Distorted electron acceptors: an unexpected reaction involving tetramethyl-TCNQ
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)
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Official URL: http://dx.doi.org/10.1039/b201862b
Description/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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | langmuir-blodgett-films, molecules |
| Related URLs: | http://dx.doi.org/10.1039/b201862b |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 19671 |
| URI: | http://eprints.soton.ac.uk/id/eprint/19671 |
| Deposited On: | 16 Feb 2006 |
| Last Modified: | 01 Jun 2011 07:13 |
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