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dc.contributor.authorZhang, Ke
dc.contributor.authorWucher, Philipp
dc.contributor.authorMarszalek, Tomasz
dc.contributor.authorBabics, Maxime
dc.contributor.authorRingk, Andreas
dc.contributor.authorBlom, Paul W. M.
dc.contributor.authorBeaujuge, Pierre
dc.contributor.authorPisula, Wojciech
dc.date.accessioned2021-07-07T07:41:38Z
dc.date.available2021-07-07T07:41:38Z
dc.date.issued2018-07-14
dc.date.submitted2018-03-27
dc.identifier.citationZhang, K., Wucher, P., Marszalek, T., Babics, M., Ringk, A., Blom, P. W. M., … Pisula, W. (2018). Long-Range Molecular Self-Assembly from π-Extended Pyrene-Functionalized Diketopyrrolopyrroles. Chemistry of Materials, 30(15), 5032–5040. doi:10.1021/acs.chemmater.8b01276
dc.identifier.issn1520-5002
dc.identifier.issn0897-4756
dc.identifier.doi10.1021/acs.chemmater.8b01276
dc.identifier.urihttp://hdl.handle.net/10754/670049
dc.description.abstractEnd-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.
dc.description.sponsorshipP.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.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/acs.chemmater.8b01276
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in CHEMISTRY OF MATERIALS, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.chemmater.8b01276.
dc.titleLong-Range Molecular Self-Assembly from pi-Extended Pyrene-Functionalized Diketopyrrolopyrroles
dc.typeArticle
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.contributor.departmentMaterial Science and Engineering Program
dc.contributor.departmentKAUST Solar Center (KSC)
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.identifier.journalCHEMISTRY OF MATERIALS
dc.rights.embargodate2019-07-14
dc.identifier.wosutWOS:000442186500022
dc.eprint.versionPost-print
dc.contributor.institutionMax Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
dc.contributor.institutionDepartment of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
dc.identifier.volume30
dc.identifier.issue15
dc.identifier.pages5032-5040
kaust.personWucher, Philipp
kaust.personBabics, Maxime
kaust.personRingk, Andreas
kaust.personBeaujuge, Pierre
kaust.grant.numberCRG_R2_13_BEAU_KAUST_1
dc.date.accepted2018-07-09
dc.identifier.eid2-s2.0-85049885649
kaust.acknowledged.supportUnitBaseline Research Funding
kaust.acknowledged.supportUnitCRG
kaust.acknowledged.supportUnitKAUST ACL
kaust.acknowledged.supportUnitOffice of Sponsored Research (OSR)


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