Synthesis and photo-property of 2-cyano boron-dipyrromethene and the application for detecting fluoride ion

• Published in: Tetrahedron Vol. 71; no. 52; pp. 9611 - 9616
• Main Authors: Wang, Jianbo, Zong, Qianshou, Wu, Qingqing, Shen, Jinjin, Dai, Fengyuan, Wu, Chenjun
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.12.2015; Elsevier
• Subjects: Bodipy derivatives; Chemistry; Chemistry, Organic; Colorimetric sensor; Fluoride ion; High selectivity; Physical Sciences; Science & Technology; Bodipy derivatives; High selectivity; Fluoride ion; Colorimetric sensor; BODIPY DYES; REAGENTS; CHEMOSENSORS; FLUORESCENCE; CHEMISTRY; RECEPTORS; DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2015.10.081

Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CB1–CB3) have been synthesized and characterized. The photophysical properties of these compounds are investigated by means of UV/Vis absorption and fluorescence spectroscopy. CB1–CB3 exhibit small Stokes shift and high fluorescence quantum yield. Noticeably, CB2 with styrene moieties at 5-position of BODIPY displays absorption alternation with maximum of 120 nm red-shift upon addition of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as a base, giving remarkable color change which can be detected by naked eye. Meanwhile, the compound CB3 shows high selectivity toward fluoride ion via fluorescence quenching mechanism by release of the masked phenolate form of CB2 through fluoride ion induced deprotection reaction. It also exhibits fast signal response time (30 s) and excellent selectivity over other competing analytes, making it a good candidate as colorimetric sensor for fluoride sensing. [Display omitted]