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alpha,omega-diphenylpolyenes cabable of exhibiting twisted intramolecular charge transfer fluorescence: A fluorescence and fluorescence probe study of nitro- and nitrocyano-substituted 1,4-diphenylbutadienes

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Title alpha,omega-diphenylpolyenes cabable of exhibiting twisted intramolecular charge transfer fluorescence: A fluorescence and fluorescence probe study of nitro- and nitrocyano-substituted 1,4-diphenylbutadienes
 
Creator SINGH, AK
DARSHI, M
KANVAH, S
 
Subject pull diphenyl-polyenes
excited-state
photoisomerization
photophysics
photochemistry
spectroscopy
stilbenes
tict
polarization
recognition
 
Description 1,4-Diphenylbutadiene compounds, namely 1-p-cyanophenyl-4-phenylbuta-1E,3E-diene (2), 1-p-nitrophenyl-4-phenylbuta-1E,3E-diene (3), 1-cyano-1,4-diphenylbuta-1Z,3E-diene (4), 1-p-cyanophenyl-4-p-nitrophenylbuta-1E,3E-diene (5), 1-cyano-1-p-nitrophenyl-4-phenylbuta-1Z,3E-diene (6), and 1-cyano-1-phenyl-4-p-nitrophenylbuta-1Z,3E-diene (7), have been synthesized and their absorption and fluorescence properties in organic solvents, water-dioxane, and SDS, CTAB, and Triton-X-100 micelles have been investigated. The fluorescence behavior of these dienes has also been examined in ethanol-methanol (1:1) matrix at 298 and 77 K. The dienes with nitro substituents on the aromatic ring are capable of exhibiting dramatically redshifted fluorescence emission due to twisted intramolecular charge-transfer excited states. The fluorescence properties of nitro-substituted dienes 3, and 5-7 have been utilized to probe the microenvironment of SDS and CTAB micelles Ln terms of dielectric constant of water-micelle interface, location of the probe molecules in the micelles, and the cme values. This study has brought out interesting features of the excited state structure and potential energy surface of diphenylpolyenes. It further provides new directions for the development of fluorescence probes as sensors and reporters of microenvironments of organized assemblies.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-13T15:47:26Z
2011-12-26T12:47:56Z
2011-12-27T05:42:26Z
2011-07-13T15:47:26Z
2011-12-26T12:47:56Z
2011-12-27T05:42:26Z
2000
 
Type Article
 
Identifier JOURNAL OF PHYSICAL CHEMISTRY A, 104(3), 464-471
1089-5639
http://dx.doi.org/10.1021/jp992275a
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3711
http://hdl.handle.net/10054/3711
 
Language en