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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 11
BKCSDE 26(11)
November 20, 2005 

Tailoring the Excited-State Intramolecular Proton Transfer (ESIPT) Fluorescence of 2-(2'-Hydroxyphenyl)benzoxazole Derivatives
Jangwon Seo, Sehoon Kim, Sanghyuk Park, Soo Young Park*
Excited-state intramolecular proton transfer (ESIPT), 2-(2'-Hydroxyphenyl)benzoxazole (HBO), Substituent effect, ESIPT fluorescence
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.
1706 - 1710
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