Singlet Fission in Carbene Derived Diradicaloids

Angewandte Chemie
Tobias UllrichDirk M Guldi

Abstract

In large, the documentation of singlet fission (SF) is showcased in examples involving polyacenes and polyenes. SF has been hitherto studied in depth, on one hand, in solids and, on the other hand, in solutions, in which cases covalent bridges are required to link two or more chromophores. Going beyond polyacenes and polyenes is driven by exploring new classes of SF-materials. Herein, we present a new class of SF-materials based on diradicaloids of carbene scaffolds, namely cyclic (alkyl)(amino)carbenes (CAACs). Our modular approach allows for tuning two key SF-criteria: the steric factor and the diradical character. In turn, we modified the energy landscapes of excited states in a systematic manner to accommodate the needs for SF. We report the first example on intermolecular SF in solutions for CAAC dimers formed via self-assembly at cryogenic temperatures.

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Citations

Nov 11, 2020·Chemistry : a European Journal·Hyunho KimEunsung Lee
Jan 27, 2021·Chemical Society Reviews·Tobias UllrichDirk M Guldi
Jan 21, 2021·Chemistry : a European Journal·Mahendra K SharmaRajendra S Ghadwal
Apr 13, 2021·Journal of the American Chemical Society·Long WangHongbing Fu
Apr 27, 2021·Journal of the American Chemical Society·Yuki MiyazawaManabu Abe
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joanna StoychevaAlia Tadjer
Jun 15, 2021·Chemical Science·Avijit MaitiAnukul Jana
Jul 27, 2021·The Journal of Physical Chemistry. a·Vladimir I MinkinAlyona A Starikova
Dec 2, 2020·The Journal of Physical Chemistry. a·Piermaria Pinter, Dominik Munz

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Methods Mentioned

BETA
NMR

Software Mentioned

NEVPT2
fsTA
nsTA

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