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

Siyuan Zhang, Junxiang Zhang, Maged Abdelsamie, Qinqin Shi, Yadong Zhang, Timothy C. Parker, Evgheni V. Jucov, Tatiana V. Timofeeva, Aram Amassian, Guillermo C. Bazan, Simon B. Blakey, Stephen Barlow, Seth R. Marder

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15 Scopus citations


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%.
Original languageEnglish (US)
Pages (from-to)7880-7887
Number of pages8
JournalChemistry of Materials
Issue number18
StatePublished - Sep 5 2017

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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).


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