Fluorescence switching with a photochromic auxochrome

Erhan Deniz, Salvatore Sortino, Françisco M. Raymo

Research output: Contribution to journalArticlepeer-review

53 Scopus citations


We synthesized a photoswitchable fluorescent probe incorporating a coumarin fluorophore and an oxazine photochrome within the same molecular skeleton. The visible illumination of this fluorophore-photochrome dyad results in the excitation of the fluorescent component only if the photochromic element is activated with ultraviolet irradiation. Indeed, the photoinduced opening of the oxazine ring bathochromically shifts the absorption of the coumarin fragment sufficiently to encourage its visible excitation with concomitant fluorescence. These operating principles translate into fluorescence photoactivation with good contrast ratio and brightness as well as short fluorescence lifetime. The modular character and relative simplicity of this synthetic strategy for the assembly of photoswitchable constructs might evolve into a general design logic for the photoregulation of the electronic structure of a given chromophore with a photochromic auxochrome.

Original languageEnglish (US)
Pages (from-to)3506-3509
Number of pages4
JournalJournal of Physical Chemistry Letters
Issue number24
StatePublished - Dec 16 2010

ASJC Scopus subject areas

  • Materials Science(all)
  • Physical and Theoretical Chemistry


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