Visible-Light-Driven Triplet Sensitization of Polycyclic Aromatic Hydrocarbons Using Thionated Perinones

The Journal of Physical Chemistry Letters
Jonathan R PalmerFelix N Castellano

Abstract

Metal-free chromophores that efficiently generate triplet excited states represent promising alternatives with respect to transition metal-containing photosensitizers, such as those featuring metal-to-ligand charge transfer excited states. However, such molecular constructs have remained underexplored due to the unclear relationship(s) between molecular structure and efficient/rapid intersystem crossing. In this regard, we present a series of three thionated perinone chromophores serving as a newly conceived class of heavy metal-free triplet photosensitizers. We demonstrate that thionation of the lone C═O substituent in each highly fluorescent perinone imparts red-shifted absorbance bands that maintain intense extinction coefficients across the visible spectrum, as well as unusually efficient triplet excited state formation as inferred from the measured singlet O2 quantum yields at 1270 nm (ΦΔ = 0.78-1.0). Electronic structure calculations revealed the emergence of a low energy S1 (n → π*) excited state in the proximity of a slightly higher energy S2 (π → π*) excited state. The distinct character in each of the two lowest-lying singlet state manifolds resulted in the energetic inversion of the corresponding triplet excited stat...Continue Reading

References

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Citations

Nov 20, 2021·The Journal of Physical Chemistry Letters·Rongchuan Su, Zhenmei Huang
Nov 19, 2021·Angewandte Chemie·Meng LvJinquan Chen

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