- 1, 3-Indanedione functionalized fluorene luminophores: Negative solvatochromism, nanostructure-morphology determined AIE and mechanoresponsive luminescence turn-on
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Luminous efficiency in polar environment and aggregated state, as well as high-contrast luminescence on/off switching under external stimuli are significant issues to be addressed in developing functional fluorescent materials. Combining the advantages of solvatochromic effect in intramolecular charge transfer (ICT) compounds with their nanostructured morphological effects, we herein report a series of A–π–D–π–A fluorene derivatives, which simultaneously exhibit negative solvatochromism, aggregation-induced emission (AIE) and mechanoresponsive luminescence (MRL) turn-on. These molecules contain the same fluorene donor (D) and 1,3-indandione acceptor (A) but differ in alkyl substituents in the 9-position of the fluorene segment, including 9,9-dibutyl (b-DIPF), 9,9-dioctyl (o-DIPF) and 9,9-didodecyl (d-DIPF). The emission colors of these compounds were changed from blue to orange-red, and the fluorescence quantum yields increased upon increasing the solvent polarity from nonpolar hexane to polar dimethyl sulfoxide. Due to the formed random nanostructured aggregates, the compounds exhibited AIE characteristics in THF/H2O mixtures. Oppositely, their emission quenched 0D particles which were afforded by quick evaporation of their dichloromethane solvents under vacuum displayed remarkable mechanoresponsive luminescence turn-on behavior. Our results suggest that rationally design ICT molecules and control their nanostructures would be promising way for realizing multifunctional fluorescent materials.
- Zhang, Fang,Zhang, Rong,Liang, Xiaozhong,Guo, Kunpeng,Han, Zhaoxiang,Lu, Xiaoqing,Xie, Jingjuan,Li, Jie,Li, Da,Tian, Xia
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- Metallacycle-cored supramolecular assemblies with tunable fluorescence including white-light emission
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Control over the fluorescence of supramolecular assemblies is crucial for the development of chemosensors and light-emitting materials. Consequently, the postsynthetic modification of supramolecular structures via host-guest interactions has emerged as an efficient strategy in recent years that allows the facile tuning of the photophysical properties without requiring a tedious chemical synthesis. Herein, we used a phenanthrene-21-crown-7 (P21C7)-based 60° diplatinum(II) acceptor 8 in the construction of three exohedral P21C7 functionalized rhomboidal metallacycles 1-3 which display orange, cyan, and green emission colors, respectively. Although these colors originate from the dipyridyl precursors 10-12, containing triphenylamine-, tetraphenylethene-, and pyrene-based fluorophores, respectively, the metal-ligand coordination strongly influences their emission properties. The metallacycles were further linked into emissive supramolecular oligomers by the addition of a fluorescent bis-ammonium linker 4 that forms complementary host-guest interactions with the pendant P21C7 units. Notably, the final ensemble derived from a 1:1 mixture of 1 and 4 displays a concentration-dependent emission. At low concentration, i.e., a blue color, whereas an orange emission was observed when the concentration exceeds >5 mM. Moreover, white-light emission was observed from the same sample at a concentration of 29 μM, representing a pathway to construct supramolecular assemblies with tunable fluorescence properties.
- Zhang, Mingming,Yin, Shouchun,Zhang, Jing,Zhou, Zhixuan,Saha, Manik Lal,Lu, Chenjie,Stanga, Peter J.
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- Synthesis of fluorene-based di-BODIPY dyes containing different aromatic linkers and their properties
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Three novel fluorene-based symmetric di-BODIPY dyes (BDPa-c) featuring a fluorene motif as the central core, BODIPY as the terminal groups, and several types of aromatic groups, including phenyl, thiophene, and furan, as linkers were synthesized. The optical and electrochemical properties of these BODIPY dyes were investigated, and DFT theoretical calculations were performed. All these dyes show absorption bands in the region of 300-650 nm with high extinction coefficients. Furan-linked dye BDPc exhibit a more coplanar molecular structure, which increases the efficient π-conjugation length and causes intensive intramolecular charge transfer (ICT), resulting in broadened and red-shifted absorption bands. The luminescence of these dyes is located in near-infrared regions with large Stokes shifts (1013-4862 cm-1). The HOMO/LUMO energy levels, as investigated by CV are approximately 5.5 eV and 3.6 eV, respectively.
- Zhao, Hongbin,Liao, Junxu,Peng, Min,Wang, Yucai,Zhou, Weinan,Li, Bohong,Shen, Songping,Xie, Zechuan
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- Conjugated polymer nanoparticles for biomedical in vivo imaging
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Conjugated polymer nanoparticles, produced by in situ colloidal Knoevenagel polymerization, show advantageous properties (bright emission, colloidal/chemical stability and mesoscopic size range) that allow the successful in vivo application to real-time sentinel lymph node mapping in a mouse model.
- Kim, Sehoon,Lim, Chang-Keun,Na, Jinhee,Lee, Yong-Deok,Kim, Kwangmeyung,Choi, Kuiwon,Leary, James F.,Kwon, Ick Chan
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- Tetrathiafulvalene Vinylogue-Fluorene Co-oligomers: Synthesis, Properties, and Supramoleclar Interactions with Carbon Nanotubes
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A series of bis(dithiafulvenyl)-end-capped fluorene derivatives was prepared and subjected to a one-pot iodine-promoted oxidative polymerization to yield π-conjugated co-oligomers containing tetrathiafulvalene vinylogue and fluorene repeat units. The resu
- Khadem, Mohammadreza,Zhao, Yuming
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- ORGANIC SEMICONDUCTING COMPOUNDS
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The invention relates to novel organic semiconducting compounds containing a polycyclic unit, to methods for their preparation and educts or intermediates used therein, to compositions, polymer blends and formulations containing them, to the use of the compounds, compositions and polymer blends as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photodetectors (OPD), organic field effect transistors (OFET) and organic light emitting diodes (OLED), and to OE, OPV, PSC, OPD, OFET and OLED devices comprising these compounds, compositions or polymer blends.
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Paragraph 0624; 0625
(2021/03/13)
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- A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and preparation method of A-pi-D-pi-A type small molecule solar cell receptor material
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The invention discloses an A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and a preparation method of the A-pi-D-pi-A type small molecule solar cell receptor material. According to the receptor material, fluorine is adopted as a central core structure, groups such as thiophene, furan and benzene are adopted as pi bridges, and aldehyde groups at both ends are subjected to a condensation reaction with active sites of an electrondrawing group thiophene indanone to obtain symmetric target molecules at normal temperature and normal pressure. The A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorine is simple in synthesis method, easy in reaction condition control, high in yield, good in universal applicability and possible in efficient synthesis, can be widely applied to fields such as energy, life, analysis, material science, and the like, and is particularly suitable for being used as organic small molecule solar cell receptor materials, and the like.
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Paragraph 0055-0056; 0059-0060
(2020/03/06)
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- NOVEL RHODAMINE-FLUORENE-RHODAMINE BASED COMPOUNDS AND CHEMOSENSOR FOR SELECTIVE DETECTION OF MERCURY IONS COMPRISING THE SAME
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The present invention relates to a novel rhodamine-fluorene-rhodamine compound and a method for detecting mercury ions using the same, wherein the rhodamine-fluorene-rhodamine compound has improved sensitivity and selectivity to harmful mercury ions present in an aqueous solution, thereby being able to detect mercury ions in a water-soluble analysis sample with high selectivity by more quickly and simply identifying colorimetric or fluorescent signals.COPYRIGHT KIPO 2020
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Paragraph 0132-0135
(2020/08/12)
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- Bridged bis-boron-dipyrromethene (BODIPY) derivative containing fluorene at meso-position and preparation method thereof
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The invention discloses a bridged double-center BODIPY derivative containing fluorene at a meso-position and a preparation method thereof. The preparation method comprises the following steps: synthesizing a symmetric dialdehyde compound containing bridging groups consisting of benzene, thiophene and furan and different substituent groups like a butyl group and an octyl group; then subjecting the symmetric dialdehyde compound and pyrrole to a reaction under the catalysis of indium trichloride so as to synthesize a bis(dipyrrolidine) compound; and successively carrying out oxidation by chloranil and fluoroboronation by boron trifluoride ether so as to obtain a fluorene-containing different bridging group-substituted BODIPY dye which has a structural general formula as shown in a formula I that is described in the specification. According to the invention, fluorene and the bridging groups consisting of benzene, thiophene and furan are introduced for the first time and conventional synthetic methods are improved, so the obtained double-center BODIPY dye has stable spectral absorption; and introduction of thiophene, furan and fluorene enables the fluorescence emission peak of the derivative presents obvious red shift, and fluorescence effect is enhanced with enhancement of system conjugative effect. The organic dye can be efficiently synthesized and widely used in fields like life science, analytical chemistry and environmental energy.
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- A supramolecular large band gap host for phosphorescent organic light-emitting diodes
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A large band gap supramolecular polymer based on host-guest interactions was developed as the host material for phosphorescent organic light-emitting diodes. The dibenzo-24-crown-8, and dibenzylammonium salt functionalized fluorene-based large band gap compounds 1 and 2 were developed as the host and guest monomers, respectively. The resulting linear supramolecular polymer (SP) 3 was obtained from the self-organization of the host and guest monomers, which was validated by nuclear magnetic resonance, viscosity and differential scanning calorimetry studies. The SP 3 maintained the triplet energy level of the host monomer 1 and the guest monomer 2. The resulting device based on the supramolecular host material and a yellow-phosphorescent complex Ir(Flpy) 3 achieved a maximum luminance efficiency of 18.2 cd A-1.
- Zhang, Jie,Zhang, Kai,Liu, Shengjian,Liang, Aihui,Huang, Xuelong,Huang, Fei,Peng, Junbiao,Cao, Yong
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p. 3829 - 3835
(2013/04/24)
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- Efficient synthesis of novel porphyrin dimers with versatile linkers via bis(dipyrromethanes) in an excellent mixed-solvent
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A general and efficient protocol has been developed to synthesise a series of novel porphyrin dimers with versatile aryl linkers via a simultaneous condensation-cyclisation-oxidation reaction of diverse bis(dipyrromethanes) with dipyrromethane-dicarbinol
- Zhao, Hongbin,Liao, Junxu,Yang, Deliang,Xie, Yujia,Xu, Yongjun,Wang, Hongke,Wang, Bangying
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p. 972 - 982
(2013/09/12)
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