Synthesis and photo-physical properties of a series of BODIPY dyes

A series of 39 boron-dipyrrolylmethenes (BODIPYs) have been synthesized and characterized. Their spectroscopic properties, degree of lipophilicity, chemical stability under irradiation, and singlet-oxygen generation rate have also been studied. These compounds differ in the presence of ethyl groups (group A), hydrogens (group B) or iodines (group C) on the 2,6 positions; these appendices confer particular characteristics to each group. The presence of an aromatic substituent or hydrogen on the indacene 8 position produces 13 different molecules of each group. Besides the effects exerted by the group or atom on the 2,6 positions, the substituent on the 8 position exerts a further effect on the physico-chemical parameters, thus the desired properties of BODIPYs, concerning fluorescence, lipophilicity, and singlet oxygen production can be modulated accordingly.

Graphical abstractDownload full-size imageThirty-nine BODIPYs, divided into three groups depending on the substituent on the 2,6 positions, were synthesized and some of their physico-chemical properties, such as absorption and emission spectra, HPLC retention times, singlet-oxygen generation, and stability toward photodegradation, were determined and discussed.