The University of Southampton
University of Southampton Institutional Repository

Distorted electron acceptors: an unexpected reaction involving tetramethyl-TCNQ

Distorted electron acceptors: an unexpected reaction involving tetramethyl-TCNQ
Distorted electron acceptors: an unexpected reaction involving tetramethyl-TCNQ
Reactions involving the donors N-methyl-2-methylbenzothiazolium-and N-(1-propyl)-2-methylbenzothiazolium iodide with the acceptor 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-p-quinodimethane (TMTCNQ) in the presence of a suitable base lead to the isolation of novel [(Z)-beta-(N-alkylbenzothiazol-3-ium-2-yl)-alpha-cyano-2,3,5,6-tetrameth yl-4-styryl]dicyanomethanide chromophores. Under prolonged reaction periods, these first examples of charge transfer compounds incorporating the distorted TMTCNQ electron acceptor, undergo further reaction at the acrylonitrile functionality promoting the synthesis of novel thiomorpholine-based charge transfer compounds via a sulfur mediated cyclisation reaction. This second reaction illustrates a fundamentally new type of TCNQ-based chemistry as confirmed by X-ray crystallography and high-resolution mass spectrometry. A possible reaction mechanism for the formation of the thiomorpholine-based chromophores is considered.
langmuir-blodgett-films, molecules
0300-922X
1171-1174
Bell, Norman A.
6f601e84-74aa-4000-9017-b0e23dc747f0
Crouch, David J.
b026fc2c-b90b-4c63-958e-ed3dd0a6437a
High, Lawrence R.H.
c2bcccfa-7c1f-4135-9b80-f50e40cd9529
Simmonds, Derek J.
8850790b-c3cf-487f-8711-426150e45d69
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Bell, Norman A.
6f601e84-74aa-4000-9017-b0e23dc747f0
Crouch, David J.
b026fc2c-b90b-4c63-958e-ed3dd0a6437a
High, Lawrence R.H.
c2bcccfa-7c1f-4135-9b80-f50e40cd9529
Simmonds, Derek J.
8850790b-c3cf-487f-8711-426150e45d69
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Bell, Norman A., Crouch, David J., High, Lawrence R.H., Simmonds, Derek J., Coles, Simon J. and Hursthouse, Michael B. (2002) Distorted electron acceptors: an unexpected reaction involving tetramethyl-TCNQ. Journal of the Chemical Society, Perkin Transactions 1, (9), 1171-1174. (doi:10.1039/b201862b).

Record type: Article

Abstract

Reactions involving the donors N-methyl-2-methylbenzothiazolium-and N-(1-propyl)-2-methylbenzothiazolium iodide with the acceptor 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-p-quinodimethane (TMTCNQ) in the presence of a suitable base lead to the isolation of novel [(Z)-beta-(N-alkylbenzothiazol-3-ium-2-yl)-alpha-cyano-2,3,5,6-tetrameth yl-4-styryl]dicyanomethanide chromophores. Under prolonged reaction periods, these first examples of charge transfer compounds incorporating the distorted TMTCNQ electron acceptor, undergo further reaction at the acrylonitrile functionality promoting the synthesis of novel thiomorpholine-based charge transfer compounds via a sulfur mediated cyclisation reaction. This second reaction illustrates a fundamentally new type of TCNQ-based chemistry as confirmed by X-ray crystallography and high-resolution mass spectrometry. A possible reaction mechanism for the formation of the thiomorpholine-based chromophores is considered.

Full text not available from this repository.

More information

Published date: 2002
Keywords: langmuir-blodgett-films, molecules

Identifiers

Local EPrints ID: 19671
URI: http://eprints.soton.ac.uk/id/eprint/19671
ISSN: 0300-922X
PURE UUID: 9dd6516f-14e3-4dcf-8617-6502d5fc8c3c
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 16 Feb 2006
Last modified: 18 Feb 2021 16:52

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×