Exploring the conformational space of bridge-substituted dithienylcyclopentenes

M. Fredersdorf, R. Göstl, A. Kolmer, V. Schmidts, P. Monecke, S. Hecht, C.M. Thiele

Research output: Contribution to journalArticleAcademicpeer-review

19 Citations (Scopus)
275 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)14545-14554
Number of pages10
JournalChemistry : A European Journal
Volume21
Issue number41
DOIs
Publication statusPublished - 1 Oct 2015

Keywords

  • conformational analysis
  • NMR spectroscopy
  • NOE
  • photochromism
  • residual dipolar couplings

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