A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties

Heping Shi*, Jinwei Yang, Xiuqing Dong, Li Fang, Chuan Dong, Martin M F CHOI

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A novel asymmetric acceptor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-dimesitylboryl-5,11-dihexylindolo[3,2-b]carbazole (BDDICZ), has been successfully synthesized by introducing a benzothiazole (electron-acceptor) moiety and a dimesitylboron (electron-acceptor) group to 2-position and 8-position of indolo[3,2-b]carbazole (an electron-donor), respectively. The structure of BDDICZ was fully characterized by NMR, MS and elemental analysis and was studied by both experimental and theoretical methods. Our results demonstrate that BDDICZ is a sensitive ratiometric fluorescence probe which shows remarkable color change with fluoride ion (F-). The theoretical calculations confirm that BDDICZ can readily react with tetrabutylammonium fluoride (Bu4N+F-) to form an adduct of (Bu4N)+(BDDICZ·F)-. Moreover, BDDICZ possesses appropriate HOMO and LUMO energy states and a high fluorescence quantum yield, indicating its potential application as an ideal hole-transporting and/or light-emitting material in optoelectronic devices.

Original languageEnglish
Pages (from-to)42-48
Number of pages7
JournalSynthetic Metals
Volume179
DOIs
Publication statusPublished - 2013

Scopus Subject Areas

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Mechanics of Materials
  • Mechanical Engineering
  • Metals and Alloys
  • Materials Chemistry

User-Defined Keywords

  • Benzothiazole
  • Dimesitylboron
  • Donor-π-acceptor
  • Indolo[3,2-b]carbazole
  • Photophysical properties
  • Sensing properties

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