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Twisted Anthracene-Fused BODIPY: Intersystem Crossing and Torsion-Induced Non-Radiative Relaxation of the Singlet Excited State
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Twisted Anthracene-Fused BODIPY: Intersystem Crossing and Torsion-Induced Non-Radiative Relaxation of the Singlet Excited State
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Journal Article
Twisted Anthracene-Fused BODIPY: Intersystem Crossing and Torsion-Induced Non-Radiative Relaxation of the Singlet Excited State
2026
Overview
The photophysical properties of a BODIPY derivative with the highly twisted molecular structure of anthracene-fused boron–dipyrromethene (AN-BDP) were studied with steady-state and time-resolved spectroscopic methods. The fused anthryl and the BDP units in AN-BDP units both adopt distorted geometry (with ca. 10° of torsion), and there is large dihedral angle between the two units (ca. 49.7°). Interestingly, the fluorescence quantum yields are highly dependent on the solvent polarity (59~3%, from toluene to acetonitrile), yet the fluorescence emission wavelength does not change in different solvents. Nanosecond transient absorption spectra indicate that the triplet state is long-lived, with an intrinsic triplet state lifetime of 551 μs. Interestingly the severely twisted structure only shows a moderate intersystem crossing (ISC) yield (10%). Femtosecond transient absorption spectra indicate slow ISC (>1.5 ns), which is in agreement with the fluorescence lifetime (2.3 ns). Time-resolved electron paramagnetic resonance (TREPR) spectra show smaller zero-field-splitting D and E tensors as (−71.4 mT, 16.7 mT, respectively) compared to the triplet state of the iodinated native BDP (D = −104.6 mT, E = 22.8 mT), inferring that the triplet-state wave function of the new compound is delocalized over the twisted molecular framework. The theoretical computation indicated a solvent-polarity-dependent energy barrier for the relaxed S1 state to a conical interaction (CI) of the S1 and the S0 state potential curves, which agrees with the weaker fluorescence in polar solvents.
Publisher
MDPI AG,Multidisciplinary Digital Publishing Institute (MDPI)
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