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

Research output: Contribution to journalArticle

134 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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Excitons
Thin films
Perylene
Photosynthesis
Photoexcitation
Thick films
X-Ray Diffraction
Crystal structure
Vapors
Derivatives
X ray diffraction
LDS 751
perylenediimide
Organic solar cells

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • 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., ... 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

Singlet exciton fission in polycrystalline thin films of a slip-stacked perylenediimide. / Eaton, Samuel W.; Shoer, Leah E.; Karlen, Steven D.; Dyar, Scott M.; Margulies, Eric A.; Veldkamp, Brad S.; Ramanan, Charusheela; Hartzler, Daniel A.; Savikhin, Sergei; Marks, Tobin J; Wasielewski, Michael R.

In: Journal of the American Chemical Society, Vol. 135, No. 39, 02.10.2013, p. 14701-14712.

Research output: Contribution to journalArticle

Eaton, SW, Shoer, LE, Karlen, SD, Dyar, SM, Margulies, EA, Veldkamp, BS, Ramanan, C, Hartzler, DA, Savikhin, S, Marks, TJ & Wasielewski, MR 2013, 'Singlet exciton fission in polycrystalline thin films of a slip-stacked perylenediimide', Journal of the American Chemical Society, vol. 135, no. 39, pp. 14701-14712. https://doi.org/10.1021/ja4053174
Eaton SW, Shoer LE, Karlen SD, Dyar SM, Margulies EA, Veldkamp BS et al. Singlet exciton fission in polycrystalline thin films of a slip-stacked perylenediimide. Journal of the American Chemical Society. 2013 Oct 2;135(39):14701-14712. https://doi.org/10.1021/ja4053174
Eaton, Samuel W. ; Shoer, Leah E. ; Karlen, Steven D. ; Dyar, Scott M. ; Margulies, Eric A. ; Veldkamp, Brad S. ; Ramanan, Charusheela ; Hartzler, Daniel A. ; Savikhin, Sergei ; Marks, Tobin J ; Wasielewski, Michael R. / Singlet exciton fission in polycrystalline thin films of a slip-stacked perylenediimide. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 39. pp. 14701-14712.
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AU - Dyar, Scott M.

AU - Margulies, Eric A.

AU - Veldkamp, Brad S.

AU - Ramanan, Charusheela

AU - Hartzler, Daniel A.

AU - Savikhin, Sergei

AU - Marks, Tobin J

AU - Wasielewski, Michael R

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N2 - 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.

AB - 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.

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