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Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors
Authors:Karolina Maleckait&#x;  Domantas Narkevi ius  Rugil&#x; il&#x;nait&#x;  Jelena Dodonova-Vaitk nien&#x;  Stepas Toliautas  Sigitas Tumkevi ius  Aurimas Vy&#x;niauskas
Institution:1.Center of Physical Sciences and Technology, Saulėtekio av. 3, LT-10257 Vilnius, Lithuania;2.Institute of Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Naugarduko str. 24, LT-03225 Vilnius, Lithuania; (D.N.); (R.Ž.); (J.D.-V.); (S.T.);3.Institute of Chemical Physics, Faculty of Physics, Vilnius University, Saulėtekio av. 9-III, LT-10222 Vilnius, Lithuania;
Abstract:Mapping microviscosity, temperature, and polarity in biosystems is an important capability that can aid in disease detection. This can be achieved using fluorescent sensors based on a green-emitting BODIPY group. However, red fluorescent sensors are desired for convenient imaging of biological samples. It is known that phenyl substituents in the β position of the BODIPY core can shift the fluorescence spectra to longer wavelengths. In this research, we report how electron-withdrawing (EWG) and -donating (EDG) groups can change the spectral and sensory properties of β-phenyl-substituted BODIPYs. We present a trifluoromethyl-substituted (EWG) conjugate with moderate temperature sensing properties and a methoxy-substituted (EDG) molecule that could be used as a lifetime-based polarity probe. In this study, we utilise experimental results of steady-state and time-resolved fluorescence, as well as quantum chemical calculations using density functional theory (DFT). We also explain how the energy barrier height (Ea) for non-radiative relaxation affects the probe’s sensitivity to temperature and viscosity and provide appropriate Ea ranges for the best possible sensitivity to viscosity and temperature.
Keywords:fluorescent probes  photophysics  molecular rotors  microviscosity  polarity sensing
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