5-Bromo-4,5-bis(dimethylamino)fluorescein: Synthesis and photophysical studies

Jun Yeon Hwang; Jung Yean Lee; Chang Woo Cho; Wonjun Choi; Yejin Lee; Sangdeok Shim; Gil Tae Hwang

doi:10.3390/molecules23010219

5-Bromo-4,5-bis(dimethylamino)fluorescein: Synthesis and photophysical studies

Jun Yeon Hwang, Jung Yean Lee, Chang Woo Cho, Wonjun Choi, Yejin Lee, Sangdeok Shim, Gil Tae Hwang

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Abstract

In this study, three new fluorescein derivatives—5-bromo-4',5'-dinitrofluorescein (BDNF), 5-bromo-4',5'-diaminofluorescein (BDAF), and 5-bromo-4',5'-bis(dimethylamino)fluorescein (BBDMAF)—were synthesized and their pH-dependent protolytic equilibria were investigated. In particular, BBDMAF exhibited pH-dependent fluorescence, showing strong emission only at pH 3–6. BBDMAF bears a bromine moiety and thus, can be used in various cross-coupling reactions to prepare derivatives and take advantage of its unique emission properties. To confirm this, the Suzuki and Sonogashira reactions of BBDMAF with phenylboronic acid and phenylacetylene, respectively, were performed, and the desired products were successfully obtained.

Original language	English
Article number	219
Journal	Molecules
Volume	23
Issue number	1
DOIs	https://doi.org/10.3390/molecules23010219
State	Published - 2018

Keywords

Fluorescein
Fluorescent probes
Fluorophore
PH-sensitive probes
Suzuki coupling

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10.3390/molecules23010219

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title = "5-Bromo-4,5-bis(dimethylamino)fluorescein: Synthesis and photophysical studies",

abstract = "In this study, three new fluorescein derivatives—5-bromo-4',5'-dinitrofluorescein (BDNF), 5-bromo-4',5'-diaminofluorescein (BDAF), and 5-bromo-4',5'-bis(dimethylamino)fluorescein (BBDMAF)—were synthesized and their pH-dependent protolytic equilibria were investigated. In particular, BBDMAF exhibited pH-dependent fluorescence, showing strong emission only at pH 3–6. BBDMAF bears a bromine moiety and thus, can be used in various cross-coupling reactions to prepare derivatives and take advantage of its unique emission properties. To confirm this, the Suzuki and Sonogashira reactions of BBDMAF with phenylboronic acid and phenylacetylene, respectively, were performed, and the desired products were successfully obtained.",

keywords = "Fluorescein, Fluorescent probes, Fluorophore, PH-sensitive probes, Suzuki coupling",

author = "Hwang, {Jun Yeon} and Lee, {Jung Yean} and Cho, {Chang Woo} and Wonjun Choi and Yejin Lee and Sangdeok Shim and Hwang, {Gil Tae}",

note = "Publisher Copyright: {\textcopyright} 2018 by the authors.",

year = "2018",

doi = "10.3390/molecules23010219",

language = "English",

volume = "23",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - 5-Bromo-4,5-bis(dimethylamino)fluorescein

T2 - Synthesis and photophysical studies

AU - Hwang, Jun Yeon

AU - Lee, Jung Yean

AU - Cho, Chang Woo

AU - Choi, Wonjun

AU - Lee, Yejin

AU - Shim, Sangdeok

AU - Hwang, Gil Tae

PY - 2018

Y1 - 2018

N2 - In this study, three new fluorescein derivatives—5-bromo-4',5'-dinitrofluorescein (BDNF), 5-bromo-4',5'-diaminofluorescein (BDAF), and 5-bromo-4',5'-bis(dimethylamino)fluorescein (BBDMAF)—were synthesized and their pH-dependent protolytic equilibria were investigated. In particular, BBDMAF exhibited pH-dependent fluorescence, showing strong emission only at pH 3–6. BBDMAF bears a bromine moiety and thus, can be used in various cross-coupling reactions to prepare derivatives and take advantage of its unique emission properties. To confirm this, the Suzuki and Sonogashira reactions of BBDMAF with phenylboronic acid and phenylacetylene, respectively, were performed, and the desired products were successfully obtained.

AB - In this study, three new fluorescein derivatives—5-bromo-4',5'-dinitrofluorescein (BDNF), 5-bromo-4',5'-diaminofluorescein (BDAF), and 5-bromo-4',5'-bis(dimethylamino)fluorescein (BBDMAF)—were synthesized and their pH-dependent protolytic equilibria were investigated. In particular, BBDMAF exhibited pH-dependent fluorescence, showing strong emission only at pH 3–6. BBDMAF bears a bromine moiety and thus, can be used in various cross-coupling reactions to prepare derivatives and take advantage of its unique emission properties. To confirm this, the Suzuki and Sonogashira reactions of BBDMAF with phenylboronic acid and phenylacetylene, respectively, were performed, and the desired products were successfully obtained.

KW - Fluorescein

KW - Fluorescent probes

KW - Fluorophore

KW - PH-sensitive probes

KW - Suzuki coupling

UR - http://www.scopus.com/inward/record.url?scp=85041003681&partnerID=8YFLogxK

U2 - 10.3390/molecules23010219

DO - 10.3390/molecules23010219

M3 - Article

C2 - 29361711

AN - SCOPUS:85041003681

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 1

M1 - 219

ER -

5-Bromo-4,5-bis(dimethylamino)fluorescein: Synthesis and photophysical studies

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Keywords

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