- Synthesis, characterization and DFT study of new anthracene-based semiconducting polyethers for OLED application
-
New soluble semiconducting anthracene-based polyethers (An-BPS and An-TDP) were synthetized via the Williamson polycondensation of 9,10-dichloromethylanthracene with 4,4′-thiodiphenol (TDP) and bisphenol S (BPS), respectively. The polymers were investigated by density functional theory (DFT): the structural and optoelectronic properties, frontier molecular orbitals (HOMO/LUMO), as well as the infrared, absorption and fluorescence spectra were discussed. The polyethers structures were confirmed by NMR and FTIR spectroscopies, revealing good agreements between experimental and theoretical results. Quasi-identical absorption and blue emission properties were obtained for both polymers in dilute solutions, with a higher fluorescence efficiency for An-BPS. The cyclic voltammetry analysis of these electrochemically active materials showed a higher electron affinity for An-BPS and a lower ionization potential for An-TDP. The DFT calculations showed that the HOMO/LUMO frontier energy distributions are confined on the anthracene moiety in An-BPS. However in An-TDP, the LUMO distribution is localized on anthracene group, while the HOMO is on the TDP unit. The electric behavior of organic light-emitting diodes (OLEDs) based on these macromolecular structures has been investigated via numerical simulation using Silvaco TECAD software. Good electrical properties are estimated, with a low turn on voltages of 3.1 V and 2.9 V for An-TDP and An-BPS, respectively. However, An-BPS showed improved current conductivity, which makes it a good candidate for OLEDs.
- Mahmoudi, Chaima,Chouk, Rihab,Baatout, Khouloud,Jaballah, Nejmeddine Smida,Khalfaoui, Mohamed,Majdoub, Mustapha
-
-
- Kinetic Stabilization of Blue-Emissive Anthracenes: Phenylene Bridging Works Best
-
In attempts at kinetically stabilizing blue-emissive anthracenes, a series of 9,10-diaryl substituted derivatives were tested for their photochemical and photooxidative persistence. A major breakthrough in light fastness comes from a new bis-meta-terpheny
- Nathusius, Marvin,Sleeman, Daniel,Pan, Junyou,Rominger, Frank,Freudenberg, Jan,Bunz, Uwe H. F.,Müllen, Klaus
-
supporting information
p. 16606 - 16610
(2021/10/16)
-
- Discrete Platinum(II) Metallacycles with Inner- and Outer-Modified 9,10-Distyrylanthracene: Design, Self-Assembly, and Luminescence Properties
-
To completely unravel the relationship between structures and luminescence properties of inner- and outer-modified metallacycles, two rhombic metallacycles S1 and S2 with 9,10-distyrylanthracene (DSA) were constructed herein via the design of DSA moieties on the inside or outside of metallacycles. Similar building blocks of the two metallacycles led to the same emission wavelengths in a dilute solution. In contrast, their fluorescence emissions in the aggregation and solid states were significantly different and revealed interesting emission behaviors from structures with inner- and outer-modified design. Finally, based on their luminescence properties, a tunable solid-state fluorescence emissive material was easily obtained by the mixing of two supramolecules in different ratios. This unique design suggested that the modified position of fluorophores exerts a key impact on the adjustment of luminescence from a dilute solution to the aggregated state and will be of great significance for the development of luminescent materials based on supramolecules.
- Li, Meng,Pan, Guocui,Shi, Junjuan,Tian, Wenjing,Tong, Hui,Wang, Ming,Xu, Bin,Yu, Hao
-
supporting information
(2022/03/27)
-
- Design, synthesis and imaging of a novel mitochondrial fluorescent nanoprobe based on distyreneanthracene-substituted triphenylphosphonium salt
-
Targeting and monitoring the dynamics of mitochondria are of great significance because mitochondria are involved in a variety of physiological and pathological processes. For achieving this purpose, highly sensitive, photostable, tolerance and specific fluorescent probe is necessary. To obtain a superior mitochondrial fluorescent probe, (4-distyreneanthracenoxybutyl) bis(triphenylphosphonium) bromide (DSA-TPP) with aggregation-induced emission (AIE) characteristic was designed and synthesized for mitochondrial targeting. DSA-TPP dots with high fluorescence quantum yield (Φ = 17.9) and small particle size (8 nm) can be easily prepared by self-assembly formation. DSA-TPP dots had the ability of lightning mitochondria in living cells with high brightness, superior photostability and strong tolerance to cell environment change.
- Zhang, Yan,Jiang, Rui,Jiang, Hongbo,Xia, Qinglian,Wang, Yuting,Xiong, Lulu,Xiang zhou,Hu, Lianzhe,Qi, Wenjing
-
-
- Crystallographic and spectroscopic analysis of 9,10-bis-alkyl imidazolium anthracene hexatungstate supramolecular complexes
-
This article describes the ionic and supramolecular association of bis-dialkyl imidazolium anthracene dications with hexametalate cluster anions. In the relevant compounds, the length of the alkyl chain was varied to observe its effect on the crystal packing. Despite the endothermicity in the crystals due to structural incompatibility between planar anthracene and spherical polyoxometalate ion, packing stability is attained by coulombic interaction together with the supramolecular interactions between the components. The nature of supramolecular interactions depends on the number of carbon atoms in the alkyl chain in the organic counterparts of the crystals which ultimately modifies the packing pattern.
- Annapareddy, Gayatri,Mubeena, Shaik,N, Meghana,Sarma, Monima
-
-
- A cationic on-off fluorescent sensor with AIE properties for heparin and protamine detection
-
In this research, a distyryl-anthracene derivative (DSAI) with two quaternary ammonium groups was synthesized. It emitted strong yellow-green fluorescence after aggregating with heparin through electrostatic attraction. In the presence of protamine, the fluorescence of DSAI remarkably quenched because of the greater affinity between heparin and protamine. Based on the change of fluorescence signal, a highly sensitive and selective method is successfully constructed to detect heparin and protamine. The DSAI sensor toward heparin showed a broad linear range (0.1 to 1.1 μg mL?1) and a low detection limit (down to 5.64 ng mL?1). The linear detection for protamine was in a wide range (0.1 to 1.7 μg mL?1) with the detection limit of 5.20 ng mL?1. Moreover, DSAI was successfully applied to detect heparin and protamine in complicated goat serum samples with satisfactory results. This simple and ultrasensitive biosensor has potential applications in diagnostics, therapeutics and biological research.
- Zhou, Yingxi,Jiang, Hongbo,Wang, Yuting,Zhao, Song,Hu, Lianzhe,Zhang, Yan
-
supporting information
p. 16537 - 16542
(2021/09/28)
-
- METHOD FOR THE SYNTHESIS OF 9,10-BIS(CHLOROMETHYL)ANTHRACENE
-
The invention relates to a method for the synthesis of 9,10-bis(chloromethyl)anthracene, comprising the mixing of the reagents, anthracene and 1,3,5-trioxane, a phase transfer catalyst selected from the group comprising quarternary ammonium salt and crown ether with hydrochloric acid and acetic acid.
- -
-
Paragraph 0041-0063
(2020/01/24)
-
- 2D arrays of organic qubit candidates embedded into a pillared-paddlewheel metal-organic framework
-
The creation of ordered arrays of qubits that can be interfaced from the macroscopic world is an essential challenge for the development of quantum information science (QIS) currently being explored by chemists and physicists. Recently, porous metal?organic frameworks (MOFs) have arisen as a promising solution to this challenge as they allow for atomic-level spatial control of the molecular subunits that comprise their structures. To date, no organic qubit candidates have been installed in MOFs despite their structural variability and promise for creating systems with adjustable properties. With this in mind, we report the development of a pillared-paddlewheel-type MOF structure that contains 4,7-bis(2-(4-pyridyl)-ethynyl) isoindoline N-oxide and 1,4-bis(2-(4-pyridyl)-ethynyl)-benzene pillars that connect 2D sheets of 9,10-dicarboxytriptycene struts and Zn2(CO2)4 secondary binding units. The design allows for the formation of ordered arrays of reorienting isoindoline nitroxide spin centers with variable concentrations through the use of mixed crystals containing the secondary 1,4-phenylene pillar. While solvent removal causes decomposition of the MOF, magnetometry measurements of the MOF containing only N-oxide pillars demonstrated magnetic interactions with changes in magnetic moment as a function of temperature between 150 and 5 K. Variable-temperature electron paramagnetic resonance (EPR) experiments show that the nitroxides couple to one another at distances as long as 2 nm, but act independently at distances of 10 nm or more. We also use a specially designed resonance microwave cavity to measure the face-dependent EPR spectra of the crystal, demonstrating that it has anisotropic interactions with impingent electromagnetic radiation.
- Forbes, Malcolm D. E.,Garcia-Garibay, Miguel A.,Jellen, Marcus J.,Ayodele, Mayokun J.,Cantu, Annabelle
-
supporting information
p. 18513 - 18521
(2020/11/27)
-
- AIE fluorescent probe for heparin detection and pH response, synthesis method and application
-
Relating to the field of organic luminescent materials, the invention particularly discloses an AIE fluorescent probe for heparin detection and pH response, a synthesis method and application. The fluorescent probe with AIE properties is BDA-4COOH, the fl
- -
-
Paragraph 0048-0049
(2020/04/17)
-
- Selective Binding of Dopamine and Epinephrine in Water by Molecularly Imprinted Fluorescent Receptors
-
Catecholamines play important roles in biology but their structural similarity makes it challenging to construct synthetic receptors with selective binding. A combination of covalent and noncovalent binding groups in the hydrophobic core of water-soluble
- Duan, Likun,Zhao, Yan
-
supporting information
p. 1035 - 1038
(2020/03/23)
-
- Preparation of anthracene-based tetraperimidine hexafluorophosphate and selective recognition of chromium(III) ions
-
A novel anthracene-based tetraperimidine hexafluorophosphate 3 was prepared, and its structure was determined through X-ray analysis, HRMS as well as 1H and 13C NMR spectroscopy. In the cationic moiety of 3, two (N-ethylperimidinyl–C2H4)2NCH2–arms were attached to the 9- and 10-positions of anthracene. In addition, compound 3 was used as a chemosensor to research the ability to recognize Cr3+ through fluorescence and UV titrations, HRMS, as well as 1H NMR and IR spectroscopy. The results indicate that 3 is an effective chemosensor for Cr3+
- Liu, Qing-Xiang,Yang, Feng,Zhao, Zhi-Xiang,Yu, Shao-Cong,Ding, Yue
-
p. 2847 - 2855
(2019/12/11)
-
- Plasmon-Enhanced Fluorescent Sensor based on Aggregation-Induced Emission for the Study of Protein Conformational Transformation
-
The alteration in protein conformation not only affects the performance of its biological functions, but also leads to a variety of protein-mediated diseases. Developing a sensitive strategy for protein detection and monitoring its conformation changes is of great significance for the diagnosis and treatment of protein conformation diseases. Herein, a plasmon-enhanced fluorescence (PEF) sensor is developed, based on an aggregation-induced emission (AIE) molecule to monitor conformational changes in protein, using prion protein as a model. Three anthracene derivatives with AIE characteristics are synthesized and a water-miscible sulfonate salt of 9,10-bis(2-(6-sulfonaphthalen-2-yl)vinyl)anthracene (BSNVA) is selected to construct the PEF–AIE sensor. The sensor is nearly non-emissive when it is mixed with cellular prion protein while emits fluorescence when mixed with disease-associated prion protein (PrPSc). The kinetic process of conformational conversion can be monitored through the fluorescence changes of the PEF–AIE sensor. By right of the amplified fluorescence signal, this PEF–AIE sensor can achieve a detection limit 10 pM lower than the traditional AIE probe and exhibit a good performance in human serum sample. Furthermore, molecular docking simulations suggest that BSNVA tends to dock in the β-sheet structure of PrP by hydrophobic interaction between BSNVA and the exposed hydrophobic residues.
- Cui, Yanyun,Yuan, Chang,Tan, Hongwei,Zhang, Zhanbin,Jia, Yijing,Na, Na,Ouyang, Jin
-
-
- Luminescent switching and structural transition through multiple external stimuli based on organic molecular polymorphs
-
Investigations on the relationship between multi-stimuli responsive luminescent properties and aggregation structures of polymorphs play a crucial role in developing organic multi-stimuli responsive luminescent (OMSRL) materials. Herein, we reported two p
- Shao, Bo,Jin, Rihua,Li, Aisen,Liu, Yingjie,Li, Bao,Xu, Shuping,Xu, Weiqing,Xu, Bin,Tian, Wenjing
-
supporting information
p. 3263 - 3268
(2019/03/19)
-
- Novel anthrene-based photoelectric functional materials and preparation method thereof
-
The invention discloses a novel anthracene-based photoelectric functional material and a preparation method thereof. The preparation method comprises steps as described in the specification. Accordingto the invention, the novel anthracene-based photoelectric functional material is prepared from low-priced raw materials; and the method has the advantages of few by-products, simple operation, convenient purification and high yield, and is beneficial for industrial production and cost control.
- -
-
Paragraph 0037-0046
(2019/11/29)
-
- Synthetic β-Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity
-
Reported herein is the synthesis and application of three novel β-cyclodextrin dimer hosts for the complexation of near infrared (NIR) squaraine dyes in aqueous solution. A series of eight different N-substituted N-methyl anilino squaraine dyes with variable terminal groups are investigated, with an optimal n-hexyl-substituted squaraine guest demonstrating binding constants orders of magnitude higher than the other squaraine–host combinations and comparable to literature-reported systems. Moreover, hydrophobic complexation of the squaraine dyes with the β-cyclodextrin dimer hosts causes drastic changes in the squaraine's photophysical properties, propensity for aggregation and susceptibility to hydrolytic decay.
- Chaudhuri, Sauradip,Verderame, Molly,Mako, Teresa L.,Bandara, Y. M. Nuwan D. Y.,Fernando, Ashvin I.,Levine, Mindy
-
supporting information
p. 1964 - 1974
(2018/05/15)
-
- 9,10-Bis((Z)-2-phenyl-2-(pyridin-2-yl)vinyl)anthracene: Aggregation-induced emission, mechanochromic luminescence, and reversible volatile acids-amines switching
-
Pyridine-containing luminophores have been attracting much attention due to pyridine functions in carrier transport and cation complexation. Here we prepared a butterfly-like molecule 9,10-bis(2-phenyl-2-(pyridin-2-yl)vinyl)anthracene (PyVA) for developing new multifunctional dyes. The multiple rotatable aryl groups enabled PyVA to exhibit a strong aggregation-induced emission effect, and the seriously twisted butterfly-like backbone rendered the solid weak intermolecular π-π interactions and mechanofluorochromism. Quantum chemical calculations indicated that protonation of the pyridyl units could narrow the band gap of PyVA, and X-ray crystallography revealed that PyVA molecules packed in a Z configuration in which the pyridyl units adopted a more twisted conformation with lone N-electron pairs stabilized by intra- and intermolecular CH···N and CH···π interactions. It was observed that both fluorescent crystalline and amorphous PyVA solids could sense volatile acids with a remarkably red-shifted emission, but the amorphous state was more sensitive. Moreover, the acidichromic PyVA solid could further sense volatile amines, and this alternative pH sensitive chromic process was reversible and applicable to fluorescence patterning.
- Sun, Qikun,Wang, Honghong,Xu, Xin,Lu, Yuansheng,Xue, Shanfeng,Zhang, Haichang,Yang, Wenjun
-
p. 407 - 414
(2017/10/31)
-
- Utilizing formation of dye aggregates with aggregation-induced emission characteristics for enhancement of two-photon absorption
-
Femtosecond Z-scan measurements of aggregates of a quadrupolar D-π-D dye, 9,10-bis(N-hexylcarbazol-2-yl-vinyl-2)anthracene (BHCVA), provide direct evidence that aggregation of this AIE (aggregation-induced emission) chromophore leads to a sizeable enhancement of the intrinsic two-photon absorption cross section. Aggregation-induced improvement of nonlinear response is explained by theoretical analysis of electronic structure and geometrical parameters of aggregates.
- Justyniarski, Adrian,Zar?ba, Jan K.,Hańczyc, Piotr,Fita, Piotr,Cho?uj, Marta,Zale?ny, Robert,Samo?, Marek
-
supporting information
p. 4384 - 4388
(2018/05/04)
-
- Tetraphenoquinazoline salt compound as well as preparation method and application thereof
-
The invention discloses a tetraphenoquinazoline salt compound as well as a preparation method and application thereof. The preparation method comprises the following steps: in an organic solvent, taking anthracene as a raw material and carrying out a reaction between the anthracene, paraformaldehyde, dioxane, concentrated sulfuric acid and sodium chloride to obtain 9,10-dichloromethylanthracene; then synthesizing the substance with diethanolamine to obtain 9,10-bis[bi(2'-chloroethyl) aminomethyl] anthracene; then carrying out a reaction between the substance and N-substituted benzoquinazolineto generate 9,10-bis{bi[2'-(N-ethyl benzoquinazoline)ethyl] aminomethyl} tetrabromoanthracene salt; carrying out anion exchange on the substance and NH4PF6 to obtain corresponding 9,10-bis{bi[2'-(N-ethylimidazole)ethyl]aminomethyl}anthracene hexafluorophosphate (1). The tetraphenoquinazoline salt compound disclosed by the invention has the advantages of simple preparation and obvious fluorescencephotosensitive effects, is sensitive to specific ions, can be used for producing a fluorescent molecular recognition system and an ultraviolet recognition system and is mainly applied to the technicalfield of fluorescence recognition.
- -
-
Paragraph 0016
(2018/06/04)
-
- Catalytic activities of NHC-PdCl2 species based on functionalized tetradentate imidazolium salt in three types of C-C coupling reactions
-
A functionalized tetradentate imidazolium salt 9,10-bis{di[2′-(N-ethylimidazolium-1-yl)ethyl]aminomethyl}anthracene tetrakis(hexafluorophosphate) (1) has been synthesized and characterized. The catalytic activity of the NHC-PdCl2 species formed by compound 1 and PdCl2 was tested in Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions. The results showed that this catalytic system was effective for above three types of C-C coupling reactions.
- Liu, Qing-Xiang,Zhao, Dong-Xue,Wu, Hao,Zhao, Zhi-Xiang,Lv, Shi-Zhen
-
-
- Piezochromic luminescence and aggregation induced emission of 9,10-bis[2-(2-alkoxynaphthalen-1-yl)vinyl]anthracene derivatives
-
Four derivatives of 9,10-bis[2-(2-alkoxynaphthalen-1-yl)vinyl]anthracene (BNAs) were designed, successfully synthesized and characterized by spectrofluorometer, powder wide-angle X-ray diffraction (PXRD) and differential scanning calorimetry experiments (DSC), etc. It was found that these compounds exhibited aggregation-induced emission phenomenon. Moreover, these target compounds displayed reversible color change from yellow to orange upon pressing and annealing process. Interestingly, all of BNAs obviously presented red-shifted piezofluorochromic (PFC) properties and behaved mainly length dependence of alkoxy group, in which, BNA displayed the largest PFC spectral shift (ΔlPFC?=?26?nm). The PXRD profiles demonstrated the transformation from crystalline to amorphous state upon grinding, and the mechanism of PFC behaviors was proposed. Thus, changing the length of alkoxyl chain could be an alternative way to tune their PFC behaviors.
- Teng, Xin-Yu,Wu, Xing-Chun,Cao, Yu-Qi,Jin, Yue-Hua,Li, Yang,Yan, Xi-Long,Wang, Bo-Wei,Chen, Li-Gong
-
p. 1485 - 1491
(2017/07/17)
-
- A highly sensitive and selective visible-light excitable luminescent probe for singlet oxygen based on a dinuclear ruthenium complex
-
A dinuclear Ru(ii) complex of [(bpy)2Ru(H2ipaip)Ru(bpy)2]Cl4 {bpy = 2,2′-bipyridine, H2ipaip = 2-(9-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)anthracen-10-yl)-1H-imidazo[4,5-f][1,10]phenanthroline} is newly synthesized and characterized. Singlet oxygen sensing and ground- and excited-state acid-base properties of this complex are studied. The results indicated that the complex acted as a highly sensitive and selective luminescent probe for singlet oxygen (1O2) in neutral and alkaline aqueous media under visible light excitation at 458 nm, resulting in 5.2- and 7.6-fold emission enhancement, respectively. This probe has advantages of visible light excitation, low singlet oxygen detection limits of 2.7-3.1 nM and high water solubility, thus holding great potential for applications in biological systems.
- Yin, Hong-Ju,Liu, Yan-Ju,Gao, Jie,Wang, Ke-Zhi
-
p. 3325 - 3331
(2017/03/15)
-
- Synthesis, crystal structure, Hirshfeld surface analysis, electronic structure through DFT study and fluorescence properties of a new anthracene based organic tecton
-
A new organic molecule 9,10-bis((2-(pyridin-2-yl)-1H-imidazol-1-yl)methyl)anthracene (APIM) has been synthesized. Crystal structure analysis of the molecular solid reveals that CH?π and π?π interactions are the molecular packing forces in the solid state. Thermal analysis of the molecular solid shows relatively higher decomposition temperature of the crystalline molecular solid that correlates well with the cooperative nature of CH?π and π?π interactions. Density Functional Theory (DFT) optimized structure of the molecule closely correlates with that found in the crystal. DFT optimizations also lead to the similar CH?π and π?π interaction motifs that are found within the crystal. Hirshfeld surface analysis provides detailed insight into the relative importance of various weak forces in the molecular packing. Study of the fluorescence behavior of the molecules shows quenching in the presence of metal ions.
- Pal, Nilasish,Singha, Debabrata,Jana, Atish Dipankar
-
p. 102 - 111
(2017/05/29)
-
- 9,10-Bis(N-methylcarbazol-3-yl-vinyl-2)anthracene: High contrast piezofluoro-chromism and remarkably doping-improved electroluminescence performance
-
This paper reported the synthesis, optical and electroluminescent properties of 9,10-bis(N-methylcarbazol-3-yl-vinyl-2)anthracene (MCA). MCA could be facilely prepared by the Wittig-Horner reaction of N-methyl-3-formylcarbazole and 9,10-bis(diethoxyphosphorylmethyl)anthracene and exhibited strong aggregation-induced and crystallization-enhanced emission (AIE/CEE) effect. Simple mechanical force could change MCA solid from initial green to final red emission, affording high contrast piezofluorochromism with large spectral shift of up to 90 nm. When MCA was used as the emissive material in light-emitting diodes, the doped devices showed remarkably improved electroluminescence (EL) performance whose EL efficiency was 8 times higher than that of the non-doped device. Moreover, the dopant concentrations did not affect significantly the fluorescence properties of doped films and EL performances of doped devices, demonstrating the potential advantage of AIE/CEE luminogens applicable for EL dopants.
- Liu, Wei,Ying, Shian,Sun, Qikun,Qiu, Xu,Zhang, Haichang,Xue, Shanfeng,Yang, Wenjun
-
-
- Synthesis, photophysical and electrochemical properties of a new class of fluorescent amidoanthracenophanes
-
Fluorescent amidoanthracenophanes 1, 2, 3 and 4 were obtained from the various aromatic diacid chlorides and diamino precyclophane by simple acylation. All the synthesized amidoanthracenophanes 1, 2, 3 and 4 show three intense fluorescence bands between 401 and 402, 426 and 429, and at 449 to 451 nm, and exhibit two/three oxidation reduction peaks in the cyclic voltammetry which is characteristic of fluorophoric anthracene units.
- Kannan, Ayyavoo,Rajakumar, Perumal
-
p. 73951 - 73957
(2015/09/15)
-
- Regulating the piezofluorochromism of 9,10-bis(butoxystyryl)anthracenes by isomerization of butyl groups
-
Isomers of 9,10-bis(butoxystyryl)anthracene (DSA4), including n-butyl, i-butyl and t-butyl at ortho or para positions, were designed and synthesized. All of them display an aggregation-induced emission phenomenon. Remarkably, it was found that isomerization of butyl endgroups presents significant influences on their piezofluorochromic properties. Thus, an alternative approach to design and obtain piezofluorochromic compounds is proposed here.
- Xiong, Yao,Yan, Xilong,Ma, Yawen,Li, Yang,Yin, Guohui,Chen, Ligong
-
supporting information
p. 3403 - 3406
(2015/03/04)
-
- Solvatochromism, Reversible Chromism and Self-Assembly Effects of Heteroatom-Assisted Aggregation-Induced Enhanced Emission (AIEE) Compounds
-
Two compounds, 9,10-bis[2-(quinolyl)vinyl]anthracene (BQVA) and 9,10-bis[2-(naphthalen-2-yl)vinyl]anthracene (BNVA), have been synthesised and investigated. Both of them have aggregation-induced enhanced emission (AIEE) properties. Heteroatom-assisted BQVA shows solvatochromism, reversible chromism properties and self-assembly effects. When increasing the solvent polarities, the green solution of BQVA turns to orange with a redshift of the fluorescence emission wavelengths from λ=527 to 565 nm. Notably, BQVA exhibits reversible chromism properties, including mechano- and thermochromism. The as-prepared BQVA powders show green fluorescence (λem=525 nm) and the colour can turn into orange (λem=573 nm) after grinding. Interestingly, the orange colour can return at high temperature. Based on these reversible chromism properties, a simple and convenient erasable board has been designed. Different from BQVA, non-heteroatom-assisted BNVA has no clear chromic processes. The results obtained from XRD, differential scanning calorimetry, single-crystal analysis and theoretical calculations indicate that the chromic processes depend on the heteroatoms in BQVA. Additionally, BQVA also exhibits excellent self-assembly effects in different solvents. Homogeneous nanospheres are formed in mixtures of tetrahydrofuran and water, which are then doped into silica nanoparticles and treated with 3-aminopropyltriethoxysilane to give amino-functionalised nanoparticles (BQVA-AFNPs). The BQVA-AFNPs could be used to stain protein markers in polyacrylamide gel electrophoresis.
- Niu, Caixia,You, Ying,Zhao, Liu,He, Dacheng,Na, Na,Ouyang, Jin
-
p. 13983 - 13990
(2015/09/28)
-
- NHC Tetranuclear Silver(I) Complexes and Intramolecular Extended π-π Interactions
-
A series of new acyclic tetrazolium salts featuring a central anthracence building block which were 9,10-substituted with (N-R-azoliumCH2CH2)2NCH2- groups were prepared (azolium = benzimidazolium or imidazolium, R = picolyl, ethyl, nbutyl, or benzyl). These tetrazolium salts were metalated with silver(I) leading to four novel NHC tetranuclear complexes 1-4. Molecular structures of 1-4 and one tetraimidazolium salt L1H4·(HgI4)2 were established by 1H NMR, 13C NMR spectroscopy and X-ray crystallography. Silver(I) η3-arene interactions exist in complex 1. Each molecule of complexes 2-4 contains one 42-membered and two 21-membered macrometallocycles. It was interesting to observe intramolecular extended π-π interactions originated from imidazole-anthracene-anthracene-imidazole in complexes 3 and 4. In addition, the fluorescence emission spectra of the complexes and the tetrazolium salts were studied.
- Liu, Qing-Xiang,Huo, Ran,Liu, Jun,Wei, Qing,Zhao, Xiao-Jun,Zhao, Zhi-Xiang
-
p. 3167 - 3174
(2016/01/15)
-
- Relationship between molecular stacking and optical properties of 9,10-bis((4-N,N-dialkylamino)styryl) anthracene crystals: The cooperation of excitonic and dipolar coupling
-
Five 9,10-bis((4-N,N-dialkylamino)styryl) anthracene derivatives (DSA-C1-DSA-C7) with different length alkyl chains were synthesized. They showed the same color in dilute solutions but different colors in crystals. The absorption, photoluminescence, and fluorescence decay indicate that there exist both excitonic and dipolar coupling in crystals of DSA-C1-DSA-C7. X-ray crystallographic analysis revealed that all the crystals belong to the triclinic space group P1 with one molecule per unit cell and that the molecules in every crystal have the identical orientation. This offers ideal samples to investigate the impact of the molecular stacking on the optical properties of the crystals. For the first time, the cooperation of excitonic and dipolar coupling has been comprehensively studied, and the contribution to the spectral shift from the excitonic and dipolar couplings quantitatively obtained. The experiments of amplified spontaneous emission (ASE) together with measurements of the quantum efficiency further confirmed this interpretation. The results suggest that the excitonic and dipolar couplings between the adjacent molecules are both important and jointly induce the spectral shifts of the crystals.
- Li, Feng,Gao, Na,Xu, Hai,Liu, Wei,Shang, Hui,Yang, Wenjun,Zhang, Ming
-
supporting information
p. 9991 - 9997
(2014/08/18)
-
- A turn-on fluorescent Fe3+ sensor derived from an anthracene-bearing bisdiene macrocycle and its intracellular imaging application
-
Integrating N2-hydroxyethyldiethylenetriamine with anthracene gives a [2+2] macrocycle fluorescent sensor. This sensor displays an instant/reversible turn-on response specific to Fe3+, which allows facile visualization of the Fe3+/Fe2+ transition and intracellular Fe3+ imaging. the Partner Organisations 2014.
- Qiu, Lin,Zhu, Chengcheng,Chen, Huachao,Hu, Ming,He, Weijiang,Guo, Zijian
-
supporting information
p. 4631 - 4634
(2014/05/06)
-
- Selective naked-eye detection of Hg2+ through an efficient turn-on photoinduced electron transfer fluorescent probe and its real applications
-
A simple molecular fluorescent probe 5 has been designed and synthesized by appending anthracene and benzhydryl moieties through a piperazine bridge. The probe upon interaction with different metal ions showed high selectivity and sensitivity (2 ppb) for Hg2+ through fluorescence "turn-on" response in HEPES buffer. The significant fluorescence enhancement (～10-fold) is attributable to PET arrest due to complexation with nitrogen atoms of the piperazine unit and Hg2+ in 1:2 stoichiometry, in which a naked-eye sensitive fluorescent blue color of solution changed to a blue-green (switched-on). As a proof of concept, promising prospects for application in environmental and biological sciences 5 have been utilized to detect Hg 2+ sensitively in real samples, on cellulose paper strips, in protein medium (like BSA), and intracellularly in HeLa cells. Moreover, the optical behavior of 5 upon providing different chemical inputs has been utilized to construct individual logic gates and a reusable combinational logic circuit. The combinational circuit (switch ON mode; OR logic gate) is easily resettable to the original position (switch OFF mode; INHIBIT logic gate) by applying reset chemical inputs (OH- and PO43-) with great reproducibility.
- Srivastava, Priyanka,Razi, Syed S.,Ali, Rashid,Gupta, Ramesh C.,Yadav, Suresh S.,Narayan, Gopeshwar,Misra, Arvind
-
p. 8693 - 8699
(2014/12/10)
-
- Highly strained phenylene bicyclophanes
-
Bending the rules: Strained bicyclophanes (see structure) with highly bent biphenylene units and a central aromatic moiety (yellow) forced into a perpendicular position were accessible in high yields by cyclization of the appropriate bromides by Yamamoto condensation. They were able to bind to graphite cutouts in solution and were adsorbed at the liquid/highly oriented pyrolytic graphite (HOPG) interface to form extended 2D structures. Copyright
- Ohlendorf, Gabi,Mahler, Christian W.,Jester, Stefan-S.,Schnakenburg, Gregor,Grimme, Stefan,Hoeger, Sigurd
-
supporting information
p. 12086 - 12090
(2013/12/04)
-
- Solid-state fluorescence properties and reversible piezochromic luminescence of aggregation-induced emission-active 9,10-bis[(9,9- dialkylfluorene-2-yl)vinyl]anthracenes
-
In this work, we have synthesized 9,10-bis[(9,9-dialkylfluorene-2-yl)vinyl] anthracene derivatives (FLA-Cn) with propyl, pentyl, and dodecyl side chains to investigate their fluorescence properties. The results show that FLA-Cn exhibit not only an aggregation-induced emission effect but also reversible piezofluorochromic (PFC) behaviour. Interestingly, the fluorescence emission and grinding-induced spectral shifts (ΔλPFC) of FLA-Cn solids are alkyl length-dependent: the longer alkyl-containing FLA-Cn solids show more blue-shifted emission and larger ΔλPFC. Moreover, the fluorescence emission of ground FLA-C12 solid can recover spontaneously at room temperature, Powder wide-angle X-ray diffraction and differential scanning calorimetry experiments reveal that the transformation between crystalline and amorphous states under various external stimuli is responsible for the PFC behaviour, and the spontaneous recovering emission of amorphized FLA-C12 solid is ascribed to its low cold-crystallization temperature. This work demonstrates once again the accessibility of tuning the solid-state optical properties of organic fluorophores by combining the simple alternation of molecular chemical structure and the physical change of aggregate morphology under external stimuli.
- Bu, Lingyu,Sun, Mingxiao,Zhang, Deteng,Liu, Wei,Wang, Yalong,Zheng, Meng,Xue, Shanfeng,Yang, Wenjun
-
p. 2028 - 2035
(2013/05/09)
-
- Alkoxy-position effects on piezofluorochromism and aggregation-induced emission of 9,10-bis(alkoxystyryl)anthracenes
-
Changing the linking positions of alkoxy chains can significantly alter the aggregation-induced emission and piezofluorochromic activities of 9,10-bis(alkoxystyryl)anthracenes.
- Liu, Wei,Wang, Yalong,Sun, Mingxiao,Zhang, Deteng,Zheng, Meng,Yang, Wenjun
-
supporting information
p. 6042 - 6044
(2013/07/11)
-
- Synthesis and piezochromic luminescence of aggregation-enhanced emission 9,10-bis(N-alkylcarbazol-2-yl-vinyl-2)anthracenes
-
Abstract Aggregation-enhanced emission active 9,10-bis(N-alkylcarbazol-2- yl-vinyl-2)anthracenes with changed length of N-alkyl chains (methyl, propyl, pentyl, and dodecyl) have been synthesized and their piezofluorochromic properties investigated. The results show that these homologues all exhibit remarkable piezofluorochromism with the pressing-induced spectral shifts of 36-45 nm, but the alkyl lengths do not affect significantly the fluorescence properties. The fluorescence emission changes induced by pressing can be restored by heat-annealing or solvent-fuming and regenerated by repressing. Powder wide-angle X-ray diffraction and differential scanning calorimetric experiments reveal that the transformation between crystalline and amorphous states upon external stimuli is responsible for piezofluorochromic behavior. 2013 Published by Elsevier Ltd.
- Bu, Lingyu,Li, Yiping,Wang, Jianfeng,Sun, Mingxiao,Zheng, Meng,Liu, Wei,Xue, Shanfeng,Yang, Wenjun
-
p. 833 - 838
(2013/09/12)
-
- Remarkable fluorescence change based on the protonation-deprotonation control in organic crystals
-
Insights into the origin of the fluorescence responsive to protonation-deprotonation stimuli were provided through the study on the crystals of a new stimuli-responsive molecule BP3VA. And the transformation between microcrystals demonstrated the varying emissions of the BP3VA powder. The Royal Society of Chemistry.
- Zhang, Jibo,Chen, Jinlong,Xu, Bin,Wang, Lijuan,Ma, Suqian,Dong, Yujie,Li, Bao,Ye, Ling,Tian, Wenjing
-
supporting information
p. 3878 - 3880
(2013/07/19)
-
- Multi-stimuli responsive fluorescence switching: The reversible piezochromism and protonation effect of a divinylanthracene derivative
-
A novel divinylanthracene derivative 9,10-bis((E)-2-(pyridin-4-yl)vinyl) anthracene (BP4VA) was synthesized and its two polymorphs with different crystal structures were obtained. The introduction of pyridine in BP4VA leads to multi-stimuli responsive fluorescence. An investigation of the photophysical and stimuli responsive luminescent properties of BP4VA, including the piezochromism and protonation effect, demonstrates that the piezochromic luminescence originates from changes in the molecular aggregation state. Additionally, protonation-deprotonation of the pyridine moieties in BP4VA has a significant effect on the frontier molecular orbitals, resulting in distinct green and red emissions under acid and base stimuli. This study on BP4VA provides a comprehensive insight into the mechanisms within this type of stimuli-responsive luminescent material, and suggests that BP4VA may be a potential candidate for applications in sensing, detection and display devices with remarkable color-changing properties.
- Dong, Yujie,Zhang, Jibo,Tan, Xiao,Wang, Lijuan,Chen, Jinlong,Li, Bao,Ye, Ling,Xu, Bin,Zou, Bo,Tian, Wenjing
-
p. 7554 - 7559
(2013/11/19)
-
- Piezochromic luminescence based on the molecular aggregation of 9,10-Bis((E)-2-(pyrid-2-yl)vinyl)anthracene
-
A chameleon under pressure: The observed piezochromic behavior of the title compound (BP2VA) was found to depend on its molecular aggregation state and specifically on the strength of the π-π interaction between the anthracene rings of adjacent molecules. When BP2VA is ground or placed under pressure, its molecular aggregation state changes, and a red shift in the fluorescence emission from green via orange to red occurs (see picture). Copyright
- Dong, Yujie,Xu, Bin,Zhang, Jibo,Wang, Lijuan,Chen, Jinlong,Lv, Hongguang,Wen, Shanpeng,Li, Bao,Ye, Ling,Tian, Wenjing,Tan, Xiao,Zou, Bo
-
supporting information
p. 10782 - 10785,4
(2020/09/02)
-
- Crystal structures of three host-guest complexes of methylsubstituted cucurbit[6]urils and anthracene derivatives
-
Three host-guest complexes of methylsubstituted cucurbit[6]urils host and anthracene derivatives guests were synthesized and structurally characterized by single crystal X-ray diffractions and 1H NMR technique. The hosts are dodecamethylcucurbit[6]uril (DDMeQ[6]), α,α′,δ,δ′-tetramethylcucurbit[6]uril (TMeQ[6]), and hexa-methylsubstituted cucurbituril (HSMeQ[6]) made from 3a-methyl-glycoluril. The guests are 9,10-bis[N-(aminoethylene)aminomethyl]anthracene (AN1), 9,10-bis[N-(aminopropylene) aminomethyl]anthracene (AN2) and 9,10-bis[N-(aminobutylene)aminomethyl]anthracene (AN3). The crystal structures show the compounds 1-3 with stoichiometry of {DDMeQ[6]-AN1}2+2NO3-24H2O (1), {TMeQ[6]-AN2}2+4NO3- 2H3O+10H2O (2) and {2HSMeQ[6]-AN3}2+2Cl-25H2O (3) respectively, and the formation of an exclusion or inclusion host-guest complex is dependent on the length of the substituted alkyl chains on the anthracene.
- Chen, Ze-Hua,Zhou, Fa-Geng,Zhang, Yun-Qian,Zhu, Qian-Jiang,Xue, Sai-Feng,Tao, Zhu
-
experimental part
p. 140 - 146
(2009/12/05)
-
- A rational approach to fluorescence "turn-on" sensing of α-amino-carboxylates
-
A rational approach to fluorescence turn-on sensing of amino carboxylates is described, which primarily relies on the perturbation of the quenching n-π* transition energy level of a carbonyl ionophore relative to the π-π* transition energy level of an ant
- Ryu, Dowook,Park, Eunju,Kim, Dae-Sik,Yan, Shihai,Jin, Yong Lee,Chang, Byoung-Yong,Kyo, Han Ahn
-
p. 2394 - 2395
(2008/09/18)
-
- Unexpectedly similar charge transfer rates through benzo-annulated bicyclo[2.2.2]octanes
-
A 4-(pyrrolidin-1-yl)phenyl electron donor and 10-cyanoanthracen-9-yl electron acceptor are attached via alkyne linkages to the bridgehead carbon atoms of bicyclo[2.2.2]octane and all three benzo-annulated bicyclo[2.2.2] octanes. The σ-system of bicyclo[2.2.2]octane provides a scaffold having nearly constant bridge geometry on which to append multiple, weakly interacting benzo π-bridges, so that the effect of incrementally increasing numbers of π-bridges on electron transfer rates can be studied. Surprisingly, photoinduced charge transfer rates measured by transient absorption spectroscopy in toluene show no benefit from increasing the number of bridge π-systems, suggesting dominant transport through the σ-system. Even more surprisingly, the significant changes in hybridization undergone by the σ-system as a result of benzo-annulation also appear to have no effect on the charge transfer rates. Natural Bond Orbital analysis is applied to both σ- and π-communication pathways. The transient absorption spectra obtained in 2-methyltetrahydrofuran (MTHF) show small differences between the benzo-annulated molecules that are attributed to changes in solvation. All charge transfer rates increase significantly upon cooling the MTHF solutions to their glassy state. This behavior is rationalized using combined molecular dynamics/electronic structure trajectories.
- Goldsmith, Randall H.,Vura-Weis, Josh,Scott, Amy M.,Borkar, Sachin,Sen, Ayusman,Ratner, Mark A.,Wasielewski, Michael R.
-
p. 7659 - 7669
(2008/12/22)
-
- Metal-organic frameworks (MOFs) composed of (triptycenedicarboxylato)zinc
-
Two novel 2D and 3D coordination polymers of 9,10-trip-tycenedicarboxylic acid and zinc nitrate, which form under solvothermal reaction conditions, are described. As determined by single-crystal X-ray structure analysis, their frameworks are assembled from dinuclear zinc coordination units which are interlinked by triptycenedicarboxylato (TDC) struts. In the 2D-MOF reported here, the extended network of van der Waals interactions between triptycene units as well as coordinated solvent molecules is responsible for the dense assembly of layers with a 44 net topology into the final crystal structure. The framework of the 3D-MOF is composed from [Zn2(TDC) 1.5]∞ layers with a 63 topology, the layers being interlinked by triptycenedicarboxylato pillars (bnn-net). This MOF possesses hexagonal channels which are filled with guest molecules. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Vagin, Sergei,Ott, Anna,Weiss, Hans-Christoph,Karbach, Alexander,Volkmer, Dirk,Rieger, Bernhard
-
scheme or table
p. 2601 - 2609
(2009/03/11)
-
- Perturbation of the PET process in fluorophore-spacer-receptor systems through structural modification: Transition metal induced fluorescence enhancement and selectivity
-
Several fluorescent signaling systems are built in the format fluorophore-spacer-receptor with ethylenediamine or N,N-dimethylethylenediamine as the receptor, anthracene as the fluorophore, and a methylene group as the spacer. The receptors are derivatize
- Bag, Bamaprasad,Bharadwaj, Parimal K.
-
p. 4377 - 4390
(2007/10/03)
-
- Regularities of Extra Coordination of Nitrogen-containing Ligands with an Anthracenyl-capped Zinc Porphyrin
-
3,3′-Dibutyl-4,4′-dimethylpyrrolylmethane was reacted with 9,10-bis(2-formylphenyloxymethyl)-anthracene to synthesize a capped porphyrin, and its zinc complex was prepared. The coordination properties of the capped zinc porphyrin in extra coordination wit
- Zaitseva,Zdanovich,Semeikin,Golubchikov
-
p. 467 - 472
(2007/10/03)
-
- New dimeric anthracenyl-derived Cinchona quaternary ammonium salts as phase-transfer catalysts for the asymmetric synthesis of α-amino acids
-
New dimeric cinchonidine- and cinchonine-derived ammonium salts which incorporate a dimethylanthracenyl bridge have been prepared and used as phase-transfer catalysts in the asymmetric alkylation of N-(diphenylmethylene)glycine esters in good yields and u
- Chinchilla, Rafael,Mazon, Patricia,Najera, Carmen
-
p. 927 - 931
(2007/10/03)
-
- A Synthetic Receptor Which Uses Multiple Edge-Face Interactions to Bind Aromatic Guests
-
Host 1 binds bicyclic aromatic guests such as 6-nitro-2-naphthol 2, serotonin mimic 3, and stilbene-derivative 4 with high affinity. Competition studies were performed to determine the association constants for complexation of 2-4 by 1. Lower-affinity host 14 lacked the structural requirements to form edge-face contacts with guests 2-4 and served as the competitive host. For each guest, evaluation of the geometry of the host-guest interaction by low-temperature NMR experiments revealed two edge-face interactions between the face of the anthracene bridge of 1 and the edge of the guest. The results reported in this paper suggest that the observed edge-face interactions stabilize the complexes formed by host 1. The synthesis of host 1 and the complexation of 2-4 by this host are described.
- Cloninger, Mary J.,Whitlock
-
p. 6153 - 6159
(2007/10/03)
-
- Multiple-photon chemistry of 9-(phenoxymethyl)- and 9,10-bis(phenoxymethyl)anthracenes in the laser-jet: Generation, photochemistry, and time-resolved laser-flash spectroscopy of anthracenylmethyl radicals and pulse radiolysis of 9-(bromomethyl)anthracene
-
In the high-intensity laser-jet (LJ) photolysis of 9-(phenoxymethyl)anthracene (1a) and 9,10-bis(phenoxymethyl)anthracene (1b) multiple-photon chemistry was observed. Thus, while the [4 + 4] photodimer 8a was formed as the one-photon product in the low-intensity conventional photolysis of monoether 1a, the high-intensity irradiation in the laser-jet yielded 1,2-bis(9-anthracenyl)ethane (3a), lepidopterene (4a), biplanene (5a), 9-(chloromethyl)anthracene (6a), and 9-(methoxymethyl)anthracene (7a) as main products. The product distribution depended on the solvent used: after C-O homolysis of the ether 1a, for which at least two photons are required, the resulting arylmethyl radical 2a dimerizes in benzene, in methylene chloride it engages in photoinduced electron transfer, while in methanol it undergoes photoionization. With the help of time-resolved laser-flash photolysis of the monoether 1a it was confirmed that the homolysis of the C-O bond leads to the 9-anthracenylmethyl radical 2a. The authentic radical 2a was generated independently by time-resolved pulse radiolysis and laser-flash photolysis of 9-(bromomethyl)anthracene. Analogous to the monoether 1a, the bisether 1b gave under the high intensity conditions of the laser-jet irradiation tetrabenzo[2.2]paracyclophane (3b), its photodimer (5b), 9,10-(bischloromethyl)anthracene (6b), and 9-(chloromethyl)-10-(phenoxymethyl)anthracene (9b); their distribution depended also on the solvent used. Mechanistic pathways are offered for these multiple-photon processes.
- Adam, Waldemar,Schneider, Katrin,Stapper, Marion,Steenken, Steen
-
p. 3280 - 3287
(2007/10/03)
-
- Process for preparing 9, 10-anthracenedicarboxaldehyde
-
This disclosure describes a novel process for the preparation of 9,10-anthracenedicarboxaldehyde by the oxi-dation of 9,10-bis(chloromethyl)anthracene.
- -
-
-
- Metal Ion Catalyzed Reactions of Acrylonitrile, Acrylamide, and Ethyl Acrylate by way of Their Diels-Alder Cycloadducts
-
In this paper, we report our successful efforts in coupling a cycloaddition/cycloreversion sequence to the well-documented metal ion promotion of functional group conversion in the cases of acrylonitrile to acrylamide, acrylamide to ethyl acrylate, and ethyl acrylate to acrylic acid.With 9-(2-pyridyl)anthracene as the diene, cycloadducts were prepared that underwent metal-promoted nitrile hydration, ethyl ester hydrolysis, and amide alcoholysis reactions.In addition, we report the synthesis of 9,10-bis(((2-(dimethylamino)ethyl)methylamino)methyl)anthracene, a diene capable of chelating to metal ions, as demonstrated by the successful synthesis of (9,10-bis(((2-(dimethylamino)ethyl)methylamino)methyl)anthracene-N,N',N",N)dizinc tetrachloride.
- Nanjappan, Palaniappan,Czarnik, Anthony W.
-
p. 1826 - 1833
(2007/10/02)
-
- Process for preparing 9,10-anthracenedicarboxaldehyde
-
This disclosure describes a novel process for the preparation of 9,10-anthracenedicarboxaldehyde by the oxidation of 9,10-bis(chloromethyl)anthracene.
- -
-
-
- Process for the production of 11,11,12,12-tetracyano-9,10-anthraquinodimehane _or its derivatives
-
A process for producing 11,11,12,12-tetracyano-9,10-anthraquinodimethane or its derivatives of the general formula STR1 in which Z1, Z4, Z5, and Z8 independently represent hydrogen, chlorine, hydroxy or amino group and Z2, Z3, Z6 and Z7 independently represent hydrogen, halogen, alkyl which has 1 to 8 carbon atoms, phenyl, alkylphenyl whose alkyl group has 1 to 2 carbon atoms, hyroxyalkly which has 1 to 8 carbon atoms, carboxyalkyl whose alkyl group has 1 to 8 carbon atoms, hydroxy amino, or carboxyl group, the process comprising introduction of dicyanomethyl groups into an anthracene compound of the following general formula at 9 and 10 positions STR2 in which Z1, Z2, Z3, Z4, Z5, Z6, Z7 and Z8 have the same meanings as defined above, and dehydrogenation of the dicyanomethyl groups.
- -
-
-
