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    Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores

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    Type
    Article
    Authors
    Zhang, Siyuan
    Zhang, Junxiang
    Abdelsamie, Maged cc
    Shi, Qinqin
    Zhang, Yadong
    Parker, Timothy C. cc
    Jucov, Evgheni V.
    Timofeeva, Tatiana V. cc
    Amassian, Aram cc
    Bazan, Guillermo C. cc
    Blakey, Simon B. cc
    Barlow, Stephen cc
    Marder, Seth R. cc
    KAUST Department
    KAUST Solar Center (KSC)
    Material Science and Engineering Program
    Organic Electronics and Photovoltaics Group
    Physical Science and Engineering (PSE) Division
    Date
    2017-09-05
    Online Publication Date
    2017-09-05
    Print Publication Date
    2017-09-26
    Permanent link to this record
    http://hdl.handle.net/10754/625759
    
    Metadata
    Show full item record
    Abstract
    Two intermediate-sized donor molecules, BBTz-X and BDT-X, have been synthesized by the Stille coupling between 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b′]dithiophen-2-yl)-7-(5′-hexyl-[2,2′-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine and either 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-2,6-diiodobenzo[1,2-d:4,5-d′]bis(thiazole) or 2,6-dibromo-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene, respectively. Both oxidation and reduction potentials for BBTz-X are anodically shifted relative to those for BDT-X, but the oxidation potential is more sensitive to the identity of the core; this is consistent with what is seen for DFT-calculated HOMO and LUMO energies and with a slightly blue-shifted absorption maximum for BBTz-X. Although DFT calculations, along with crystal structures of related compounds, suggest more planar molecular structures for BBTz-X than for BDT-X, film structures and the effects of various annealing processes on these films, as revealed by GIWAXS, are similar. The performance of BDT-X:PC61BM bulk-heterojunction solar cells is more sensitive to annealing conditions than that of BBTz-X:PC61BM cells, but under appropriate conditions, both yield power conversion efficiencies of >7%.
    Citation
    Zhang S, Zhang J, Abdelsamie M, Shi Q, Zhang Y, et al. (2017) Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores. Chemistry of Materials 29: 7880–7887. Available: http://dx.doi.org/10.1021/acs.chemmater.7b02665.
    Sponsors
    The research was partly supported by the National Science Foundation, through the CCI Center for Selective C–H Functionalization (CHE-1205646 and CHE-1700982) and through the PREM program (DMR-1523611), and by the Department of the Navy, Office of Naval Research, through Award No. N00014-14-1-0580 (CAOP MURI).
    Publisher
    American Chemical Society (ACS)
    Journal
    Chemistry of Materials
    DOI
    10.1021/acs.chemmater.7b02665
    Additional Links
    http://pubs.acs.org/doi/full/10.1021/acs.chemmater.7b02665
    Relations
    Is Supplemented By:
    • [Dataset]
      Zhang, S., Zhang, J., Abdelsamie, M., Shi, Q., Zhang, Y., Parker, T. C., Jucov, E. V., Timofeeva, T. V., Amassian, A., Bazan, G. C., Blakey, S. B., Barlow, S., & Marder, S. R. (2017). CCDC 1578533: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC1PZLFP. DOI: 10.5517/ccdc.csd.cc1pzlfp Handle: 10754/663862
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.chemmater.7b02665
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Material Science and Engineering Program; KAUST Solar Center (KSC)

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