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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.

SUBMITTER: Hwang JY

PROVIDER: S-EPMC6017165 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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5-Bromo-4',5'-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies.

Hwang Jun Yeon JY Lee Jung-Yean JY Cho Chang-Woo CW Choi Wonjun W Lee Yejin Y Shim Sangdeok S Hwang Gil Tae GT

Molecules (Basel, Switzerland) 20180120 1

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 prepar ...[more]

PMID: 29361711

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