Stimuli-responsive cyclopenta[ef]heptalenes: Synthesis and optical properties

Ebrahim H. Ghazvini Zadeh, Adam W. Woodward, David Richardson, Mykhailo V. Bondar, Kevin D. Belfield

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

We report the one-pot synthesis, 1D and 2D NMR characterization, and UV/Vis study of a series of cyclopenta[ef]heptalenes 4a-c that exhibit strong stimuli-responsive behavior, with a tunable energy gap as a result of perturbation of HOMO, LUMO, and LUMO+1 energies upon doping/dedoping with TFA/Et3N. The approach employed allows for the extension of conjugation at C-4 of the cyclopenta[ef]heptalene skeleton from X = H (4a) to X = CN (4b) and X = 2-thiophenyl (4c), resulting in longer absorption maxima and smaller optical energy gaps of the cyclopenta[ef]heptalenium cations 4a-c+. Additionally, in the presence of a UV-activated (< 300 nm) photoacid generator (PAG), protonation of 4c can be indirectly achieved by intermolecular photoinduced electron transfer (PeT) from the excited state of 4c to the PAG, upon which the latter undergoes photodecomposition resulting in the generation of acid. This phenomenon facilitates the use of cyclopenta[ef]heptalenes 4a-c as visible sensitizers of commercial PAGs.

Original languageEnglish (US)
Pages (from-to)2271-2276
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number10
DOIs
StatePublished - Apr 2015

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Azulene
  • Cyclopenta[ef]heptalene
  • Dyes/pigments
  • Electron transfer
  • Natural products
  • Photoacid generator
  • Photochromism
  • Sensitizers
  • Stimuli response

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