ИСТИНА

Boron-dipyrrins, metal-dipyrrins and H-dipyrrins are studied for multitude of applications. As peripheral functionalization plays a pivotal role in controlling their optical properties search for novel pathways to modify dipyrrin core is of a general interest. Inspired by the pioneering work of Dehaen et.al. [1] and further developments of the method [2] we explore a nucleophilic substitution approach in dihalo-H-dipyrrins. This approach is complementary to the nucleophilic substitution–BF2 removal sequence [3]. A series of H-dipyrrins and their BODIPY derivatives substituted with redox-active substituents have been synthesized. H-dipyrrins have been converted to the corresponding Ni complexes. For BODIPY and metal derivatives, their redox properties have been measured. These measurements together with the results of quantum chemical calculations made it possible to propose the sites of primary oxidation and reduction. Solvent-dependent UV-Vis and fluorescence spectra have been determined, as well as the fluorescence quantum yields.