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J Am Chem Soc. 2013 Oct 2;135(39):14701-12. doi: 10.1021/ja4053174. Epub 2013 Sep 23.

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

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Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University , 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States.


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 τ(SF) = 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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