Journal
DYES AND PIGMENTS
Volume 90, Issue 3, Pages 284-289Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2010.12.014
Keywords
Excited-state intramolecular proton transfer (ESIPT); Ratiometric fluorescence sensor; Fluorescent nanoparticle; pH sensor; Self-assembly; Biopolymeric conjugate
Funding
- Korea Ministry of Education, Science and Technology (MEST) [2009-0081523, CRI
- RIAMIAM0209 (0417-20090011)]
- National Research Foundation of Korea [2009-0081571, 2011-0002139, 2010-00039] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A dual-emissive biopolymeric amphiphile (GC-HBO) has been prepared by densely conjugating hydrophilic glycol chitosan (GC) with a phototautomerizable hydrophobic dye (a derivative of 2-(2'-hydroxyphenyl) benzoxazole, HBO) showing excited-state intramolecular proton transfer (ESIPT). Ratiometric modulation of phototautomeric (enol-keto) dual emission, governed by the chromophoric aggregation state, was studied with a low-molecular-weight model compound (GA-HBO) and was well correlated with the nanoparticle-forming behavior of GC-HBO via amphiphilic self-assembly in water. It has been found that the promoted chromophoric aggregation at higher concentration or at basic-to-neutral pH assists the nanostructure formation to generate predominant keto emission while the enol emission is intensified at lower concentration or with decreasing pH by disintegration of self-assembled structure. The assembly-related advantageous potential of GC-HBO for probing self-concentration and surrounding pH has been demonstrated with the ratiometric determination of critical particulation concentration (0.04 kg m(-3)) and near-physiological pH sensitivity (pK(a) similar to 5.1). (C) 2011 Elsevier Ltd. All rights reserved.
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