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5-Bromo-4',5'-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies
Jun Yeon Hwang1, Jung-Yean Lee2, Chang-Woo Cho3
1Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Korea. gghog@naver.com.
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.
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