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Aggregation-Induced Fluorescence of Carbazole and o-Carborane Based Organic Fluorophore.

ABSTRACT: Carbazole based fluorophores 9-butyl-3,6-bis-(phenylethynyl)-9H-carbazole (1) and 9-butyl-3,6-bis-(2-phenyl-o-carborane)-9H-carbazole (2) were synthesized via Sonogashira type cross-coupling reaction and followed by insertion with decaborane. Compound 1 exhibited far more intense fluorescence than 2 in THF solution, while in solid state 2 exerted stronger fluorescence than 1. The fluorescence quenching behavior of 2 in THF solution could be attributed to the intramolecular charge transfer of donor-acceptor system in 2, which was confirmed by electrochemical experiments and DFT calculations. The fluorescence enhancement of 2 in solid state can be ascribed to aggregational induced packing which was evidenced by crystallographic study. In addition, compound 2 showed typical aggregation induced emission (AIE) behavior.

SUBMITTER: Jiao J

PROVIDER: S-EPMC6873483 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Aggregation-Induced Fluorescence of Carbazole and o-Carborane Based Organic Fluorophore.

Jiao Jiemin J Kang Jia-Xin JX Ma Yanna Y Zhao Qianyi Q Li Huizhen H Zhang Jie J Chen Xuenian X

Frontiers in chemistry 20191115

Carbazole based fluorophores 9-butyl-3,6-bis-(phenylethynyl)-9H-carbazole (1) and 9-butyl-3,6-bis-(2-phenyl-o-carborane)-9H-carbazole (2) were synthesized via Sonogashira type cross-coupling reaction and followed by insertion with decaborane. Compound 1 exhibited far more intense fluorescence than 2 in THF solution, while in solid state 2 exerted stronger fluorescence than 1. The fluorescence quenching behavior of 2 in THF solution could be attributed to the intramolecular charge t ...[more]

PMID: 31803716

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