using a novel tricarbazolyl-tristriazolotriazine based on photoinduced charge transfer
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Tricarbazolyl-tristriazolotriazine, a novel Cu(ii)-sensing and selective fluorescent sensor, was designed and synthesised on the basis of the mechanism of photoinduced charge transfer. The synthesised compound exhibits highly sensitive and significant fluorescence decline response towards Cu2+ over other metal ions, with a detection limit of 0.2 μM in THF-H2O (9 : 1, v/v) at neutral pH. Its optical, thermal, electrochemical and morphological properties were studied. The results demonstrate that the compound has high relative fluorescence quantum yield (ΦF = 0.99) in xylene solution, excellent thermal stability (Td = 325 °C, T g = 99.9 °C), wide energy gap (Eg = 4.09 eV), desirable triplet energy (ET = 2.98 eV) and the highest occupied molecular orbital energy (-5.67 eV). Morphological investigation showed that the compound easily forms ribbon-like microstructures. This journal is the Partner Organisations 2014.
- Zhao, He,Wang, Yongtao,Liu, Zhiyong,Dai, Bin
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p. 13161 - 13166
(2014/04/03)
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- Synthesis, structure, photo- and electro-luminescence of an iridium(iii) complex with a novel carbazole functionalized β-diketone ligand
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A new iridium complex containing coumarin derivative as a cyclometalated ligand (1L) and a carbazole-functionalized β-diketonate ( 2L) as the ancillary ligand, namely, Ir(iii)bis(3-(pyridin-2-yl) coumarinato-N,C4)(1-(9-butyl-9H-carbazol-3-yl)-4,4,4-trifluoro- butane-1,3-dionato-O,O) (Ir(1L)2(2L)), was synthesized. The crystal structure of Ir(1L)2( 2L) was determined via combined wide angle X-ray diffraction (WAXD) and transmission electron microscopy (TEM), which showed π-π the interactions of Ir(1L)2(2L) molecules stacking along the crystal axes. The doped light-emitting diodes using this novel Ir(1L)2(2L) complex as the phosphorescent dopant were fabricated. At a Ir(1L)2(2L) concentration of 6.0 wt%, a green-yellow emitting OLED was achieved with a maximum external quantum efficiency (EQE) of 6.11% and a maximum luminous efficiency of 22.55 cd A-1 at the current density of 6.06 mA cm -2, and a maximum luminance of 6653 cd m-2 at 10.7 V. Furthermore, two reference complexes Ir(1L)2(acac) and Ir(1L)2(TTA) were also used as emitters to fabricate OLED devices with the same device configuration. The maximum luminous efficiency of Ir(1L)2(acac) doped device was measured to be 20.04 cd A-1 at 2.15 mA cm-2 (10.0 wt%), while the doped device of Ir(1L)2(TTA) had a maximum luminous efficiency of 16.59 cd A-1 at 1.36 mA cm-2. The better performances of Ir( 1L)2(2L) doped devices could be largely attributed to an improved hole-transporting property due to the introduction of the carbazole moiety. The Royal Society of Chemistry 2014.
- Yu, Tianzhi,Cao, Yan,Su, Wenming,Zhang, Chengcheng,Zhao, Yuling,Fan, Duowang,Huang, Mingjun,Yue, Kan,Cheng, Stephen Z. D.
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p. 554 - 562
(2014/01/06)
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- Two novel six-coordinated cadmium(ii) and zinc(ii) complexes from carbazate β-diketonate: Crystal structures, enhanced two-photon absorption and biological imaging application
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To explore the photophysical properties of coordination compounds with enhanced two-photon absorption, two novel six-coordinated metal complexes (ML2, M = Cd(ii), Zn(ii)) from carbazole β-diketone ligand (HL = 4,4,4-trifluoro-1-(9-butylcarbazole-3-yl)-1,3-butanedione) were prepared and fully characterized. Their crystal structures were determined by X-ray diffraction analysis. Both variable temperature 1H NMR spectra and MALDI-TOF mass spectrometry proved that the coordination compounds exhibit good stability in solution. The results of time-dependent density functional theory (TD-DFT) calculations indicated that the complexation of the ligands with metal ion extends the electronic delocalization in the coordination compounds, leading to enhanced two-photon absorption. The photophysical properties for the coordination compounds were identified relying on both experimentally and theoretically studies. Finally, confocal microscopy and two-photon microscopy fluorescent imaging of HepG2 cells labeled with the Zn(ii) complexe revealed its potential applications as a biological fluorescent probe.
- Nie, Cuiyun,Zhang, Qiong,Ding, Hongjuan,Huang, Bei,Wang, Xinyan,Zhao, Xianghua,Li, Shengli,Zhou, Hongping,Wu, Jieying,Tian, Yupeng
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p. 599 - 608
(2014/01/06)
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- BODIPY triads triplet photosensitizers enhanced with intramolecular resonance energy transfer (RET): Broadband visible light absorption and application in photooxidation
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Resonance energy transfer (RET) was used to enhance the light absorption in triad triplet photosensitizers to access strong and broadband absorption in visible region (from 450-750 nm). This strategy was demonstrated by preparation of (BODIPY)2-diiodo-aza-BODIPY triad (B-2) and (carbazole-styryl BODIPY)2-diiodo-aza-BODIPY triad (B-3), in which the energy donor (BODIPY or styryl-BODIPY) and the energy acceptor (aza-BODIPY, also as the spin converter) parts were connected by click chemistry. Both the energy donors and the energy acceptors show strong absorption in the visible spectral region, but at different wavelengths, therefore the triads show broadband absorption in visible spectra region, e.g. the two major absorption bands of B-3 are located at 593 nm and 683 nm, with ε up to 220 000 M-1 cm-1 and 81 000 M-1 cm-1, respectively. For comparison, a reference compound with only diiodo-aza-BODIPY as the light-harvesting unit was prepared (B-1), which shows only one major absorption band in visible spectral region. Fluorescence studies indicated intramolecular energy transfer for these BODIPY hybrids, a conclusion which is supported by the femtosecond time-resolved transient absorption spectroscopy. Nanosecond transient absorption spectra show that triplet excited states of the dyad and the triad are localized on the iodo-aza-BODIPY part. The compounds were used as triplet photosensitizers for singlet oxygen (1O2) mediated photooxidation of 1,5-dihydroxylnaphthalene and the photosensitizing ability of the new triplet photosensitizers are more efficient than the mono-chromophore based triplet photosensitizers. The molecular design rationale of these RET-enhanced multi-chromophore triplet photosensitizer is useful for development of efficient triplet photosensitizers and for their applications in photocatalysis, photodynamic therapy, photovoltaics and upconversion.
- Guo, Song,Ma, Lihua,Zhao, Jianzhang,Kuecuekoez, Betuel,Karatay, Ahmet,Hayvali, Mustafa,Yaglioglu, H. Gul,Elmali, Ayhan
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p. 489 - 500
(2014/01/17)
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- Optimizing the photovoltaic performance of thiocyanate-free ruthenium photosensitizers by structural modification of C^N cyclometalating ligand in dye-sensitized solar cells
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Five new thiocyanate-free ruthenium(II) complexes with different electron-donating functionalized cyclometalating ligands C^N were synthesized, characterized and applied as photosensitizers in dye-sensitized solar cells (DSSCs). Their photophysical, electrochemical, thermal and photovoltaic properties have been investigated and density functional theory (DFT) calculations have been carried out on these dyes. These dyes exhibit good thermal stability with the onset decomposition temperature at 5% weight-loss (Td) of around 330 °C. The DSSC device using the Ru(II) dye with the 9-tolylcarbazole chromophore exhibited the highest power conversion efficiency (η) up to 3.39%, with a short-circuit photocurrent density (Jsc) of 8.06 mA cm-2, an open-circuit photovoltage (Voc) of 0.62 V and a high fill factor (ff) of 0.68 under illumination of an AM 1.5 solar cell simulator.
- Siu, Chi-Ho,Ho, Cheuk-Lam,He, Jian,Chen, Tao,Majumda, Poulomi,Zhao, Jianzhang,Li, Hua,Wong, Wai-Yeung
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- Synthesis of carbazoles via one-pot copper-catalyzed amine insertion into cyclic diphenyleneiodoniums as a strategy to generate a drug-like chemical library
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Carbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by cop- per(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfon amides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT-22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.
- Zhu, Daqian,Liu, Qi,Luo, Bingling,Chen, Meihui,Pi, Rongbiao,Huang, Peng,Wen, Shijun
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p. 2172 - 2178
(2013/10/01)
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- Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
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Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease.
- Zhu, Daqian,Chen, Meihui,Li, Min,Luo, Bingling,Zhao, Yang,Huang, Peng,Xue, Fengtian,Rapposelli, Simona,Pi, Rongbiao,Wen, Shijun
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- Mastering tricyclic ring systems for desirable functional cannabinoid activity
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There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain and other indications. In continuation of our ongoing program aiming for the development of new small molecule cannabinoid ligands, we have synthesized a novel series of carbazole and γ-carboline derivatives. The affinities of the newly synthesized compounds were determined by a competitive radioligand displacement assay for human CB2 cannabinoid receptor and rat CB1 cannabinoid receptor. Functional activity and selectivity at human CB1 and CB2 receptors were characterized using receptor internalization and [35S]GTP-γ-S assays. The structure-activity relationship and optimization studies of the carbazole series have led to the discovery of a non-selective CB1 and CB2 agonist, compound 4. Our subsequent research efforts to increase CB2 selectivity of this lead compound have led to the discovery of CB2 selective compound 64, which robustly internalized CB2 receptors. Compound 64 had potent inhibitory effects on pain hypersensitivity in a rat model of neuropathic pain. Other potent and CB2 receptor-selective compounds, including compounds 63 and 68, and a selective CB1 agonist, compound 74 were also discovered. In addition, we identified the CB2 ligand 35 which failed to promote CB2 receptor internalization and inhibited compound CP55,940-induced CB2 internalization despite a high CB2 receptor affinity. The present study provides novel tricyclic series as a starting point for further investigations of CB2 pharmacology and pain treatment.
- Petrov, Ravil R.,Knight, Lindsay,Chen, Shao-Rui,Wager-Miller, Jim,McDaniel, Steven W.,Diaz, Fanny,Barth, Francis,Pan, Hui-Lin,Mackie, Ken,Cavasotto, Claudio N.,Diaz, Philippe
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p. 881 - 907
(2013/11/19)
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- A photoactive basket-like metal-organic tetragon worked as an enzymatic molecular flask for light driven H2 production
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A photoactive basket-like metal-organic tetragon Ce-ZL that contained a carbazole photosensitizer was developed to capture the biomimetic [FeFe]-H 2ases for light driven H2 production. The system exhibited enzymatic behaviour and its activity was inhibited by the encapsulation of ATP.
- He, Cheng,Wang, Jian,Zhao, Liang,Liu, Tao,Zhang, Jing,Duan, Chunying
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supporting information
p. 627 - 629
(2013/02/23)
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