| 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 |
| DOI |
10.3390/molecules27010023 |
| Full Text |
|
| Is Part of |
Molecules.. Basel : MDPI AG. 2022, vol. 27, iss. 1, art. no. 23, p. 1-14.. eISSN 1420-3049 |
| Keywords [eng] |
fluorescent probes ; microviscosity ; molecular rotors ; photophysics ; polarity sensing |
| Abstract [eng] |
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. |
| Published |
Basel : MDPI AG |
| Type |
Journal article |
| Language |
English |
| Publication date |
2022 |
| CC license |
|
