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Issue 6, 2016
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Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors

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Abstract

A series of perylenediimide (PDI) dimers are evaluated as acceptors for organic photovoltaic (OPV) cells. The materials are characterized using a wide variety of physical and computational techniques. These dimers are first linked at the bay position of each PDI molecule via an aromatic spacer; subsequent photocyclization affords ring-fused dimers. Thus, photocyclization of the thiophene-linked dimer 2,5-bis-[N,N′-bis-perylenediimide-1-yl]-thiophene (T1) affords the twisted acceptor [2,3-b:2′,3′-d]-bis-[N,N′-bis-perylenediimide-1,12-yl]-thiophene (T2), while photocyclization of the thienothiophene-linked dimer, 2,5-bis-[N,N′-bis-perylenediimide-1-yl]-thienothiophene (TT1) affords the planar acceptor [2,3-b:2′,3′-d]-bis-[N,N′-bis-perylenediimide-1,12-yl]-thienothiophene (TT2). Furthermore, a dimer linked by a phenylene group, 1,4-bis-[N,N′-bis-perylenediimide-1-yl]-benzene (Ph1), can be selectively photocyclized to form either the twisted dimer, [1,2:3,4]-bis-[N,N′-bis-perylenediimide-1,12-yl]-benzene (Ph1a) or the planar dimer [1,2:4,5]-bis-[N,N′-bis-perylenediimide-1,12-yl]-benzene (Ph2b). Ring-fusion results in increased electronic coupling between the PDI units, and increased space-charge limited thin film electron mobility. While charge transport is efficient in bulk-heterojunction blends of each dimer with the polymeric donor PBDTT-FTTE, in the case of the twisted dimers ring fusion leads to a significant decrease in geminate recombination, hence increased OPV photocurrent density and power conversion efficiency. This effect is not observed in planar dimers where ring fusion leads to increased crystallinity and excimer formation, decreased photocurrent density, and decreased power conversion efficiency. These results argue that ring fusion is an effective approach to increasing OPV bulk-heterojunction charge carrier generation efficiency in PDI dimers as long as they remain relatively amorphous, thereby suppressing excimer formation and coulombically trapped charge transfer states.

Graphical abstract: Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors

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Publication details

The article was received on 23 Dec 2015, accepted on 01 Feb 2016 and first published on 09 Feb 2016


Article type: Edge Article
DOI: 10.1039/C5SC04956C
Chem. Sci., 2016,7, 3543-3555
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors

    P. E. Hartnett, H. S. S. R. Matte, N. D. Eastham, N. E. Jackson, Y. Wu, L. X. Chen, M. A. Ratner, R. P. H. Chang, M. C. Hersam, M. R. Wasielewski and T. J. Marks, Chem. Sci., 2016, 7, 3543
    DOI: 10.1039/C5SC04956C

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