Structure-enabled long-lived charge separation in single crystals of an asymmetric donor–acceptor perylenediimide cyclophane

Williams, Malik L.; Coleman, Adam F.; Peinkofer, Kathryn R.; Young, Ryan M.; Wasielewski, Michael R.

doi:10.1039/d4sc03359k

Chem. Sci.

2024

DOI: 10.1039/d4sc03359k

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Structure-enabled long-lived charge separation in single crystals of an asymmetric donor–acceptor perylenediimide cyclophane

Malik L. Williams,

Adam F. Coleman,

Kathryn R. Peinkofer

et al.

Abstract: Pre-organizing donor–acceptor structural motifs to elicit specific crystal morphologies can lead to enhanced photogenerated charge carrier lifetimes for solar energy conversion.

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Polarity of Ordered Solvent Molecules in 9,9′-Bianthracene Single Crystals Selects between Singlet Fission or Symmetry-Breaking Charge Separation

Peinkofer,

Williams,

Mantel

et al. 2024

J. Am. Chem. Soc.

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Singlet exciton fission (SF) and symmetry-breaking charge separation (SB-CS) are both photophysical processes that can occur between two organic chromophores and are both of interest to improve solar energy conversion. Here, we tuned the photophysics of a 9,9′-bianthracene (BA) single crystal between SF and SB-CS using solvent intercalation to change the electric field within the crystal. Crystals of BA were grown in o-xylene, chlorobenzene, odichlorobenzene, and benzonitrile, as well as solvent-free from a melt. The crystals were studied by X-ray diffraction, steady-state optical spectroscopy, and transient absorption microscopy to elucidate the role of the intercalated solvent molecules. The crystals with no solvent in the structure undergo fast SF (<2 ps), while the crystals with intercalated moderately polar solvents o-xylene, chlorobenzene, and o-dichlorobenzene show evidence of chargetransfer-mediated SF. Finally, the crystals containing highly polar benzonitrile undergo SB-CS instead of SF. These results demonstrate that controlling solvation of BA in the crystal structure can tune its photophysics between SF and SB-CS.

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Polarity of Ordered Solvent Molecules in 9,9′-Bianthracene Single Crystals Selects between Singlet Fission or Symmetry-Breaking Charge Separation

Peinkofer,

Williams,

Mantel

et al. 2024

J. Am. Chem. Soc.

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show abstract

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Structure-enabled long-lived charge separation in single crystals of an asymmetric donor–acceptor perylenediimide cyclophane

Abstract: Pre-organizing donor–acceptor structural motifs to elicit specific crystal morphologies can lead to enhanced photogenerated charge carrier lifetimes for solar energy conversion.

Cited by 1 publication

References 33 publications

Polarity of Ordered Solvent Molecules in 9,9′-Bianthracene Single Crystals Selects between Singlet Fission or Symmetry-Breaking Charge Separation

Polarity of Ordered Solvent Molecules in 9,9′-Bianthracene Single Crystals Selects between Singlet Fission or Symmetry-Breaking Charge Separation

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