Design of singlet fission chromophores with cyclic (alkyl)(amino) carbene building blocks

Achini Japahuge, Seunghoon Lee, Cheol Ho Choi, Tao Zeng

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41 Scopus citations

Abstract

We use MRSF-TDDFT and NEVPT2 methods to design singlet fission chromophores with the building blocks of cyclic (alkyl)(amino)carbenes (CAACs). CAAC dimers with C2, C4, and p-phenylene spacers are considered. The substitutions with trifluoromethyls and fluorine atoms at the α C position are investigated. The electronegative substituents enhance the π accepting capability of the α C while maintaining it as a quaternary C atom. The phenylene-connected dimers with the two substitutions are identified as promising candidates for singlet fission chromophores. The cylindrically symmetric C2 and C4 spacers allow for substantial structural reorganizations in the S0-to-S1 and S0-to-T1 excitations. Although the two substituted dimers with the C4 spacer satisfy (or very close to satisfy) the primary thermodynamics criterion for singlet fission, the significant structural reorganizations result in high barriers so that the fission is kinetically unfavorable.

Original languageEnglish
Article number234306
JournalJournal of Chemical Physics
Volume150
Issue number23
DOIs
StatePublished - 21 Jun 2019

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