Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 41, Pages 14545-14554Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501842
Keywords
conformational analysis; NMR spectroscopy; NOE; photochromism; residual dipolar couplings
Categories
Funding
- German Research Foundation [FOR934, SFB 658]
- European Research Council [2010-SG_257041, 2012-SG_308117]
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Stimuli responsive compounds and materials are of high interest in synthetic chemistry and materials science, with light being the most intriguing stimulus due to the possibility to remote control the physicochemical properties of a molecule or a material. There is a constant quest to design photoswitches with improved switching efficiency and especially diarylethene-type switches promise photo cyclization quantum yields up to unity. However, only limited attention has been paid towards the influence of the solution conformation on the switching efficiency. Here, we describe a detailed NMR spectroscopic investigation on the conformational distribution of bridge-substituted dithienylcyclopentenes in solution. We could discriminate between several photoactive and photoinactive as well as two diastereomorphous conformations and show that the trends observed in the switching efficiency match the conformer populations obtained from state of the art NMR parameters in solution.
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