This work was financially supported by a Grant-in-Aid for Scientific Research on Innovative Areas (NK) from MEXT. A.N. thanks the JSPS for a predoctral fellowship. Akinobu Matsuzawa is gratefully acknowledged for X-ray crystallographic analysis of the heterochiral aggregate of 3 b.
Reversible Heterochiral Aggregation/Dissociation of Bis(2-hydroxyphenyl)diamides Driven by UV/Vis Irradiation†
Article first published online: 19 JAN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 9, pages 2137–2141, February 27, 2012
How to Cite
Nojiri, A., Kumagai, N. and Shibasaki, M. (2012), Reversible Heterochiral Aggregation/Dissociation of Bis(2-hydroxyphenyl)diamides Driven by UV/Vis Irradiation. Angew. Chem. Int. Ed., 51: 2137–2141. doi: 10.1002/anie.201106832
- Issue published online: 22 FEB 2012
- Article first published online: 19 JAN 2012
- Manuscript Revised: 28 NOV 2011
- Manuscript Received: 26 SEP 2011
- dynamic aggregation;
- hydrogen bonds;
Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365 nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422 nm). The precipitation and dissolution is manifestly reversible.