Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile

Chang Keun Lim; Jangwon Seo; Sehoon Kim; Ick Chan Kwon; Cheol Hee Ahn; Soo Young Park

doi:10.1016/j.dyepig.2010.12.014

Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile

Chang Keun Lim
, Jangwon Seo
, Sehoon Kim^*
, Ick Chan Kwon
, Cheol Hee Ahn
, Soo Young Park

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

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 ∼ 5.1).

Original language	English
Pages (from-to)	284-289
Number of pages	6
Journal	Dyes and Pigments
Volume	90
Issue number	3
DOIs	https://doi.org/10.1016/j.dyepig.2010.12.014
Publication status	Published - 2011 Sept

Bibliographical note

Funding Information:
This work was supported by the Real-Time Molecular Imaging Project and the Pioneer Research Program (2009-0081523) funded by the Korea Ministry of Education, Science and Technology (MEST). The work at Seoul National University was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by MEST (CRI; RIAMIAM0209(0417-20090011) ).

Keywords

Biopolymeric conjugate
Excited-state intramolecular proton transfer (ESIPT)
Fluorescent nanoparticle
Ratiometric fluorescence sensor
Self-assembly
pH sensor

ASJC Scopus subject areas

General Chemical Engineering
Process Chemistry and Technology

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10.1016/j.dyepig.2010.12.014

Cite this

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title = "Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile",

abstract = "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 (pKa ∼ 5.1).",

keywords = "Biopolymeric conjugate, Excited-state intramolecular proton transfer (ESIPT), Fluorescent nanoparticle, Ratiometric fluorescence sensor, Self-assembly, pH sensor",

author = "Lim, \{Chang Keun\} and Jangwon Seo and Sehoon Kim and Kwon, \{Ick Chan\} and Ahn, \{Cheol Hee\} and Park, \{Soo Young\}",

note = "Funding Information: This work was supported by the Real-Time Molecular Imaging Project and the Pioneer Research Program (2009-0081523) funded by the Korea Ministry of Education, Science and Technology (MEST). The work at Seoul National University was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by MEST (CRI; RIAMIAM0209(0417-20090011) ).",

year = "2011",

month = sep,

doi = "10.1016/j.dyepig.2010.12.014",

language = "English",

volume = "90",

pages = "284--289",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier B.V.",

number = "3",

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T1 - Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile

AU - Lim, Chang Keun

AU - Seo, Jangwon

AU - Kim, Sehoon

AU - Kwon, Ick Chan

AU - Ahn, Cheol Hee

AU - Park, Soo Young

N1 - Funding Information: This work was supported by the Real-Time Molecular Imaging Project and the Pioneer Research Program (2009-0081523) funded by the Korea Ministry of Education, Science and Technology (MEST). The work at Seoul National University was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by MEST (CRI; RIAMIAM0209(0417-20090011) ).

PY - 2011/9

Y1 - 2011/9

N2 - 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 (pKa ∼ 5.1).

AB - 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 (pKa ∼ 5.1).

KW - Biopolymeric conjugate

KW - Excited-state intramolecular proton transfer (ESIPT)

KW - Fluorescent nanoparticle

KW - Ratiometric fluorescence sensor

KW - Self-assembly

KW - pH sensor

UR - https://www.scopus.com/pages/publications/79952370631

U2 - 10.1016/j.dyepig.2010.12.014

DO - 10.1016/j.dyepig.2010.12.014

M3 - Article

AN - SCOPUS:79952370631

SN - 0143-7208

VL - 90

SP - 284

EP - 289

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 3

ER -

Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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