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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

294 Scopus citations


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 (US)
Pages (from-to)14701-14712
Number of pages12
JournalJournal of the American Chemical Society
Issue number39
StatePublished - Oct 2 2013

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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