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Keywords:

  • copolymerization;
  • donor–acceptor systems;
  • photovoltaics;
  • polymers;
  • solar cells

Abstract

Pentacyclic diindeno[1,2-b:2′,1′-d]thiophene (DIDT) unit is a rigid and coplanar conjugated molecule. To the best of our knowledge, this attractive molecule has never been incorporated into a polymer and thus its application in polymer solar cells has never been explored. For the first time, we report the detailed synthesis of the tetra-alkylated DIDT molecule leading to its dibromo- and diboronic ester derivatives, which are the key monomers for preparation of DIDT-based polymers. Two donor–acceptor alternating polymers, poly(diindenothiophene-alt-benzothiadiazole) PDIDTBT and poly(diindenothiophene-alt-dithienylbenzothiadiazole) PDIDTDTBT, were synthesized by using Suzuki polymerization. Copolymer PTDIDTTBT was also prepared by using Stille polymerization. Although PTDIDTTBT is prepared through a manner of random polymerization, we found that the different reactivities of the dibromo-monomers lead to the resulting polymer having a block copolymer arrangement. With the higher structural regularity, PTDIDTTBT, symbolized as (thiophene-alt-DIDT)0.5-block-(thiophene-alt-BT)0.5, shows the higher degree of crystallization, stronger π–π stacking, and broader absorption spectrum in the solid state, as compared to its alternating PDIDTDTBT analogue. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. PDIDTDTBT/PC71BM and PTDIDTTBT/PC71BM systems exhibited promising power-conversion efficiencies (PCEs) of 1.65 % and 2.00 %, respectively. Owing to the complementary absorption spectra, as well as the compatible structures of PDIDTDTBT and PTDIDTTBT, the PCE of the device based on the ternary blend PDIDTDTBT/PTDIDTTBT/PC71BM was further improved to 2.40 %.

Featured Compounds

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  1. 1 - 16
Compound DIDT
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound PDIDTBT
Molecular Weight:841.346
Molecular Formula:(C56H76N2S2)n
InChIKey:Not Available
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Compound PDIDTDTBT
Molecular Weight:1005.593
Molecular Formula:(C64H80N2S4)n
InChIKey:Not Available
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Compound PTDIDTTBT
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound CPDT
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound TPT
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound PTDIDT
Molecular Weight:789.311
Molecular Formula:(C54H76S2)n
InChIKey:Not Available
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Compound 1
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:QNXSIUBBGPHDDE-UHFFFAOYSA-N
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Compound 2
Molecular Weight:262.3026
Molecular Formula:C18H14O2
InChIKey:Not Available
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Compound 3
Molecular Weight:260.353
Molecular Formula:C18H12S
InChIKey:Not Available
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Compound 4
Molecular Weight:709.203
Molecular Formula:C50H76S
InChIKey:Not Available
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Compound 5
Molecular Weight:866.996
Molecular Formula:C50H74Br2S
InChIKey:Not Available
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Compound 6
Molecular Weight:961.126
Molecular Formula:C62H98B2O4S
InChIKey:Not Available
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Compound 7
Molecular Weight:293.966
Molecular Formula:C6H2Br2N2S
InChIKey:FEOWHLLJXAECMU-UHFFFAOYSA-N
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Compound 8
Molecular Weight:458.214
Molecular Formula:C14H6Br2N2S3
InChIKey:Not Available
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Compound 9
Molecular Weight:409.75
Molecular Formula:C10H20SSn2
InChIKey:Not Available
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  1. 1 - 16