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Solvent‐Dependent Nanostructures Based on Active π‐Aggregation Induced Emission Enhancement of New Carbazole Derivatives of Triphenylacrylonitrile
Author(s) -
Maity Santu,
Aich Krishnendu,
Prodhan Chandraday,
Chaudhuri Keya,
Pramanik Ajoy Kumar,
Das Siddhartha,
Ganguly Jhuma
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900312
Subject(s) - carbazole , aggregation induced emission , solvent , chemistry , nanostructure , solvent effects , combinatorial chemistry , photochemistry , materials science , nanotechnology , chemical engineering , organic chemistry , physics , fluorescence , engineering , quantum mechanics
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.