Spreitzer, Hubert and Scholz, Markus and Gescheidt, Georg and Daub, Jörg (1996) Electron-transfer chemistry and redox-switching of stilbene-like heteroaromatic compounds - Syntheses, optoelectrochemical and ESR/ENDOR studies. LIEBIGS ANNALEN-RECUEIL, 1996 (12). pp. 2069-2077. ISSN 0947-3440
Full text not available from this repository.Abstract
Redox-active compounds, in which the electron donor and the acceptor subunits are covalently linked by a vinylene spacer group were synthesised and their properties were investigated by cyclovoltammetry, spectroelectrochemistry, and ESR/ENDOR spectroscopy. - 10-Methylphenothiazinyl, 10-methylphenoxazinyl, and phenoxathiinyl were used as electron-donating groups whereas 9,10-anthraquinon-2-yl and phenyl groups were employed as accepters. The synthesis of the push-pull-substituted stilbenes 1a, 1b, 1c, 2a, 2b, and 2c was achieved by Wittig coupling of the heterocyclic aldehydes with the anthraquinoyl or phenyl phosphonium salts. The diastereoisomers were separated either by chromatography or by crystallization. - The redox potentials of the (Z) and (E) isomers differ only slightly. Spectroelectrochemical measurements indicate that the radical cations of the phenothiazine and phenoxazine derivatives undergo rearrangement from the (Z) to the (E) isomers. On the other hand, electron attachment leads to configurationally stable radical anions. This behaviour is rationalised in terms of the electron distribution reflected by the hyperfine data established by ESR/ENDOR spectroscopy.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | OLEFIN RADICAL CATIONS; MOLECULAR ELECTRONICS; SUPRAMOLECULAR CHEMISTRY; SPIN RESONANCE; CIS-STILBENE; PHOTOISOMERIZATION; ISOMERIZATION; THALLIUM(III); PERSPECTIVES; DERIVATIVES; stilbenes; push-pull substitution; electron transfer; (Z)/(E) Isomerisation; radical ions; cyclic voltammetry; spectroelectrochemistry; ESR; ENDOR |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Prof. Dr. Jörg Daub |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 May 2023 11:38 |
| Last Modified: | 25 May 2023 11:38 |
| URI: | https://pred.uni-regensburg.de/id/eprint/51309 |
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