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  Light-induced cooperative electron–proton transfer in hydrogen-bonded networks of N,N-diaryl substituted 1,4-bisimines and meso-1,2-diaryl-1,2-ethanediols

Felderhoff, M., Smolka, T., & Sustmann, R. (1999). Light-induced cooperative electron–proton transfer in hydrogen-bonded networks of N,N-diaryl substituted 1,4-bisimines and meso-1,2-diaryl-1,2-ethanediols. Journal für praktische Chemie, 341(7), 639-648. doi:10.1002/(SICI)1521-3897(199910)341:7<639:AID-PRAC639>3.0.CO;2-P.

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 Creators:
Felderhoff, Michael1, 2, Author              
Smolka, Tanja2, Author
Sustmann, R.2, Author
Affiliations:
1Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445589              
2Essen, Institut für Organische Chemie der Universität, ou_persistent22              

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Free keywords: cooperative effects; crystal engineering; electron transfer; hydrogen bonds; photochromism
 Abstract: The 1:1 cocrystallization of 1,4-diaryl-1,4-bisimines (Ar–CHN–CH2-)2 4–11and substituted meso-1,2-diaryl-1,2-ethanediols 1–3 leads to supramolecular structures in which the diol is hydrogen bonded by one of its hydroxy groups to an imine nitrogen atom of a 1,4-bisimine. The second functionality in each molecule leads to the generation of ladderlike polymeric structures where each molecule of the diol is linked to two molecules of the 1,4-bisimine and vice versa. If the diol carries electron donor groups in the aromatic residue and the 1,4-bisimine correspondingly acceptor groups, then charge transfer interactions are observed. The excited CT complex which corresponds to a radical ion pair is stabilized by migration of a proton of a hydroxy group to the nitrogen atom of an imino group. This is supported by the appearance of a N–H vibration in the IR spectra. The reorganization is also accompanied by changes in the UV/Vis spectra and by the generation of paramagnetism in the crystalline material. The results represent a type of photochromism which has its origin in a light-induced cooperative electron–proton transfer. The photochromism is thermally reversible.

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Language(s): eng - English
 Dates: 1999-09-241999-10
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Degree: -

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Title: Journal für praktische Chemie
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 341 (7) Sequence Number: - Start / End Page: 639 - 648 Identifier: ISSN: 1436-9966
CoNE: https://pure.mpg.de/cone/journals/resource/954925572897