Issue 5, 2002
From the journal:

Journal of Materials Chemistry

Norman A. Bell,*a   David. J. Crouch,a   Derek J. Simmonds,a   Andres E. Goeta,b   Thomas Gelbrichc  and  Michael B. Hursthousec  

* Corresponding authors

a Department of Chemistry, Sheffield Hallam University, Howard Street, Sheffield, UK
E-mail: n.a.bell@shu.ac.uk

b Department of Chemistry, University of Durham, Durham, UK

c Department of Chemistry, University of Southampton, Southampton, UK

Abstract

The synthesis and characterization of three new solvatochromic tricyanoquinodimethane zwitterionic systems is reported. (Z)-{β-[N-(1-Propyl)benzothiazolium-2-yl]-α-cyano-4-styryl}dicyanomethanide, C3H7(2)BT3CNQ, (Z)-{β-[N-(1-propyl)benzothiazolium-2-yl]-α-cyano-4-(2,3,5,6-tetrafluorostyryl)}dicyanomethanide, C3H7(2)BT3CNQF4, and (Z)-{β-[N-(1-butyl)benzoselenazolium-2-yl]-α-cyano-4-styryl}dicyanomethanide, C4H9(2)BS3CNQ, exhibit negative solvatochromism, consistent with a transition from an ionic ground state to a significantly less polar excited state. X-Ray crystallography measurements confirm the zwitterionic ground state of these novel T3CNQ-based chromophores. The solvatochromic properties of these compounds are compared to those of a series of related quinolinium/pyridinium adducts, and also with those of the Reichardt betaine dye.

Graphical abstract: Structural and solvatochromic studies of a series of tricyanoquinodimethane-based zwitterions

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Article information

DOI
https://doi.org/10.1039/B111392P
Article type
Paper
Submitted
13 Dec 2001
Accepted
19 Feb 2002
First published
26 Mar 2002

J. Mater. Chem., 2002,12, 1274-1279

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Structural and solvatochromic studies of a series of tricyanoquinodimethane-based zwitterions

N. A. Bell, David. J. Crouch, D. J. Simmonds, A. E. Goeta, T. Gelbrich and M. B. Hursthouse, J. Mater. Chem., 2002, 12, 1274 DOI: 10.1039/B111392P

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