Publikation:

Photochemical cis/trans isomerization of a stilbazolium betaine : a protolytic/photochemical reaction cycle

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Photochemical_cis.pdf
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1978

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Steiner, Ulrich
Abdel-Kader, Mahmoud H.
Fischer, P.
Kramer, Horst E. A.

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http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-47052
DOI (zitierfähiger Link)
https://doi.org/10.1021/ja00478a039
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Attribution-NonCommercial-NoDerivs 2.0 Generic

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Published

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Journal of the American Chemical Society. 1978, 100(10), pp. 3190-3197. ISSN 0002-7863. Available under: doi: 10.1021/ja00478a039

Zusammenfassung

Photochemical and thermal cis/trans isomerization is reported for a stilbazolium betaine (M). Obtained from synthesis in the trans configuration, M cannot be isomerized directly but only via the O-protonated form MH+trans. Photoisomerization of MH+trans yields the cis isomer MH+cis (structure established by 1H NMR) which can be deprotonated to the cis betaine. Mcis represents the first example of a cis isomer in this class of compounds. Though fairly stable in aqueous solution, Mcis can be fully reverted to the trans isomer either thermally or photochemically. The sequence Mtrans {\rightleftharpoons} MH+trans {\rightleftharpoons} MH+cis {\rightleftharpoons} Mcis → Mtrans constitutes a complete molecular reaction cycle which may serve as a chemical model for the storage of information and subsequent regeneration of the information carrier, for instance, in biological systems.

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540 Chemie

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ISO 690STEINER, Ulrich, Mahmoud H. ABDEL-KADER, P. FISCHER, Horst E. A. KRAMER, 1978. Photochemical cis/trans isomerization of a stilbazolium betaine : a protolytic/photochemical reaction cycle. In: Journal of the American Chemical Society. 1978, 100(10), pp. 3190-3197. ISSN 0002-7863. Available under: doi: 10.1021/ja00478a039
BibTex
@article{Steiner1978Photo-10005,
  year={1978},
  doi={10.1021/ja00478a039},
  title={Photochemical cis/trans isomerization of a stilbazolium betaine : a protolytic/photochemical reaction cycle},
  number={10},
  volume={100},
  issn={0002-7863},
  journal={Journal of the American Chemical Society},
  pages={3190--3197},
  author={Steiner, Ulrich and Abdel-Kader, Mahmoud H. and Fischer, P. and Kramer, Horst E. A.}
}
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