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, Michael; Smolka, Tanja; Sustmann, R.

doi:10.1002/(SICI)1521-3897(199910)341:7<639::AID-PRAC639>3.0.CO;2-P

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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

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Felderhoff, Michael
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Essen, Institut für Organische Chemie der Universität;

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Citation

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.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-2773-B

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.