Conjugate-like addition of soft nucleophiles to 8-alkenylBODIPYs

Enrique Alvarado-Martínez, Eduardo Peña-Cabrera

Departamento de Química. Universidad de Guanajuato. Noria Alta S/N. Guanajuato, Gto. 36050, Mexico

Adv. Mater. Lett., 2018, 9 (6), pp 426-431

DOI: 10.5185/amlett.2018.1859

Publication Date (Web): May 17, 2018

E-mail: eduardop@ugto.mx

Abstract


Meso-phenylethenylBODIPY 8 was prepared using the Liebeskind-Srogl cross-coupling reaction. The reactivity of 8 was evaluated in the addition of soft nucleophiles observing that, in all the cases studied, the addition took place exclusively at the b-alkene position with good chemical yields under mild conditions. While the starting BODIPY 8 was non-emissive, all of the adducts were highly fluorescent in MeOH, except for meso-coumarinBODIPY 11. However, when the fluorescence of 11 was measured in EtOAc, a 41-fold increase was observed. This behaviour was explained in terms of a photoinduced electron-transfer phenomenon. 

Keywords

BODIPY, meso-alkenylBODIPY, conjugate addition, fluorescence.

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