Solvent effects on the two-photon absorption of distyrylbenzene chromophores

Han Young Woo, Bin Liu, Bernhard Kohler, Dmitry Korystov, Alexander Mikhailovsky, Guillermo C. Bazan

Research output: Contribution to journalArticle

276 Citations (Scopus)

Abstract

A series of organic- and water-soluble distyrylbenzene-based two-photon absorption (TPA) fluorophores containing dialkylamino donor groups at the termini was designed, synthesized, and characterized. The central core was systematically substituted to modulate intramolecular charge transfer (ICT). These molecules allow an examination of solvent effects on the TPA cross section (δ) and on the TPA action cross section. In toluene, the δ values follow the order of ICT strength. The effect of solvent on δ is nonmonotonic: maximum δ was measured in an intermediate polarity solvent (THF) and was lowest in water. We failed to find a correlation between the observed solvent effect and previous theoretical predictions. Hydrogen bonding to the donor groups and aggregation of the optical units in water, which are not included in calculational analysis, may be responsible for the discrepancies between experimental results and theory.

Original languageEnglish
Pages (from-to)14721-14729
Number of pages9
JournalJournal of the American Chemical Society
Volume127
Issue number42
DOIs
Publication statusPublished - 2005 Nov 1
Externally publishedYes

ASJC Scopus subject areas

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

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