- Two-photon fluorescence imaging of sialylated glycans: In vivo based on a sialic acid imprinted conjugated polymer nanoprobe
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We have designed and synthesized a sialic acid (SA)-imprinted conjugated polymer nanoprobe with two-photon fluorescence properties, which exhibits specific recognition ability to the target SA and has been used for monitoring sialylated glycan levels selectively in vivo.
- Zhang, Wei,Kang, Junqing,Li, Ping,Liu, Lu,Wang, Hui,Tang, Bo
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- Optical and electronic properties of fluorene-based copolymers and their sensory applications
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A series of novel, fluorene-based conjugated copolymers, poly[(9,9-bis{propenyl}-9H-fluorene)-co-(9,9-dihexyl-9H-fluorene)] (P1), poly[(9,9-bis{carboxymethylsulfonyl-propyl}fluorenyl-2,7-diyl)-co-(9, 9-dihexyl-9H-fluorene)] (P2) and poly[(9,9-dihexylfluorene)-co-alt-(9,9-bis-(6- azidohexyl)fluorene)] (P3), are synthesized by Suzuki coupling reactions and their electrochemical properties, in the form of films, are investigated using cyclic voltammetry. The results reveal that the polymer films exhibit electrochromic properties with a pseudo-reversible redox behavior; transparent in the neutral state and dark violet in the oxidized state. Among the three polymers, P2 possesses the shortest response time and the highest coloration efficiency value. These polymers emit blue light with a band gap value of around 2.9 eV and have high fluorescent quantum yields. Their metal ion sensory abilities are also investigated by titrating them with a number of different transition metal ions; all of these polymers exhibit a higher selectivity toward Fe3+ ions than the other ions tested with Stern-Volmer constants of 4.41 × 106M-1, 3.28 × 107M -1, 1.25 × 106M-1, and 6.56 × 106M-1 for P1, P2, water soluble version of P2 (P2S) and P3, respectively.
- Ibrahimova, Vuesala,Eda Kocak, Meliha,Oenal, Ahmet M.,Tuncel, Doenues
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- Conjugated polyfluorene-based reversible fluorescent sensor for Cu(II) and cyanide ions in aqueous medium
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A blue emissive polyfluorene bearing sulfate functionality in the side chain (PFS), as a sensory polymer to selectively report the presence of Cu 2+ (detection limit down to 2.5 μM) based on the fluorescence turn-off. Surprisingly, the quenched luminescence of PFS by Cu 2+ could be turned on after the addition of CN- (detection limit down to 6 μM), making PFS a sensitive, selective, and reversible cyanide probe.
- Chakraborty, Chanchal,Singh, Pradeep,Maji, Samir K.,Malik, Sudip
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- Creating a pseudometallic state of K+ by intercalation into 18-crown-6 grafted on polyfluorene as electron injection layer for high performance PLEDs with oxygen- and moisture-stable Al cathode
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Polymer light-emitting diodes (PLEDs) suffer from inadequate lifetimes because of the use of environmentally sensitive metals as the cathodes. We present the use of water/methanol-soluble polyfluorene grafted with 18-crown-6 chelating to K+ as the electron-injection layer (EIL) for deep-blue-emission PLEDs, allowing the use of environmentally stable Al as the cathode since electron donation from the 18-crown-6 can reduce K+ to a stable "pseudometallic state", enabling it to act as an intermediate step for electron injection. Furthermore, when poly(ethylene oxide) was blended into the EIL to provide hole blocking (HB), the device exhibited the highest performance reported to date for a deep-blue-emission PLED based on a conjugated polymer as the emitting layer, with a brightness of 54-800 cd/m2 and an external quantum efficiency of 5.42%. The use of such an EI-HB layer opens a broad avenue leading toward industrialization of PLEDs.
- Lu, Hsin-Hung,Ma, Yun-Sheng,Yang, Neng-Jye,Lin, Guan-Hong,Wu, Yun-Chung,Chen, Show-An
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- Polyfluorenes with phosphonate groups in the side chains as chemosensors and electroluminescent materials
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Polyfluorenes (P1 and P2) with phosphonate groups in the side chains were designed and synthesized. Their absorption and photoluminescence spectra in solutions are solvent dependent and exhibit a red shift up to 14 and 6 nm, respectively, with increasing solvent polarity. The polymers are highly soluble in ethanol with a solution photoluminescence quantum yield of 0.74. Polymer P2 in thin film cast from ethanol shows high intrachain order as revealed by red-shifted absorption spectrum and emission spectrum along with well-resolved vibronic structure. Both P1 and P2 are highly sensitive and selective Fe 3+ sensory materials, and the sensitivity is much higher than that of model compounds 3 and 4. The highest sensitivity was observed with polymer P1, and a 210-fold fluorescence quenching in dichloromethane was achieved. Polymer light-emitting diodes (PLEDs) were also fabricated to investigate the electroluminescent properties. A luminous efficiency of 1.49 cd/A with Commission Internationale de L'Eclairage (CIE) coordinates of (0.171, 0.131) at 100 cd/m2 and a maximum brightness of 1750 cd/m2 have been demonstrated.
- Zhou, Gang,Qian, Gang,Ma, Liang,Cheng, Yanxiang,Xie, Zhiyuan,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
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- A conjugated polyelectrolyte interfacial modifier for high performance near-infrared quantum-dot photodetectors
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The photodetection properties of near-infrared quantum-dot photodetectors (NIR-QPDs) have been significantly improved by introducing novel cationic conjugated polyelectrolytes (CCPs) on ZnO. The formation of a quaternary ammonium salt at the end of the pendant groups of the CCPs generates a permanent dipole moment on the ZnO surface and effectively modifies the work function of ZnO, improving the charge transport at the interfaces between the ZnO and QD layers. The cationic charge density and the geometrical structures of CCP1-3 had crucial effects in determining the photo-responsivity (R) and detectivity (D?) of the NIR-QPDs. The higher cationic charge density of CCP2 improved the electron accepting properties of ZnO, resulting in 1.6-5.1-fold increased R values under 940 nm IR irradiation (0.1 mW cm-2,-1 V) compared to the ZnO-, ZnO/CCP1-, and ZnO/CCP3-based devices. Notably, the horizontally-aligned backbone of CCP2 toward the substrate gives a uniform film surface and insulating layer on ZnO, which improved the charge transport and maintained a relatively low and constant dark current under negative bias. As a result, D? of the CCP2-treated NIR-QPDs was increased by up to 1880% compared to the pristine ZnO-based devices, and by 200-250% compared to the CCP1- A nd CCP3-based devices.
- Jeong, Moon-Ki,Jung, In Hwan,Kang, Jinhyeon,Park, Dasom,Yim, Sanggyu
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- Synthesis and photophysical characterization of an ionic fluorene derivative for blue light-emitting electrochemical cells
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Abstract A highly fluorescent an ionic fluorene derivative 1 was synthesized and its photophysical, electrochemical and electroluminescence characteristics were investigated. Deep blue emissions were observed for compound 1 in solid as well as in dilute solutions. The synthesized compound shows high fluorescence quantum yield around 77% indicates that compound 1 can perform its role as efficient ionic emitter in LEC devices. Light-emitting electrochemical cell (LEC) devices were fabricated incorporating compound 1 without (device I) and with (device II) ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BMIM·PF6). Devices I and II exhibited blue electroluminescence maximum centered at 455 and 454 nm with CIE coordinates of (0.15, 0.21) and (0.16, 0.22), respectively. Maximum luminance and current efficiency of 1105 cd m-2 and 0.14 cd A-1 respectively, has achieved for device I while that of device II resulted in 1247 cd m-2 and 0.14 cd A-1 respectively.
- Shanmugasundaram, Kanagaraj,Subeesh, Madayanad Suresh,Sunesh, Chozhidakath Damodharan,Chitumalla, Ramesh Kumar,Jang, Joonkyung,Choe, Youngson
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- Geminal cross-coupling synthesis, ion-induced emission and lysosome imaging of cationic tetraarylethene oligoelectrolytes
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Neutral conjugated tetraarylethenes OFn (n = 1-3) and the corresponding cationic conjugated oligoelectrolytes OFn+ (n = 1-3) with aggregation-induced emission activity have been designed and synthesized using geminal cross-coupling.
- Zhou, Qi-Yuan,Xin, Bo,Wang, Ya-Long,Li, Chong,Chen, Ze-Qiang,Yu, Qi,Huang, Zhen-Li,Zhu, Ming-Qiang
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- Quenching effects of gold nanoparticles in nanocomposites formed in watersoluble conjugated polymer nanoreactors
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In this paper we describe the first example of the in situ synthesis of gold nanoparticles (AuNPs) in the presence of a water-soluble conjugated polyfluorene (NPF) presenting pendent ammonium groups, with the polymer acting as an aqueous surfactant and providing fluorescent nanoreactors. Using this approach, we produced well-dispersed NPF-AuNP nanocomposites without the need for any additional reducing agents. The photoluminescence emission intensity of NPF-AuNP nanocomposite solution was quenched to a greater extent upon increasing the concentration of AuNPs, presumably through energy transfer or electron transfer from the fluorescent polymer to the metal nanoparticles. Through variations in the degrees of protonation and deprotonation of the amino groups of NPF at different values of pH, we found that the extent of quenching of AuNPs in NPF-AuNP nanocomposite solutions was directly related to the adsorption and desorption behavior of NPF on the metal surfaces. Transmission electron microscopy revealed that the greatest aggregation of AuNPs in the nanocomposite solution occurred at pH 3, suggesting that the ammonium groups (RNMe2 at pH 8.5; RNMe2H at pH 3) of the polymer side chains adsorbed onto the AuNP surfaces under these conditions. Distinct time-resolved fluorescence signals of the AuNP-quenched NPF polymers at different values of pH confirmed the interactions between these species.
- Yang, Po-Jen,Chu, Hsuan-Chih,Lee, Yu-Hsien,Kobayashi, Takayoshi,Chen, Te-Cheng,Lin, Hong-Cheu
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- Multifunctional Probe Based on Cationic Conjugated Polymers for Nitroreductase-Related Analysis: Sensing, Hypoxia Diagnosis, and Imaging
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Nitroreductase (NTR) is overexpressed in hypoxic tumors. Moreover, hypoxia is usually considered as the most important feature of various diseases. Thus, it is important to build a sensitive and selective method for NTR detection and hypoxia diagnosis. He
- Zhang, Xiaoqian,Zhao, Qi,Li, Yanru,Duan, Xinrui,Tang, Yanli
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- Aggregation-Induced FRET via Polymer-Surfactant Complexation: A New Strategy for the Detection of Spermine
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A new water-soluble cationic conjugated polymer [9,9-bis(6′-methyl imidazolium bromide)hexyl)fluorene-co-4,7-(2,1,3-benzothiadiazole)] (PFBT-MI) was designed and synthesized via Suzuki cross-coupling polymerization in good yields without any tedious purification steps. PFBT-MI showed excellent photophysical responses toward SDS and SDBS with a detection limit of 0.12 μM/(34 ppb) and 0.13 μM/(45 ppb), respectively. Furthermore, occurrence of FRET from the donor (fluorene) to acceptor (BT units), via surfactant-induced aggregation, results in naked-eye detection of these common anionic surfactants (SDS/SDBS) as the color changes from blue to yellowish green in aqueous solution. The polymer-surfactant nanoaggregates thus formed via electrostatic as well as hydrophobic interactions have been explored for the sensitive detection of spermine (considered as an excellent biomarker for early cancer diagnosis) with a detection limit of 66 ppb (0.33 μM), which is much below the range 1-10 μM pertinent for the early diagnosis of cancer in urinary samples. This highly sensitive technique would facilitate the direct and noninvasive detection of spermine from urine rapidly and is likely to have great significance in early cancer diagnosis.
- Malik, Akhtar Hussain,Hussain, Sameer,Iyer, Parameswar Krishnan
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- Synthesis and characterization of fluorene based electron transporting materials for polymer light-emitting diodes
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We synthesized fluorene based alternating copolymers comprised of several electron withdrawing groups via Suzuki coupling polymerization. Physical properties were characterized using the UV-vis spectroscopy, photoluminescence (PL) spectroscopy. The absorption peaks of copolymers were red-shifted compared to that of corresponding fluorene homopolymer. Copyright Taylor & Francis Group, LLC.
- Ahn, Ho-Ik,Choi, Chil-Sung,Oh, Jin-Woo,Kim, Nakjoong
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- Enhanced performance in bulk heterojunction polymer solar cell using water soluble conjugated polymer
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We have synthesized water-soluble polymer, poly[(9,9-bis((6a?2-(N,N,N-trimethylammonium) hexyl)-2,7-fluorene))-alt-bisphenylfumaronitrile]dibromide (AHF-alt-PFN), the polymer typically obtained by the Suzuki type of polymerization reaction and shows good solubility in methanol. Bulk heterojunction polymer solar cells (BHJ-PSCs) fabricated by using water soluble conjugated polymer and positive (Cs+) and negative (F-, CO2-3) charge ions doping as an interfacial layer for poly(3-hexylthiophene):phenyl-C61 butyric acid methyl ester (P3HT: PCBM). We have achieved an enhancement of the short circuit density and power conversion efficiency in solar cell by introducing poly(AHF-alt-PFN) layer between the active layer and the cathode metal. The device with poly(AHF-alt-PRN) layer containing F-, CO23- showed a short circuit current density more 1.3, 2.3 times higher than those of the device without poly (AHF-alt-PFN) + ion layer. We explain the better performance in solar cell with poly (AHF-alt-PFN) + ion layer was due not only to the increase of electron mobility in poly (AHF-alt-PFN) layer but also to the decrease of the electron barrier near cathode by the addition of the negative ions.
- Park, Kyung-Yong,Lee, Jun-Sung,Namkung, Han-Sol,Koo, Min-Sik,Cho, Seong-Jin,Yoon, Byung-Woo,Kim, Young-Mo,Lee, Youn-Sik,Song, Seong-Hwan,Park, Dong-Kyu,Kim, Chung-Gi
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- Multiple functionalities of polyfluorene grafted with metal ion-intercalated crown ether as an electron transport layer for bulk-heterojunction polymer solar cells: Optical interference, hole blocking, interfacial dipole, and electron conduction
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We present a novel electron transport (ET) polymer composed of polyfluorene grafted with a K+-intercalated crown ether involving six oxygen atoms (PFCn6:K+) for bulk-heterojunction polymer solar cells (PSCs) with regioregular poly(3-hexylthiophene) (P3HT) as the donor and indene-C 60 bisadduct (ICBA) or indene-[6,6]-phenyl-C61-butyric acid methyl ester (IPCBM) as the acceptor in the active layer and with Al or Ca/Al as the cathode. A remarkable improvement in the power conversion efficiency (PCE) (measured in air) was observed upon insertion of this ET layer, which increased the PCE from 5.78 to 7.5% for a PSC with ICBA and Ca/Al (5.53 to 6.63% with IPCBM) and from 3.87 to 6.88% for a PSC with ICBA and Al (3.06 to 6.21% with IPCBM). This ET layer provides multiple functionalities: (1) it generates an optical interference effect for redistribution of light intensity as an optical spacer; (2) it blocks electron-hole recombination at the interface with the cathode; (3) it forms an interfacial dipole that promotes the vacuum level of the cathode metal; and (4) it enhances electron conduction, as evidenced by (1) the increase in total absorption of 1:1 w/w P3HT:ICBA by a factor of 1.3; (2) the reduction in the hole-only current density profile by a factor of 3.3 at 2.0 × 105 V/cm; (3) the decrease of 0.81 eV in the work function of Al from 4.28 to 3.47 eV, as determined by UV photoelectron spectroscopy; and (4) the decrease in the series resistance of PSCs with ICBA and Al by a factor of 4.5, as determined by the current-voltage characteristic under dark conditions; respectively. The PSC of 7.5% is the highest among the reported values for PSC systems with the simplest donor polymer, P3HT.
- Liao, Sih-Hao,Li, Yi-Lun,Jen, Tzu-Hao,Cheng, Yu-Shan,Chen, Show-An
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- Switchable control of hydrophilicity and hydrophobicity in conjugated polymer nanoparticles by carbon dioxide
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We synthesized yellow-emissive, fluorine-based conjugated polymer to fabricate CO2-responsive conjugated polymer nanoparticles (CPNPs). The CPNPs were functionalized with tertiary amine to have responsiveness to CO2. The amine-functi
- Kim, Hyunchul,Lee, Taek Seung
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- Synthesis and physical properties of polyfluorene derivative with imidazolium units
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A new polyfluorene derivative (PF-ImBr) with imidazole cations as side chains was synthesized to achieve a bidirectional photo-electro conversion by single-component polymer light-emitting electrochemical cell and photovoltaic cell with frozen p-i-n junction at room temperature. Various physical properties of this polymer such as UV-vis absorption and fluorescence spectra, transient absorption, fluorescence lifetime, and thermograms were studied. The optical band gap value of PF-ImBr was estimated as 2.9eV. The transient absorption spectra and fluorescence lifetime results strongly suggested no electronic interactions between fluorene chromophores in the main chain and imidazolium cations in the side chain. PF-ImBr film with a fluorescent chromophore and two cations in the repeating units can form a single component frozen p-i-n junction after being heated above 130°C.
- Heo, Hyo Jung,Nagamura, Toshihiko
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- Cucurbit[7]uril-threaded fluorene-thiophene-based conjugated polyrotaxanes
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Here we investigate the effect of cucurbit[7]uril (CB7) on the thermal and optical properties of fluorene-thiophene based conjugated polyelectrolytes. For this purpose, poly(9,9′-bis(6′′-(N,N,N-trimethylammonium)hexyl)fluorene-alt-co-thiophenelene) P1 and
- Idris,Bazzar,Guzelturk,Demir,Tuncel
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- Synthesis of polyfluorene and oligofluorene with N1-hexylcytosine side chains and their sensing ability for nucleosides
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Polyfluorene (PF) and oligofluorene (OF) with N1-hexylcytosine side chains were synthesized by Pd-complex-catalyzed condensation reactions starting from a newly synthesized monomer. The UV–vis spectra of the PF exhibit the absorption maximum at a longer wavelength than that of the OF, thus revealing that a π-conjugation system extends along the polymer chain. The PF and OF are photoluminescent in solution, and their photoluminescence (PL) intensities are gradually decreased by the addition of nucleosides such as adenosine, cytidine, and guanosine to the solution. The decrease in PL intensity is likely caused by photoinduced charge transfer (PCT) from the PF's and OF's backbones to the nucleosides, within the complexes generated by hydrogen bonding between the PF and OF cytosine group at their side chains and the nucleosides. Among the nucleosides, guanosine acted as the most effective PL quenching agent. Cyclic voltammetry (CV) analysis of the OF showed that it is electrochemically active.
- Yamaguchi, Isao,Miyawaki, Koji
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- Excimer formation by electric field induction and side chain motion assistance in polyfluorenes
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For poly(9,9-di(6-(2-(3-oxetanyl)butoxyl)hexyl)-2,7-fluorene) (POBOHF), measurements on field induction-thermally stimulated current (FI-TSC) and electroluminescence (EL) under a wide temperature range demonstrate that electric field induction (FI) accompanied by side chain motion can lead to a formation of excimers, which contribute to a growth of a green component in the EL spectrum. This phenomenon also happens to poly(9,9-di-n-octyl-2,7-fluorene) (PFO), especially under long-term operations with higher electric fields (1 × 106 V/cm), copolymers of OBOHF and FO (PF-1/1 and PF-1/3), and even cross-linked POBOHF. The higher polarity of the side chain in the polyfluorenes (PFs) can cause a more pronounced FI effect. For POBOHF, the green component can even dominate after a few cycles of device operation. Lowering the content of cross-linkable commoner in the copolymers from 50 to 25 mol % only moderately suppresses the formation of FI excimers.
- Lu, Hsin-Hung,Liu, Ching-Yang,Jen, Tzu-Hao,Liao, Jin-Long,Tseng, Hao-En,Huang, Chih-Wei,Hung, Ming-Chin,Chen, Show-An
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- Light-Harvesting Fluorescent Spherical Nucleic Acids Self-Assembled from a DNA-Grafted Conjugated Polymer for Amplified Detection of Nucleic Acids
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The ultralow concentration of nucleic acids in complex biological samples requires fluorescence probes with high specificity and sensitivity. Herein, a new kind of spherical nucleic acids (SNAs) is developed by using fluorescent π-conjugated polymers (FCPs) as a light-harvesting antenna to enhance the signal transduction of nucleic acid detection. Specifically, amphiphilic DNA-grafted FCPs are synthesized and self-assemble into FCP-SNA structures. Tuning the hydrophobicity of the graft copolymer can adjust the size and light-harvesting capability of the FCP-SNAs. We observe that more efficient signal amplification occurs in larger FCP-SNAs, as more chromophores are involved, and the energy transfer can go beyond the F?rster radius. Accordingly, the optimized FCP-SNA shows an antenna effect of up to 37-fold signal amplification and the limit of detection down to 1.7 pM in microRNA detection. Consequently, the FCP-SNA is applied to amplified in situ nucleic acid detecting and imaging at the single-cell level.
- Fang, Xiaofeng,Li, Hongyan,Lin, Li,Tian, Leilei,Wei, Zixiang,Wu, Changfeng,Xiao, Fan,Xue, Hanbing,Zhang, Wenkang,Zhao, Yan,Zhu, Yulin
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supporting information
(2022/02/10)
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- FLUORENE DERIVATIVES, POLYMERS OBTAINED FROM SAID FLUORENE DERIVATIVES AND METHOD FOR PREPARING THE SAME
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The present invention relates to a novel fluorene derivative having a structure of formula (I): wherein X is independently selected from a group consisting of Cl, Br, I, trifluoromethanesulfonate and 4-(trifluoromethyl)benzenesulfonate; Y is a group of fo
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Page/Page column 32-33
(2021/10/22)
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- An ultra-highly sensitive and selective self-enhanced AIECL sensor for public security early warning in a nuclear emergencyviaa co-reactive group poisoning mechanism
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The worldwide application of nuclear power has created the potential risk of a nuclear accident, which has been a challenge to public security. In nuclear leakages, I2radioisotopes would cause rapid, global pollution. Therefore, highly sensitive and selective I2sensors exhibit their significance in nuclear accident early warnings and treatments. Herein, a conjugated polymer was developed for I2vapor monitoring with an ultra-low limit of detection (LOD). This polymer, modified with a tertiary amine as a co-reactive group, exhibits aggregation-induced electrochemiluminescence (AIECL) and self-enhanced ECL behaviors. It is noteworthy that the tertiary amine also acts as I2vapor capturing and sensing groups to give a LOD of 0.13 ppt. Excellent selectivity was obtained in various interfering atmospheres. A new mechanism was discovered for designing vapor sensors, which is summarized as co-reactive group poisoning (CGP). To meet the high efficiency requirement of nuclear emergency monitoring, an I2sensor modified screen printed carbon electrode was used due to its low cost, lack of need for pretreatment and suitability for mass production. A matching upwardly photosensitive ECL dark box was further designed. This study reports ECL vapor monitoring for the first time and provides a novel strategy for early warning of a nuclear emergency, suggesting its significance in environmental and public security fields.
- Hua, Daoben,Liu, Peng,Pan, Jian-Bin,Wang, Ziyu,Wu, Xinqi,Xu, Jing-Juan,Xu, Meiyun,Zhang, Nan
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supporting information
p. 12584 - 12592
(2021/06/14)
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- Method for inhibiting and/or destroying biomembrane
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The invention relates to the field of biological membranes, and discloses a method for inhibiting and/or damaging a biological membrane. The method comprises the step of contacting a compound as shown in a formula (I) and a sample, wherein the sample is a sample containing the biological membrane and/or a sample capable of forming but not forming the biological membrane. By adopting the method provided by the invention, the formation of the biological membrane can be inhibited, and the mature biological membrane can be damaged. The formula (I) is shown in the description, wherein R1#, R2#, R3#, R4#, R1*, R2*, R3* and R4* are independently alkyl groups of C1 to C12; X# and X* independently express halogen; n is an integer ranging from 8 to 15; the number-average molecular weight of the compound as shown in the formula (I) ranges from 5000 to 10000.
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Paragraph 0062; 0066
(2020/03/16)
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- Star-shaped amphipathic conjugated molecular material as well as preparation method and application thereof
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The invention relates to a star-like amphiphilic conjugated molecule material, and a preparation method and application thereof. The material adopts a fluorene structure as a skeleton, pyrene as a capping group and phosphonate as a polar side group and selects different alkyl chains, and the obtained star-like amphiphilic conjugated molecule compound has a structural general formula as shown in the following formula I: (the formula I is as shown in the specification), wherein R is one of alkyl, alkoxy, alkylphenyl and alkyl phenyl with phosphate; Ar is one of benzene, triphenylamine and tri-indene. The material has the advantages of simple chemical structure, low synthesis cost and the like, has high solution processability, film-forming property and multifunctional optical-electrical characteristic, and can realize high-brightness blue light emitting and efficient cathode interface modification functions simultaneously. An organic light-emitting diode which takes the material as a light-emitting layer and an interface modification layer simultaneously can realize excellent optical-electric characteristic through a simplified device structure and solves the technical problem that high-performance multi-layer devices are processed and manufactured by the solution.
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Paragraph 0065-0069
(2020/07/23)
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- Nanoparticle releasing H2S under hypoxic condition as well as preparation method and application of nanoparticle
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The invention discloses a nanoparticle releasing H2S under a hypoxic condition as well as a preparation method and application of the nanoparticle. The nanoparticle has uniform size, good stability and good dispersity in water. The nanoparticle contains a water-soluble H2S donor, a conjugated polymer with a hypoxia response effect, an aza-BODIPY dye with a photothermal effect and a coating material coating the three materials to form the nanoparticle. The nanoparticle has uniform size and good dispersity in water, can release the H2S in the hypoxic environment and solves the problems of poor solubility, low release rate of a traditional H2S donor and the like, so that the H2S has wider application in biological diagnosis and treatment of diseases.
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Paragraph 0037-0040
(2020/09/20)
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- A water-soluble porphyrin complex preparation and application of (by machine translation)
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The present invention discloses a water-soluble porphyrin complex preparation and application, the composition is formed by porphyrin center and model oligofluorenes unit, complexes according to the invention the light intensity of the transmission and the service life of the oxygen along with the increase of the density reduction; and has higher single-wire condition oxygen quantity [...]; can be through the confocal imaging and lifetime imaging technology to detect changes in the form of front and rear cells, so as to prove it has good light power therapeutic effect. The invention of the complex in the biological imaging and photodynamic therapy has a broad application prospects. (by machine translation)
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Paragraph 0024; 0025; 0026
(2018/06/26)
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- Solubility modulation of polyfluorene emitters by thermally induced (retro)-diels-alder cross-linking of cyclopentadienyl substituents
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For cost-efficient organic electronic devices, the consecutive deposition of active layers by solution-based processes is a key benefit. We report a synthetic approach enabling solubility reduction of bis(cyclopentadienyl)- substituted polyfluorenes as emissive layers in organic light-emitting diodes (OLEDs). Thermally induced retro-Diels-Alder reaction liberates free cyclopentadiene as "protecting group" and pending cyclopentadienyl units, which crosslink the polymer strands upon cooling via [4+2] cycloadditions. The activation temperature is tuned in the range of 180-250°C through alkyl, alkoxy, or ester linkages. Ultimately, macrocyclic self-protected bis(cyclopentadienylene) moieties avoid extrusion of volatile cyclopentadiene during activation. The solvent resistance of the emissive layers after cross-linking is examined by absorption spectroscopy and white light scanning interferometry. The influence of the desolubilization procedure on the performance of solution-processed OLEDs is investigated.
- Ahrens, Lukas,Schlisske, Stefan,Strunk, Karl-Philipp,Hinkel, Felix,Melzer, Christian,Bunz, Uwe H.F.,Lemmer, Uli,Hernandez-Sosa, Gerardo,J?nsch, Daniel,Freudenberg, Jan,Müllen, Klaus
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p. 4157 - 4167
(2018/06/11)
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- An Electron Transport Layer Material and the Application Thereof
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The present invention belongs to the technical field of optoelectronic devices, and discloses an electron transport layer material and its application. This material has the following structure: wherein n is a natural number of 1 to 10000, B is a strongly polar group, A1 and A2 are the same or different aromatic ring derivatives or conjugated units containing carbon-carbon double bonds and carbon-nitrogen bonds, M is a connection unit between A2 and B and is an alkyl group containing 1 to 20 carbon atoms, or is an alkyl group in which one or more carbon atoms are replaced by one or more functional groups selected from oxygen atoms, alkenyl groups, alkynyl groups, aryl groups or ester groups, and the hydrogen atom is replaced by a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the above-mentioned functional groups.
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Paragraph 0031; 0032
(2018/02/28)
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- Modified conjugated polymer, and preparation method and application thereof
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The invention relates to the field of biomedical science, and discloses a modified conjugated polymer, and a preparation method and an application thereof. The modified conjugated polymer comprises a compound represented by formula (I) or formula (II) shown in the description; and in the formula (I) or formula (II), R1 is a group having a conjugated structure unit, R2 is a C2-C25 linear alkyl group, and R3 is a hydrophilic group. The modified conjugated polymer has the biocompatibility of phospholipid, and also has the fluorescence property of the conjugated polymer. The modified conjugated polymer is interlaced to the membrane structure of cells through the strong hydrophobic effect of the modified conjugated polymer and the natural phospholipid, so the fluorescence property of the conjugated polymer can realize the imaging of the intracellular membrane structure; and active oxygen generated under an illuminating condition can effectively oxidize adjacent unsaturated phospholipid to realize the controlled release of drugs. The modified conjugated polymer has application values in the fields of self-assembling, cell imaging, cell membrane permeability adjustment and drug controlled release.
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Paragraph 0142; 0144; 0145; 0146; 0147
(2018/01/11)
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- Widowed gathers wuwu the kind compound and its preparation method
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The invention discloses an oligofluorene compound and a preparation method thereof. The oligofluorene compound provided by the invention has a structural formula as shown in a formula II described in the specification, wherein R2 is selected from any one of the following groups: -Br, -NHBoc, -NH3Cl and -NHC=NHNH2. Oligofluorene provided by the invention has the advantages of excellent sterilization performance, high luminous efficiency, good stability, capability of being very easily regulated through a main chain or a side chain in structure and the like, thereby having an important application value.
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Paragraph 0043; 0044
(2017/10/13)
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- Oligofluorenes and its preparation method
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The invention discloses oligomeric fluorene and a preparation method thereof. The oligomeric fluorene compound provided by the invention has a structural formula represented by the formula I. R1 is any one selected from the following groups: -NHBoc, -NH3Cl, and -NHC=NHNH2. The oligomeric fluorene provided by the invention has excellent bactericidal capacity, high luminous efficiency, and good stability. The structure of oligomeric fluorene can be easily regulated through a main chain or a side chain. The oligomeric fluorene has an important application value.
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Paragraph 0039; 0040; 0041; 0042
(2017/08/25)
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- A multifunctional amphiphilic conjugated molecule material, a preparing method thereof and applications of the material
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A multifunctional amphiphilic conjugated molecule material, a preparing method thereof and applications of the material are disclosed. The material consists of fluorene and pyrene compounds efficiently emitting luminescence. Phosphonate is adopted as a polar side group. Linear molecule compounds having different alkyl chains are adopted. The general structure formula of the linear molecule compounds is shown as following, wherein R is one of C1-C30 alkyl, alkoxy, alkylphenyl, alkylphenoxy and aryl. The material has advantages of a simple chemical structure, a low synthesis cost, and the like, has good solution processing performance, film forming performance and multifunctional photoelectric characteristics, and can be adopted as a multifunctional material and achieve high-brightness blue light emission and cathode interface modification. An organic light-emitting diode adopting the material as a light emitting layer and an interface layer can achieve excellent photoelectric characteristics by adopting a simplified device structure through a solution process or an ink printing manner, thus overcoming an obstacle in conventional multi-layer device manufacturing.
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Paragraph 0048; 0049; 0051
(2017/09/28)
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- π-Conjugated polymers with pendant coumarins: Design, synthesis, characterization, and interactions with carbon nanotubes
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A series of new fluorene-based π-conjugated polymers having coumarin derivatives as part of dendritic side chains were designed and prepared using the Suzuki-Miyaura cross-coupling reaction. A new coumarin derivative bearing a heptyl side chain for solubility was utilized to ensure solubility of the final polymers. It was found that fluorescence resonance energy transfer (FRET) from the coumrains to the polyfluorene backbone was efficient, especially for the polymers decorated with lower-generation dendrons. Each of the polymers was found to interact strongly with the surface of single-walled carbon nanotubes (SWNTs) in THF, and their ability to selectively disperse specific SWNT chiralities was investigated. Photoluminescence studies revealed that the strong polymer emission is efficiently quenched in the corresponding supramolecular complexes with SWNTs. This high quenching efficiency indicates that the coumarin-polymer FRET system can be supramolecularly bound to the surface of (SWNTs to produce an energy transfer system in which the energy absorbed by the donor coumarin chromophores is channeled to the SWNTs.
- Imit, Mokhtar,Imin, Patigul,Adronov, Alex
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p. 759 - 768
(2016/10/12)
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- A New Polymer Nanoprobe Based on Chemiluminescence Resonance Energy Transfer for Ultrasensitive Imaging of Intrinsic Superoxide Anion in Mice
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Despite significant developments in optical imaging of superoxide anion (O2?-) as the preliminary reactive oxygen species, novel visualizing strategies that offer ultrahigh sensitivity are still imperative. This is mainly because int
- Li, Ping,Liu, Lu,Xiao, Haibin,Zhang, Wei,Wang, Lulin,Tang, Bo
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supporting information
p. 2893 - 2896
(2016/03/19)
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- Conjugated copolymer-photosensitizer molecular hybrids with broadband visible light absorption for efficient light-harvesting and enhanced singlet oxygen generation
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We have developed conjugated copolymer-photosensitizer molecular hybrids (PFBDBP-IPBP) with a strong, broad (from 400 nm to ～700 nm) and continuous visible absorption. The photosensitizing ability of PFBDBP-IPBP was demonstrated to be higher than that of
- He, Rongkun,Hu, Ming,Xu, Ting,Li, Chunxiang,Wu, Chuanliu,Guo, Xiangqun,Zhao, Yibing
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supporting information
p. 973 - 976
(2015/02/05)
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- Fluorene-based novel highly emissive fluorescent molecules with aggregate fluorescence change or aggregation-induced emission enhancement characteristics
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A series of luminogens containing formamide or fluorenone units, based on fluorene, have been synthesized and characterized by NMR spectroscopy, mass spectrometry and elemental analysis. Their aggregate fluorescence change and aggregation-induced emission enhancement (AIEE) characteristics were investigated by luminescence and UV/Vis spectroscopies. The results indicate that luminogens 1d and 2d, containing formamide units, exhibit significant fluorescence color changing upon aggregate formation, which is a newly observed uncommon and interesting aggregation-induced emission phenomenon. Although the luminogen 3d, with one fluorenone unit and one fluorene unit, was weakly emissive in solution, it was highly fluorescent in the aggregated state and demonstrates typical AIEE characteristics. In comparison with 3d, the luminogen 4d with one fluorenone unit and two fluorene units showed weaker AIEE behavior. In thin-films and in the solid state, luminogen 1d shows intense yellow-green emission, and other luminogens show strong yellow emitting. Among these luminogens, 4d exhibits the highest solid-state emission quantum yield.
- Chen, Zhao,Liang, Jinhua,Han, Xie,Yin, Jun,Yu, Guang-Ao,Liu, Sheng Hua
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- Selective and Sensitive Sensing of Free Bilirubin in Human Serum Using Water-Soluble Polyfluorene as Fluorescent Probe
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The adherence of serum protein on conjugated polymer is a major bottleneck in the application of the latter for selective sensing of small biomolecules in blood serum. In this report, we present new polyfluorenes with d-glucuronic acid appendage that is a nonreceptor for any serum protein, thereby providing a platform for selective sensing of free bilirubin in the clinically relevant range of 50 μmol/L in human blood serum. The appended d-glucuronic acid formed noncovalent interactions with bilirubin, which in conjunction with favorable spectral overlap between the polymers and bilirubin facilitated efficient FRET process in aqueous solutions. Addition of bilirubin resulted in the quenching of the polyfluorene emission with simultaneous appearance of bilirubin emission exhibiting visual emission color change from blue to light green. The polymer remained stable in serum even under severe basic conditions and exhibited high selectivity with visual sensitivity only toward free bilirubin in human serum in the presence of crucial interferences such as hemoglobin, proteins, biliverdin, glucose, cholesterol, and metal ions. Nanomolar sensing of bilirubin could also be demonstrated successfully using one of the d-glucuronic acid appended polymer (PF-Ph-GlcA), which could sense ～150 nm of bilirubin in human serum. The combined role of energy transfer and noncovalent interaction highlights the potential of the new polymer design for highly selective sensing activity in complex biofluids.
- Senthilkumar,Asha
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p. 3449 - 3461
(2015/06/22)
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- A polyfluorene based zwitterionic fluorescent probe for response towards biological species in aqueous media
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Water soluble zwitterionic fluorescent conjugated boronic acid-bearing polyfluorene (PFBA) has been prepared from poly(9,9′-(6″-bromohexyl) fluorene-co-alt-1,4-phenylene) (polymer 3) through a post-polymerized quaternization with 3-pyridineboronic acid. Titration of diol containing monosaccharides (d-glucose and d-fructose), l-ascorbic acid and l-DOPA with PFBA polymer in 0.1 M phosphate buffer (pH 7.4) solution results in significant concentration dependent quenching of the blue fluorescence of the polymer due to static quenching as the bio-analytes form a ground state boronate ester complex with PFBA. Upon addition of d-glucose, the emission colour of PFBA changes to greenish-yellow owing to the effective induced aggregated polymer structure. PFBA also exhibits maximum response to the biological analytes at pH 7.4 which provides a scope for PFBA to be used in biological systems.
- Chakraborty, Chanchal,Bera, Manas Kumar,Malik, Sudip
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p. 3522 - 3528
(2014/08/05)
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- A novel fluorene-based gold(i) complex with aggregate fluorescence change: A single-component white light-emitting luminophor
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A new fluorene-based white light-emitting gold(i) complex with aggregate fluorescence change is reported. The novel luminogen emits direct white light in the solid state without involving complex doping/mixing procedures. This journal is the Partner Organisations 2014.
- Chen, Zhao,Wu, Di,Han, Xie,Liang, Jinhua,Yin, Jun,Yu, Guang-Ao,Liu, Sheng Hua
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supporting information
p. 11033 - 11035
(2014/11/08)
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- Varying anionic functional group density in sulfonate-functionalized polyfluorenes by a one-phase Suzuki polycondensation
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A series of anionically functionalized polyfluorene-based conjugated polyelectrolytes were synthesized by the Suzuki polycondensation of the boronic ester 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di(1-(2-(2- methoxyethoxy)ethoxy)ethyl)fluorene with the ionic and nonionic dihalides 2,7-dibromo-9,9-di(6-sodium sulfonate-hexyl)fluorene and 2,7-dibromo-9,9-di(1- (2-(2-methoxyethoxy)ethoxy)ethyl)fluorene. The latter monomer served as a diluent to control the ionic functional group density. The use of the triethylene glycol monomethyl ether derivatives made possible a one-phase polycondensation in a THF/methanol/Na2CO3(aq) mixture using Pd(PPh3)4. The one-phase nature of the polymerization was essential to balancing the reactivity of the dihalides so that they were both incorporated into the same polymer and so that the polymer composition became dictated by the monomer feedstock composition. In closely related two-phase reactions, a mixture of polymers, one ionic and one nonionic, was isolated with no control over ionic functional group density possible. Using the one-phase approach, polyfluorene-based polyelectrolytes were synthesized with 2-20 aromatic rings per sulfonate group.
- Stay, David,Lonergan, Mark C.
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p. 4361 - 4369
(2013/07/27)
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- High-efficiency polymer solar cells via the incorporation of an amino-functionalized conjugated metallopolymer as a cathode interlayer
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An amino-functionalized conjugated metallopolymer PFEN-Hg was developed as a cathode interlayer for inverted polymer solar cells. The resulting devices exhibited significantly improved performance with power conversion efficiencies exceeding 9%. Moreover, good device performance was achievable with the PFEN-Hg over a wider range of film thickness, likely due to the Hg-Hg interactions and improved π-π stacking.
- Liu, Shengjian,Zhang, Kai,Lu, Junming,Zhang, Jie,Yip, Hin-Lap,Huang, Fei,Cao, Yong
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supporting information
p. 15326 - 15329
(2013/11/06)
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- Selective detection of cyanide by a polyfluorene-based organoboron fluorescent chemodosimeter
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Organoboron-based polymeric fluorescent probes have been designed and synthesized for the sensitive and selective detection of toxic cyanide ions by a fluorescence turn off mechanism. Bis-(bromohexyl)-polyfluorenes have been synthesized by Pd catalyzed Suzuki cross-coupling polymerization. Its treatment with (Mes)2BF achieved organoboron-appended polyfluorene (PFBP). PFBP that is soluble in common organic solvents shows bright blue luminescence under UV-irradiation. The substantial quenching of the luminescence of a PFBP solution in the presence of toxic cyanide ions (CN-) has been observed. This is due to the formation of strong covalent bonds between the cyanide ions and trivalent boron centres of the side chains of the PFBP, which is further supported by NMR studies. The polyfluorene backbone of the PFBP acts as the fluorophore, and the boron centre as the cyanide acceptor. This novel type of polymeric material will find a potential application in sensor technology, as the detection limit is very low at ～0.5 μM.
- Chakraborty, Chanchal,Bera, Manas Kumar,Samanta, Partha,Malik, Sudip
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p. 3222 - 3228
(2013/10/01)
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- A Diels-Alder crosslinkable host polymer for improved PLED performance: The impact on solution processed doped device and multilayer device performance
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We report on the synthesis of a polyfluorene derivative, PFO(X), with furan pendant groups capable of Diels-Alder crosslinking with a maleimide containing small molecule passive crosslinker (PC) and a maleimide containing red emitting donor-acceptor-donor dopant molecule, bE-BTD(X). It was initially intended that a blend of these three components would afford a system where the dopant concentration could be increased to the point where complete energy transfer from the host polymer to the emissive dopant would be achieved. Because such systems often suffer from quenching and shifts in emission maxima indicative of emitter aggregation, it was hypothesized that crosslinking the emissive dopant with the host polymer would lead to de-aggregation of the dopant emitter. In thin films of PFO(X) and bE-BTD(X), a 16 nm bathochromic shift is observed in the emission maximum when the dopant concentration is increased from 1% to 8%, suggesting that the dopant is aggregating. In similar films where PC is included and the film is heated to affect crosslinking, a comparable 16 nm shift in the emission maximum is observed indicating that aggregation is still occurring and not affected by the heating step. Similar decreases in luminance are observed independent of whether the heating step is included. Not unexpectedly, however, crosslinking does afford an insoluble network that allows for the subsequent solution deposition of additional layers. When an electron transport layer (ETL) is used in PFO(X)/PC devices, increases of 190% and 490% are observed in luminance and luminous efficiency, respectively, relative to devices without an ETL indicating that this Diels-Alder crosslinkable system is amenable to multilayer deposition by solution methods. When bE-BTD(X) is included as the dopant emitter, similar increases in luminance and luminous efficiency are observed with the ETL included compared to devices where this layer is omitted.
- Patel, Dinesh G.,Graham, Kenneth R.,Reynolds, John R.
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supporting information; experimental part
p. 3004 - 3014
(2012/05/20)
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- A soluble and conductive polyfluorene ionomer with pendant imidazolium groups for alkaline fuel cell applications
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Solvent processable polyfluorene ionomers with pendant imidazolium groups were synthesized and characterized. The synthesized polymeric membranes are transparent, flexible, and mechanically strong and exhibit hydroxide ion conductivity above 10-2/su
- Lin, Bencai,Qiu, Lihua,Qiu, Bo,Peng, Yu,Yan, Feng
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experimental part
p. 9642 - 9649
(2012/03/22)
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- Facile photopatterning of polyfluorene for patterned neuronal networks
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In this paper, we demonstrated a facile photopatterning method that uses photocrosslinkable polyfluorene to fabricate micro-sized photopatterns on transparent indium tin oxide substrate for neuronal patterning. The modified poly(ethyleneimine) (m-PEI) with trimethoxysilane moiety was chemically attached to the hydroxyl group-terminated ITO surface and then the photopatternable polyfluorene derivative was spin coated as a cell-repellent layer onto the m-PEI-coated surface. The well-defined micropatterns were easily created over an entire surface by photocrosslinking of bromoalkyl-substituted polyfluorene (Br-PF) via the radical coupling reaction of a C-Br bond under UV irradiation without an initiator. UV-Vis absorbance, photoluminescence, ATR-FTIR and X-ray photoelectron spectroscopy were used to confirm the photocrosslinking process and the surface composition before and after the photocrosslinking of polyfluorene. The pairing of adhesive m-PEI and repulsive Br-PF effectively guided the neurite outgrowth and controlled neurite extension from individual neurons to the pre-patterned direction with excellent pattern fidelity. Guided neuronal cells were maintained for at least 25 days in vitro without any detachment of neuronal cells during cell culture. A photopatternable polyfluorene derivative in combination with cell-adhesive m-PEI is proved to be an effective way to modify the electrode surface to achieve single cell level neuronal networks.
- Baek, Nam Seob,Kim, Yong Hee,Han, Young Hwan,Lee, Bong Joon,Kim, Tae-Dong,Kim, Sin-Tae,Choi, Young-Seok,Kim, Gook Hwa,Chung, Myung-Ae,Jung, Sang-Don
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experimental part
p. 10025 - 10031
(2012/05/20)
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- WATER-SOLUBLE SILSESQUIOXANES AS ORGANIC QUANTUM DOTS FOR SENSING AND IMAGING
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This invention includes a compound represented by the following structural formula (I) or an acceptable salt thereof.
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Page/Page column 19
(2011/04/25)
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- Synthesis and characterization of amino-functional, blue light-emitting copolymers and their composites with CdTe nanocrystals
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Random side-chain functionalized copolymers were synthesized, utilizing a facile Yamamoto protocol by applying 2,7-dibromo-9,9-bis(6-bromohexyl)-9H-fluorene, (E)-1,2-bis(4-bromophenyl)ethene, 2,7-dibromo-9,9-dioctyl-9H-fluorene as comonomers. The precurso
- Kanelidis, Ioannis,Elsner, Victoria,B?tzer, Monique,Butz, Maren,Lesnyak, Vladimir,Eychmüller, Alexander,Holder, Elisabeth
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scheme or table
p. 5669 - 5673
(2011/11/29)
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- Exploiting an imidazole-functionalized polyfluorene derivative as a chemosensory material
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The synthesis and characterization of an alternating polyfluorene copolymer with imidazole ligand as the receptor in the pendent side chains were investigated. This system took the advantage of the effective π-conjugation and strong luminescence properties of the polyfluorene. Highly effective transitional metal-sensitive chemosensors were developed through metal ion-coordinating ability of imidazoles and strong luminescence of polyfluorenes. The results show that polymers containing imidazole groups act as promising active materials for application as fluorescent chemosensors.
- Zhou, Xing-Hua,Yan, Ji-Chao,Pei, Jian
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p. 7078 - 7080
(2007/10/03)
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