Synthesis and characterisation of polymerisable photochromic spiropyrans: towards photomechanical biomaterials

Colin McCoy, Louise Donnelly, David Jones, Sean Gorman

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A methodology for the synthesis of novel polymerisable spiropyrans with photomechanical properties suitable for subsequent copolymerisation with either vinyl or acrylate-based biomaterials is described. UV-vis spectroscopic characterisation of photoisomerism shows that photochromic behaviour with respect to related non-polymerisable compounds is retained and is solvent dependent. In acetone, conventional spiropyran-merocyanine photochromism is observed for nitro-spiropyran derivatives, whereas in dichloromethane both nitro-spiropyrans and spiropyrans isomerise to merocyanines which rapidly form H-aggregates. The monomers were designed such that an alkyl spacer of variable length, both electronically and sterically, separates the polymerisable moiety from the photochromic core and allows steric aspects of the resulting photomechanical behaviour to be explored. (c) 2006 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)657-661
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number4
DOIs
Publication statusPublished - 22 Jan 2007

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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