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

Molecules. 2018 Jan 20;23(1):219. doi: 10.3390/molecules23010219.

Authors

Jun Yeon Hwang¹, Jung-Yean Lee², Chang-Woo Cho³, Wonjun Choi⁴, Yejin Lee⁵, Sangdeok Shim⁶, Gil Tae Hwang⁷

Affiliations

¹ Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Korea. gghog@naver.com.
² Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Korea.
³ Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Korea. leejjung0102@gmail.com.
⁴ Department of Chemistry, Sunchon National University, 255 Jungang-ro, Sunchon, Jeonnam 57922, Korea. chl5288018@naver.com.
⁵ Department of Chemistry, Sunchon National University, 255 Jungang-ro, Sunchon, Jeonnam 57922, Korea. leeyejin710@gmail.com.
⁶ Department of Chemistry, Sunchon National University, 255 Jungang-ro, Sunchon, Jeonnam 57922, Korea. san90@scnu.ac.kr.
⁷ Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Korea. giltae@knu.ac.kr.

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: Suzuki coupling; fluorescein; fluorescent probes; fluorophore; pH-sensitive probes.

MeSH terms

Acetylene / analogs & derivatives
Acetylene / chemistry
Boronic Acids / chemistry
Fluorescein / chemical synthesis*
Fluorescent Dyes / chemical synthesis*
Hydrogen-Ion Concentration
Molecular Structure
Spectrometry, Fluorescence / methods

Substances

Boronic Acids
Fluorescent Dyes
phenylacetylene
benzeneboronic acid
Acetylene
Fluorescein