Tailoring the excited-state intramolecular proton transfer (ESIPT) fluorescence of 2-(2′-hydroxyphenyl)benzoxazole derivatives

Jangwon Seo, Sehoon Kim, Sanghyuk Park, Young Park Soo

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The excited-state intramolecular proton transfer (ESIPT) fluorescence in the 2-(2′-hydroxyphenyl)benzoxazole (HBO) derivatives with different electron donor and acceptor substituents was studied by spectroscopic and theoretical methods. Changes in the electronic transition, energy levels, and orbital diagrams of HBO analogues were investigated by the semi-empirical molecular orbital calculation and were correlated with the experimental spectral position of ESIPT keto emission. It was found that the presence of substituents, regardless of their nature, resulted in the red-shifted absorption relative to HBO. However, the spectral change of the ESIPT fluorescence was differently affected by the nature of substituent: hypsochromic shift with electron donor and bathochromic shift with electron acceptor.

Original languageEnglish
Pages (from-to)1706-1710
Number of pages5
JournalBulletin of the Korean Chemical Society
Issue number11
Publication statusPublished - 2005 Nov 20
Externally publishedYes



  • 2-(2′- Hydroxyphenyl)benzoxazole (HBO)
  • ESIPT fluorescence
  • Excited-state intramolecular proton transfer (ESIPT)
  • Substituent effect

ASJC Scopus subject areas

  • Chemistry(all)

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