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

Structural and solvatochromic studies of a series of tricyanoquinodimethane-based zwitterions
Structural and solvatochromic studies of a series of tricyanoquinodimethane-based zwitterions
The synthesis and characterization of three new solvatochromic tricyanoquinodimethane zwitterionic systems is reported. (Z)-{?-[N-(1-Propyl)benzothiazolium-2-yl]-alpha-cyano-4-styryl}dicyanomethanide, C3H7(2)BT3CNQ, (Z)-{?-[ N-(1-propyl)benzothiazolium-2-yl]-alpha-cyano-4-(2,3,5,6-tetrafluorostyr yl)}dicyanomethanide, C3H7(2)BT3CNQF(4), and (Z)-{?-[N-(1-butyl)benzoselenazolium-2-yl]-alpha-cyano-4-styryl}dicya nomethanide, 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.
n-phenoxide betaines, x-ray-diffraction, solvent polarities, dyes
1274-1279
Bell, Norman A.
6f601e84-74aa-4000-9017-b0e23dc747f0
Crouch, David J.
b026fc2c-b90b-4c63-958e-ed3dd0a6437a
Simmonds, Derek J.
8850790b-c3cf-487f-8711-426150e45d69
Goeta, Andres E.
cc8e7803-4e0e-4a25-a2a7-30a4ed507622
Gelbrich, Thomas
42309d69-eaf1-4bb7-ba2e-db61f338e370
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Bell, Norman A.
6f601e84-74aa-4000-9017-b0e23dc747f0
Crouch, David J.
b026fc2c-b90b-4c63-958e-ed3dd0a6437a
Simmonds, Derek J.
8850790b-c3cf-487f-8711-426150e45d69
Goeta, Andres E.
cc8e7803-4e0e-4a25-a2a7-30a4ed507622
Gelbrich, Thomas
42309d69-eaf1-4bb7-ba2e-db61f338e370
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Bell, Norman A., Crouch, David J., Simmonds, Derek J., Goeta, Andres E., Gelbrich, Thomas and Hursthouse, Michael B. (2002) Structural and solvatochromic studies of a series of tricyanoquinodimethane-based zwitterions. Journal of Materials Chemistry, 12 (5), 1274-1279. (doi:10.1039/b111392p).

Record type: Article

Abstract

The synthesis and characterization of three new solvatochromic tricyanoquinodimethane zwitterionic systems is reported. (Z)-{?-[N-(1-Propyl)benzothiazolium-2-yl]-alpha-cyano-4-styryl}dicyanomethanide, C3H7(2)BT3CNQ, (Z)-{?-[ N-(1-propyl)benzothiazolium-2-yl]-alpha-cyano-4-(2,3,5,6-tetrafluorostyr yl)}dicyanomethanide, C3H7(2)BT3CNQF(4), and (Z)-{?-[N-(1-butyl)benzoselenazolium-2-yl]-alpha-cyano-4-styryl}dicya nomethanide, 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.

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More information

Published date: 2002
Keywords: n-phenoxide betaines, x-ray-diffraction, solvent polarities, dyes

Identifiers

Local EPrints ID: 19672
URI: http://eprints.soton.ac.uk/id/eprint/19672
PURE UUID: be3d6ccf-f608-4354-a0ee-2434c4ea7970

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Date deposited: 17 Feb 2006
Last modified: 15 Jul 2019 19:26

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