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Molecules 2018, 23(1), 219; https://doi.org/10.3390/molecules23010219

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

1
Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Korea
2
Department of Chemistry, Sunchon National University, 255 Jungang-ro, Sunchon, Jeonnam 57922, Korea
*
Authors to whom correspondence should be addressed.
Received: 15 December 2017 / Revised: 10 January 2018 / Accepted: 16 January 2018 / Published: 20 January 2018
(This article belongs to the Section Organic Chemistry)
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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. View Full-Text
Keywords: fluorescein; fluorophore; fluorescent probes; pH-sensitive probes; Suzuki coupling fluorescein; fluorophore; fluorescent probes; pH-sensitive probes; Suzuki coupling
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hwang, J.Y.; Lee, J.-Y.; Cho, C.-W.; Choi, W.; Lee, Y.; Shim, S.; Hwang, G.T. 5-Bromo-4′,5′-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies. Molecules 2018, 23, 219.

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