Ultra-pH-Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change

Junjie Cui; Gayoung Kim; Sehoon Kim; Ji Eon Kwon; Soo Young Park

doi:10.1002/cptc.202000023

Ultra-pH-Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change

Junjie Cui, Gayoung Kim, Sehoon Kim, Ji Eon Kwon, Soo Young Park

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

4 Citations (Scopus)

Abstract

We synthesized an amphiphilic small molecule 1 by attaching oligo(ethylene glycol) (OEG) and N,N-diethylamine (DEA) units to a fluorescent dicyanodistyrylbenzene (DCS) core. The molecule is fully soluble in aqueous solution at low pH (pH<4.3) by protonation of the DEA groups; but, above pH 4.3, it self-assembles to form nanoparticles due to increased hydrophobicity upon deprotonation, leading to a ratiometric fluorescence color change from green emission in the monomeric form (λ_em,max=538 nm) to red emission in the aggregated form (λ_em,max=646 nm). It should be noted that the ratio of emission intensities at 538 nm and 646 nm (R=I₅₃₈/I₆₄₆) changes drastically about 42-fold within a very narrow pH range of 4.3–4.6.

Original language	English
Pages (from-to)	393-397
Number of pages	5
Journal	ChemPhotoChem
Volume	4
Issue number	6
DOIs	https://doi.org/10.1002/cptc.202000023
Publication status	Published - 2020 Jun 1
Externally published	Yes

Keywords

amphiphiles
bioimaging
fluorescence switching
pH responsiveness
self-assembly
supramolecular chemistry

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Analytical Chemistry

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10.1002/cptc.202000023

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title = "Ultra-pH-Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change",

abstract = "We synthesized an amphiphilic small molecule 1 by attaching oligo(ethylene glycol) (OEG) and N,N-diethylamine (DEA) units to a fluorescent dicyanodistyrylbenzene (DCS) core. The molecule is fully soluble in aqueous solution at low pH (pH<4.3) by protonation of the DEA groups; but, above pH 4.3, it self-assembles to form nanoparticles due to increased hydrophobicity upon deprotonation, leading to a ratiometric fluorescence color change from green emission in the monomeric form (λem,max=538 nm) to red emission in the aggregated form (λem,max=646 nm). It should be noted that the ratio of emission intensities at 538 nm and 646 nm (R=I538/I646) changes drastically about 42-fold within a very narrow pH range of 4.3–4.6.",

keywords = "amphiphiles, bioimaging, fluorescence switching, pH responsiveness, self-assembly, supramolecular chemistry",

author = "Junjie Cui and Gayoung Kim and Sehoon Kim and Kwon, {Ji Eon} and Park, {Soo Young}",

note = "Funding Information: This work was supported by the Basic Science Research Program through the NRF funded by the Ministry of Science, ICT and Future Planning (Grant No. 2017R1E1A1A01075372 [RIAM0417‐20190019]). Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

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doi = "10.1002/cptc.202000023",

language = "English",

volume = "4",

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T1 - Ultra-pH-Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change

AU - Cui, Junjie

AU - Kim, Gayoung

AU - Kim, Sehoon

AU - Kwon, Ji Eon

AU - Park, Soo Young

N1 - Funding Information: This work was supported by the Basic Science Research Program through the NRF funded by the Ministry of Science, ICT and Future Planning (Grant No. 2017R1E1A1A01075372 [RIAM0417‐20190019]). Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/6/1

Y1 - 2020/6/1

N2 - We synthesized an amphiphilic small molecule 1 by attaching oligo(ethylene glycol) (OEG) and N,N-diethylamine (DEA) units to a fluorescent dicyanodistyrylbenzene (DCS) core. The molecule is fully soluble in aqueous solution at low pH (pH<4.3) by protonation of the DEA groups; but, above pH 4.3, it self-assembles to form nanoparticles due to increased hydrophobicity upon deprotonation, leading to a ratiometric fluorescence color change from green emission in the monomeric form (λem,max=538 nm) to red emission in the aggregated form (λem,max=646 nm). It should be noted that the ratio of emission intensities at 538 nm and 646 nm (R=I538/I646) changes drastically about 42-fold within a very narrow pH range of 4.3–4.6.

AB - We synthesized an amphiphilic small molecule 1 by attaching oligo(ethylene glycol) (OEG) and N,N-diethylamine (DEA) units to a fluorescent dicyanodistyrylbenzene (DCS) core. The molecule is fully soluble in aqueous solution at low pH (pH<4.3) by protonation of the DEA groups; but, above pH 4.3, it self-assembles to form nanoparticles due to increased hydrophobicity upon deprotonation, leading to a ratiometric fluorescence color change from green emission in the monomeric form (λem,max=538 nm) to red emission in the aggregated form (λem,max=646 nm). It should be noted that the ratio of emission intensities at 538 nm and 646 nm (R=I538/I646) changes drastically about 42-fold within a very narrow pH range of 4.3–4.6.

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KW - fluorescence switching

KW - pH responsiveness

KW - self-assembly

KW - supramolecular chemistry

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Ultra-pH-Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change

Abstract

Keywords

ASJC Scopus subject areas

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