Halogenated BODIPY as generators of singlet oxygen

ORTIZ MJ; AGARRABEITIA AR; DURAN-SAMPEDRO G; ARBELOA T; MASSAD WA; MONTEJANO HA; GARCÍA NA; LÓPEZ ARBELOA I

Granada

Jornada; III Jornadas Ibéricas de Fotoquímica.; 2011

Spanish group of Photochemistry (GRUFO) - Sociedade Portuguesa de Química.

In the present work we report three series of iodinates BODYPYs. The synthetic method allows obtained mono, di, tri or tetraiodinated derivatives controlling also the position in which they are anchored. We should emphasize that these are the first examples of BODIPY dyes with more than two halogens in the BODIPY core. Quantum mechanic simulations of the electronic charge distribution and electrostatic potential of the BODIPY derivatives predict those chromophoric positions more suitable to the electrophilic attack by the iodine atom (considering also steric reasons), thus explaining the experimentally observed regioselectivity in the iodination.