Effect of polar protic solvents on the photophysical properties of bis(BODIPY) dyes

Abstract

In this paper, detailed comparative analysis of the spectral properties of bis(BODIPY) dyes in various organic solvents: saturated aromatic hydrocarbons, homologous series of alcohols (CnOH, n = 2–4, 8, 10) and mixture of ethanol-glycerol with different viscosity was carried out. In bis(BODIPY) dimeric molecules, the BODIPY chromophore domains are linked by a methylene spacer at the 2,2-, 2,3-, or 3,3-positions (1, 2, and 3 respectively). The absorption spectra of the bis(BODIPY)s exhibit exciton splitting of band maxima. We showed that bis(BODIPY)s are sensitive to the polarity and acidity of media due to its structural features. The mechanism of fluorescence quenching of 1–3 in the series of alcohols are explained in detail. It has been established that the fluorescence quenching efficiency of dimeric dyes in alcohols is determined by both universal and specific interactions. The fluorescence quantum yield of bis(BODIPY)s is minimal in ethanol and increases in the alcohols homologous series due to a reduction in medium polarity and the stability of the bis(BODIPY)(Solv)2 supramolecular structures. In viscous ethanol-glycerol mixtures, fluorescence of 1–3 increases because of the limitation of the dye molecules conformational mobility. The results of the study allow us to predict the possibility of practical application of 1–3 as alcohols fluorescent sensors in various media.