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In this article, we present synthesis, spectral characteristics, and results of DFT calculations of new CH(R)-bis(BODIPY) 1-3. They are characterized by the conformational mobility and sensitivity of fluorescence to polarity, proton-, electron donor ability and viscosity of the solvation environment. It is shown that fluorescence intensity of 1-3 increases in the homologous series of alcohols (ethanol, 1-propanol, 1-butanol, 1-octanol, 1-decanol) mainly due to decrease of medium acidic properties. The viscosity of the medium effects on the 1-3 fluorescence in a lesser degree. Compared to 1 and 2, the 3 is the most sensitive towards viscosity both in low-viscosity homologous alcohols and in high-viscosity ethanol-glycerol mixtures. In this regard, the sensitivity of fluorescence of CH(MeOPh)-bis(BODIPY) (compound 3) to the viscosity was studied in binary mixtures of polar DMF and low-polarity toluene with castor and vaseline oils, as well as to the macroviscosity of the solvate environment in mixtures of toluene with polystyrene. Prospects of the practical application of CH(R)-bis(BODIPY)s are proposed for the analysis of polarity, proton-donor properties and viscosity of the medium.
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| http://dx.doi.org/10.1016/j.saa.2021.120393 | DOI Listing |
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