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- Title
5-Bromo-4',5'-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies.
- Authors
Hwang, Jun Yeon; Lee, Jung-Yean; Cho, Chang-Woo; Choi, Wonjun; Lee, Yejin; Shim, Sangdeok; Hwang, Gil Tae
- 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 pH3-6. BBDMAF bears a brominemoiety 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.
- Subjects
FLUORESCEIN; BROMINE compounds; ETHYNYL benzene; HYDROGEN-ion concentration; SUZUKI reaction; COUPLING reactions (Chemistry)
- Publication
Molecules, 2018, Vol 23, Issue 1, p219
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23010219