Solvatochromism of distyrylbenzene pairs bound together by [2.2]paracyclophane: Evidence for a polarizable "through-space" delocalized state

Janice W. Hong, Han Young Woo, Bin Liu, Guillermo C. Bazan

Research output: Contribution to journalArticlepeer-review

95 Citations (Scopus)


A series of compounds were designed and synthesized to examine how through-space and through-bond electron delocalization respond to solvent effects. The general strategy involves the study of "dimers" of the distyrylbenzene chromophore held in close proximity by the [2.2]paracyclophane core and a systematic dissection of the chromophore into components with through-space and through-bond electronic delocalization. Steady state and time-resolved fluorescence spectroscopy in a range of solvents reveals a red-shift in emission and an increase in the intrinsic fluorescence lifetime for the emitting state in polar solvents when donor substituents are absent. We propose that through-space delocalization across the [2.2]paracyclophane core is more polarizable in the excited state, relative to the through-bond (distyrylbenzene based) excited state. When strong donors are attached to the distyrylbenzene chromophore, the charge transfer character of the distyrylbenzene-based excited state dominates fluorescence properties.

Original languageEnglish
Pages (from-to)7435-7443
Number of pages9
JournalJournal of the American Chemical Society
Issue number20
Publication statusPublished - 2005 May 25
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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