Charge‐Transfer Character in a Covalent Diketopyrrolopyrrole Dimer: Implications for Singlet Fission

Mauck, Catherine M.; Bae, Youn Jue; Chen, Michelle; Powers‐Riggs, Natalia; Wu, Yi‐Lin; Wasielewski, Michael R.

doi:10.1002/cptc.201700135

Charge‐Transfer Character in a Covalent Diketopyrrolopyrrole Dimer: Implications for Singlet Fission

Journal Article · Thu Oct 12 00:00:00 EDT 2017 · ChemPhotoChem

DOI:https://doi.org/10.1002/cptc.201700135· OSTI ID:1399161

Mauck, Catherine M. ^[1]; Bae, Youn Jue ^[1]; Chen, Michelle ^[1]; Powers‐Riggs, Natalia ^[1]; Wu, Yi‐Lin ^[1]; ^[1]

Department of Chemistry, Argonne-Northwestern Solar Energy Research (ANSER) Center, Institute for Sustainability and Energy at Northwestern Northwestern University Evanston IL 60208-3113 USA

Abstract

Diketopyrrolopyrrole (DPP) is a strongly absorbing, photostable chromophore that can undergo singlet fission (SF), a photophysical process that promises to significantly enhance solar‐cell performance. In the solid state, DPP packs in a herringbone arrangement that maximizes intermolecular donor–acceptor interactions, suggesting that charge‐transfer (CT) states play a role in DPP SF. In order to characterize intermolecular DPP CT states in molecular assemblies, we have synthesized a covalent DPP dimer bridged by a xanthene linker, which places two thiophene‐substituted DPPs (TDPPs) in a cofacial arrangement that mimics chromophore π–π stacking in the thin film. After photoexcitation in polar solvents, symmetry‐breaking charge separation forms the fully charge separated TDPP ^+. –TDPP ^−. ion‐pair state. In nonpolar solvents, charge separation is incomplete leading to the TDPP ^δ+ –TDPP ^δ− CT state, which is in pseudoequilibrium with the relaxed S ₁ S ₀ state observed by transient absorption and emission spectroscopy. This study highlights the importance of intramolecular coupling as well as the importance of entropy to promoting SF in chromophore dimers for which SF is endo‐ or isoergic.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; FG02-99ER14999

OSTI ID:: 1399161

Journal Information:: ChemPhotoChem, Journal Name: ChemPhotoChem Journal Issue: 3 Vol. 2; ISSN 2367-0932

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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