Fluorescence spectroscopic properties of nitro-substituted diphenylpolyenes: effects of intramolecular planarization and intermolecular interactions in crystals

The Journal of Physical Chemistry. a
Yoriko SonodaMasaru Yoshida

Abstract

The steady-state absorption and fluorescence properties of (E,E,E)-1,6-diaryl-1,3,5-hexatrienes (2, aryl = 2-nitrophenyl; 3, aryl = 3-nitrophenyl; 4, aryl = 4-nitrophenyl) have been investigated in solution and in the crystalline state. The solid-state absorption spectra of 2-4 shifted to longer wavelengths than those in solution. A combination of theoretical calculations and single-crystal X-ray structure analyses shows considerable planarization of molecules in the solid state, which is mainly responsible for the spectral red shifts. The effects of intermolecular interactions on the absorption spectra appeared to be relatively small in these crystals. This is consistent with the monomeric origin of the solid-state emission. Molecule 2 was nonfluorescent in all solvents studied, probably due to the efficient nonradiative deactivation from ionic species produced by excited-state intramolecular proton transfer (ESIPT) along the C-H...O-type hydrogen bonds. The fluorescence of 3, observed only in medium polar solvents, originated from an intramolecular charge transfer (ICT*) state, while that of 4 derived from locally excited (LE*) and/or ICT* states depending on the solvent polarity. All three molecules exhibited LE* fluorescenc...Continue Reading

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Citations

Aug 10, 2011·Journal of Fluorescence·Manju Kumari SarojRamesh C Rastogi
Jul 13, 2011·The Journal of Chemical Physics·Chunmei DengBen Zhong Tang
Mar 15, 2019·Physical Chemistry Chemical Physics : PCCP·Thierry TranClémence Corminboeuf
Jun 25, 2013·Physical Chemistry Chemical Physics : PCCP·Songhua ChenYuliang Li
Aug 8, 2015·Photochemistry and Photobiology·Harsha AgnihotriSriram Kanvah
Mar 30, 2012·The Journal of Physical Chemistry. a·Qunyan WuZhigang Shuai
Jun 13, 2014·The Journal of Physical Chemistry. a·Tian ZhangZhigang Shuai
Dec 25, 2012·The Journal of Physical Chemistry. a·Yoriko SonodaMasatoshi Kanesato

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