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High quantum yield both in solution and solid state based on cyclohexyl modified triphenylamine derivatives for picric acid detection

Authors :
Yuyang Zhang
Lin Kong
Jiaxiang Yang
Chenyang Zhang
Yupeng Tian
Jianting Pan
Haowei Wang
Gaobin Zhang
Source :
Dyes and Pigments. 123:257-266
Publication Year :
2015
Publisher :
Elsevier BV, 2015.

Abstract

Five triphenylamine derivatives containing cyclohexyl have been designed and synthesized with a solvent-free green procedure. The compounds possess high quantum yields both in solution and solid state. Our investigation shows that the steric effects of the chair conformation cyclohexyl and strong intramolecular hydrogen bond play a key role for the high emission. Moreover, a conjugated triphenylamine core and strong polar groups (pyridinyl and hydroxy) and their location in the molecule formed a typical non-planar push–pull electronic structure. This special chemical structure endows the molecules with solvatochromic effect and exhibit interesting fluorescent behavior in binary solvent systems of THF-H2O due to the strong intramolecular charge transfer (ICT), which has been confirmed by DFT calculation, absorption and fluorescence spectra of the compounds in different polar solvents. In addition, their high emission characters, both in solution and solid state are utilized for picric acid (PA) detection.

Details

ISSN :
01437208
Volume :
123
Database :
OpenAIRE
Journal :
Dyes and Pigments
Accession number :
edsair.doi...........a7ac5bfafc21be7249a9ea669724722b