Singlet exciton fission in polycrystalline thin films of a slip-stacked perylenediimide

Samuel W. Eaton, Leah E. Shoer, Steven D. Karlen, Scott M. Dyar, Eric A. Margulies, Brad S. Veldkamp, Charusheela Ramanan, Daniel A. Hartzler, Sergei Savikhin, Tobin J. Marks, Michael R. Wasielewski

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169 Citations (Scopus)

Abstract

The crystal structure of N,N-bis(n-octyl)-2,5,8,11-tetraphenylperylene-3,4: 9,10-bis(dicarboximide), 1, obtained by X-ray diffraction reveals that 1 has a nearly planar perylene core and π-π stacks at a 3.5 Å interplanar distance in well-separated slip-stacked columns. Theory predicts that slip-stacked, π-π-stacked structures should enhance interchromophore electronic coupling and thus favor singlet exciton fission. Photoexcitation of vapor-deposited polycrystalline 188 nm thick films of 1 results in a 140 ± 20% yield of triplet excitons (3*1) in τSF = 180 ± 10 ps. These results illustrate a design strategy for producing perylenediimide and related rylene derivatives that have the optimized interchromophore electronic interactions which promote high-yield singlet exciton fission for potentially enhancing organic solar cell performance and charge separation in systems for artificial photosynthesis.

Original languageEnglish
Pages (from-to)14701-14712
Number of pages12
JournalJournal of the American Chemical Society
Volume135
Issue number39
DOIs
Publication statusPublished - Oct 2 2013

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Eaton, S. W., Shoer, L. E., Karlen, S. D., Dyar, S. M., Margulies, E. A., Veldkamp, B. S., Ramanan, C., Hartzler, D. A., Savikhin, S., Marks, T. J., & Wasielewski, M. R. (2013). Singlet exciton fission in polycrystalline thin films of a slip-stacked perylenediimide. Journal of the American Chemical Society, 135(39), 14701-14712. https://doi.org/10.1021/ja4053174