Long-Range Molecular Self-Assembly from pi-Extended Pyrene-Functionalized Diketopyrrolopyrroles

Ke Zhang, Philipp Wucher, Tomasz Marszalek, Maxime Babics, Andreas Ringk, Paul W. M. Blom, Pierre Beaujuge, Wojciech Pisula

Research output: Contribution to journalArticlepeer-review

21 Scopus citations


End-group-directed molecular self-assembly can be an effective strategy in the design of "organic electronics" amenable to specific morphologies and charge transport patterns for device applications. In this study, we report on the design, self-ordering, and transistor characteristics of an analogous set of pyrene-functionalized diketopyrrolopyrroles (DPP; namely, SM1-3) obtained by "successive incorporation" of DPP motifs. The well-defined pyrene-substituted DPP analogues are systematically examined in correlation of (i) the number of incorporated DPP motifs in the π-extended main-chain and (ii) the solution-processing conditions employed for the thin film formation. Solvent vapor enhanced drop-casting (SVED) from chloroform (CHCl3 ) and tetrahydrofuran (THF) are found to promote very distinct, long-range morphologies of SM1-3. During THF-mediated SVED, the growth of a one-dimensional fiber of SM1-3 originates from the formation of initial aggregates in THF. In particular, extending the π-conjugation of the DPP core, and, concurrently, the number of alkyl side-chains involved, is found to mitigate the long-range self-assembly of SM1-3 and, in turn, to lower crystal size and fiber length. Field-effect transistors based on SM3 exhibit ambipolar behavior, demonstrating the relevance of pyrene-functionalized diketopyrrolopyrroles in the design and development of solution-processed ambipolar small-molecule semiconductors.
Original languageEnglish (US)
Pages (from-to)5032-5040
Number of pages9
Issue number15
StatePublished - Jul 14 2018

Bibliographical note

KAUST Repository Item: Exported on 2021-12-14
Acknowledged KAUST grant number(s): CRG_R2_13_BEAU_KAUST_1
Acknowledgements: P.M.B. acknowledges concurrent support from the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Award No. CRG_R2_13_BEAU_KAUST_1 and under Baseline Research Funding. P.W. thanks the KAUST ACL for technical support in the mass spectrometry analyses. K.Z. thanks the China Scholarship Council (CSC) for financial support. W.P. acknowledges National Science Centre, Poland, through the grant UMO-2015/18/E/ST3/00322.

ASJC Scopus subject areas

  • Materials Chemistry
  • Chemical Engineering(all)
  • Chemistry(all)


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