Substitution of hydroxide by fluoride at the boron center of a BODIPY dye Academic Article

abstract

• 4-Chloro-4-phenyl-1,3,5,7,8-pentamethyl-3a,4a-diaza-4-bora-s-indacene (2) has been synthesized, structurally characterized and converted into the corresponding hydroxide derivative 4-hydroxo-4-phenyl-1,3,5,7,8-pentamethyl-3a, 4a-diaza-4-bora-s-indacene (3). This boron hydroxide derivative reacts with fluoride anions under acidic conditions to afford the corresponding fluoride derivative 4-fluoro-4-phenyl-1,3,5,7,8-pentamethyl-3a,4a-diaza-4-bora-s-indacene (4). This simple reaction may become useful for the incorporation of [ 18F]-fluoride and may serve for the preparation of radiolabeled BODIPY derivatives. 2010 Elsevier B.V.

authors

• Gabbai, Francois

published proceedings

• JOURNAL OF FLUORINE CHEMISTRY

altmetric score

• 6

author list (cited authors)

• Hudnall, T. W., Lin, T., & Gabbai, F. P.

citation count

• 34

complete list of authors

• Hudnall, Todd W||Lin, Tzu-Pin||Gabbaii, Francois P

publication date

• November 2010

publisher

• Elsevier  Publisher

published in

• Journal of Fluorine Chemistry  Journal

keywords

• Bodipy
• Dye
• FLUORESCENCE
• Fluoride
• Fluorination
• Sensing

Digital Object Identifier (DOI)

• 10.1016/j.jfluchem.2010.06.012

start page

• 1182

end page

• 1186

volume

• 131

issue

• 11

URL

• http://dx.doi.org/10.1016/j.jfluchem.2010.06.012