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- Title
Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors.
- Authors
Maleckaitė, Karolina; Narkevičius, Domantas; Žilėnaitė, Rugilė; Dodonova-Vaitkūnienė, Jelena; Toliautas, Stepas; Tumkevičius, Sigitas; Vyšniauskas, Aurimas
- 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 ( E a ) for non-radiative relaxation affects the probe's sensitivity to temperature and viscosity and provide appropriate E a ranges for the best possible sensitivity to viscosity and temperature.
- Subjects
STAINS &; staining (Microscopy); FLUORESCENCE spectroscopy; QUANTUM wells; DENSITY functional theory; ACTIVATION energy; POLARITY (Chemistry)
- Publication
Molecules, 2022, Vol 27, Issue 1, p23
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27010023