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

^*Corresponding author for this work

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

12 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

Bibliographical 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:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

amphiphiles
bioimaging
fluorescence switching
pH responsiveness
self-assembly
supramolecular chemistry

ASJC Scopus subject areas

Analytical Chemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/cptc.202000023

Cite this

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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",

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doi = "10.1002/cptc.202000023",

language = "English",

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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

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.

KW - amphiphiles

KW - bioimaging

KW - fluorescence switching

KW - pH responsiveness

KW - self-assembly

KW - supramolecular chemistry

UR - https://www.scopus.com/pages/publications/85086151982

U2 - 10.1002/cptc.202000023

DO - 10.1002/cptc.202000023

M3 - Article

AN - SCOPUS:85086151982

SN - 2367-0932

VL - 4

SP - 393

EP - 397

JO - ChemPhotoChem

JF - ChemPhotoChem

IS - 6

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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