Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses

Ted M. Pappenfus, Furqan Almyahi, Nathan A. Cooling, Evan W. Culver, Seth C. Rasmussen, Paul C. Dastoor

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    6 Scopus citations

    Abstract

    This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3-hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2-methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β-defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large-scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.

    Original languageEnglish (US)
    Article number1800272
    JournalMacromolecular Chemistry and Physics
    Volume219
    Issue number21
    DOIs
    StatePublished - Nov 2018

    Bibliographical note

    Funding Information:
    T.M.P. acknowledges the following: i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research, the UMM Division of Science and Mathematics, and the Howard Hughes Medical Institute (HHMI) Pathways to Science Program for financial assistance, ii) Eric King and Nathan Ferrey for investigating the very first DArP reactions in green solvents in 2014, and iii) Andrew J. Helmin and Wyatt D. Wilcox for assistance with the GPC experiments and for helpful discussions. S.C.R. acknowledges the Australian-American Fulbright Commission and North Dakota State University for financial support. The work was performed in part at the Materials node of the Australian National Fabrication Facility, a company established under the National Collaborative Research Infrastructure Strategy to provide nano-and micro-fabrication facilities for Australia’s researchers.

    Publisher Copyright:
    © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

    Keywords

    • direct arylation scalability
    • organic solar cells
    • polythiophenes

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