Solvent-Dependent Nanostructures Based on Active π-Aggregation Induced Emission Enhancement of New Carbazole Derivatives of Triphenylacrylonitrile |
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Authors: | Santu Maity Dr Krishnendu Aich Chandraday Prodhan Prof Keya Chaudhuri Dr Ajoy Kumar Pramanik Prof Siddhartha Das Dr Jhuma Ganguly |
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Institution: | 1. Department of Chemistry, Indian Institute of Engineering Science and Technology, Howrah-, 711103 India;2. Molecular Genetics Department, CSIR-Indian Institute of Chemical Biology, Kolkata, 700032 India;3. Department of Chemistry, New Alipore College, University of Calcutta, Kolkata, 700053 India;4. Department of Metallurgical and Materials Engineering, Indian Institute of Technology, Kharagpur, 721302 India |
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Abstract: | In the present study, the carbazole and 2,3,3-triphenylacrylonitrile (TPAN) nanostructures (2-CTPAN and 2,2′-CTPAN) have been designed and synthesized by Pd-catalyzed Sonogashira cross-coupling reaction. CTPAN exhibit aggregation-induced emission enhancement (AIEE) behavior in water with high fluorescence quantum yield. Both the compounds show tunable self-assembly in water as well as in N,N-dimethylformamide (DMF) by extended π–π stacking interactions. CTPAN can be self-assembled into spherical particles in water and the structures of these self-assemblies have been investigated using X-ray diffraction. Interestingly, 2-CTPAN and 2,2′-CTPAN form organogels with a critical gelation concentration (CGC) of 11 and 15 mg mL?1, respectively, in DMF and exhibit acicular and rod shaped morphology, respectively. The single-crystal structure of 2-CTPAN shows that the intermolecular C?H???π interactions lock the molecular conformation into a staircase-shaped supramolecular assembly. These AIEE active compounds reveal high water dispersibility, strong yellow fluorescence with high quantum yield, promising photostability and excellent biocompatibility, which make them potential bioimaging agents. |
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Keywords: | aggregation dyes/pigments self-assembly sensors solvent effects supramolecular chemistry |
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