4′,5′-Bis(dimethylamino)fluorescein Exhibits pH-Dependent Emission Behavior Distinct From That of Fluorescein

Jun Yeon Hwang; Sangdeok Shim; Gil Tae Hwang

doi:10.1002/ajoc.201700577

4′,5′-Bis(dimethylamino)fluorescein Exhibits pH-Dependent Emission Behavior Distinct From That of Fluorescein

Jun Yeon Hwang, Sangdeok Shim, Gil Tae Hwang

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

5 Scopus citations

Abstract

4′,5′-Diaminofluoresein (DAF) and 4′,5′-bis(dimethylamino)fluorescein (BDMAF) have been synthesized and their pH-dependent photophysical properties and protolytic equilibria investigated. Although the parent fluorescein exhibits decreased emission upon decreasing pH, DAF displayed quenched emission at all pH values; surprisingly, BDMAF exhibited strong fluorescence only at pH 3–6, with its emission almost completely quenched under strongly acidic, neutral, and basic conditions.

Original language	English
Pages (from-to)	150-154
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	1
DOIs	https://doi.org/10.1002/ajoc.201700577
State	Published - Jan 2018

Keywords

dyes/pigments
fluorescein
fluorescent probes
pH-sensitive probes
sensors

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10.1002/ajoc.201700577

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title = "4′,5′-Bis(dimethylamino)fluorescein Exhibits pH-Dependent Emission Behavior Distinct From That of Fluorescein",

abstract = "4′,5′-Diaminofluoresein (DAF) and 4′,5′-bis(dimethylamino)fluorescein (BDMAF) have been synthesized and their pH-dependent photophysical properties and protolytic equilibria investigated. Although the parent fluorescein exhibits decreased emission upon decreasing pH, DAF displayed quenched emission at all pH values; surprisingly, BDMAF exhibited strong fluorescence only at pH 3–6, with its emission almost completely quenched under strongly acidic, neutral, and basic conditions.",

keywords = "dyes/pigments, fluorescein, fluorescent probes, pH-sensitive probes, sensors",

author = "Hwang, {Jun Yeon} and Sangdeok Shim and Hwang, {Gil Tae}",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

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doi = "10.1002/ajoc.201700577",

language = "English",

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AU - Hwang, Jun Yeon

AU - Shim, Sangdeok

AU - Hwang, Gil Tae

PY - 2018/1

Y1 - 2018/1

N2 - 4′,5′-Diaminofluoresein (DAF) and 4′,5′-bis(dimethylamino)fluorescein (BDMAF) have been synthesized and their pH-dependent photophysical properties and protolytic equilibria investigated. Although the parent fluorescein exhibits decreased emission upon decreasing pH, DAF displayed quenched emission at all pH values; surprisingly, BDMAF exhibited strong fluorescence only at pH 3–6, with its emission almost completely quenched under strongly acidic, neutral, and basic conditions.

AB - 4′,5′-Diaminofluoresein (DAF) and 4′,5′-bis(dimethylamino)fluorescein (BDMAF) have been synthesized and their pH-dependent photophysical properties and protolytic equilibria investigated. Although the parent fluorescein exhibits decreased emission upon decreasing pH, DAF displayed quenched emission at all pH values; surprisingly, BDMAF exhibited strong fluorescence only at pH 3–6, with its emission almost completely quenched under strongly acidic, neutral, and basic conditions.

KW - dyes/pigments

KW - fluorescein

KW - fluorescent probes

KW - pH-sensitive probes

KW - sensors

UR - http://www.scopus.com/inward/record.url?scp=85036494483&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201700577

DO - 10.1002/ajoc.201700577

M3 - Article

AN - SCOPUS:85036494483

SN - 2193-5807

VL - 7

SP - 150

EP - 154

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 1

ER -

4′,5′-Bis(dimethylamino)fluorescein Exhibits pH-Dependent Emission Behavior Distinct From That of Fluorescein

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Keywords

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