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Keywords:

  • free-radical phosphanylation;
  • fluorescence;
  • heteroacenes;
  • organic semiconductors;
  • phospholes

Abstract

Ladder-type oligophenylenes (LOPP) with bridging heteroatoms are interesting systems as they offer novel electronic and photophysical properties on account of the rigid structural features, more efficient electron delocalization on the coplanar aromatic framework, and strong intermolecular interactions. LOPPs incorporating multiple phosphorous centers combine the excellent electronic properties of phospholes and rigidified conjugated framework of LOPPs, thus positioning themselves as an attractive class of organic semiconductors. To date, there still lacks an effective synthetic methodology towards LOPPs with multiple phosphorous bridges. Herein, we describe the synthesis and properties of a new class of bisphosphole-bridged ladder oligo(p-phenylene)s and the related phosphoxides. The synthesis of phospholes was achieved by a four-fold free-radical phosphanylation reaction of a tetrabromo p-terphenylene or biphenyl-thiophene. Sequential trapping of four highly reactive aryl radicals occurred effectively to give the desired phosphorous-containing ladder compound. The oxides of the phospholes are shown to be strong fluorophores that can be used as potential n-type building blocks for organic semiconducting materials.

Featured Compounds

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  1. 1 - 16
Compound 2a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1b
Molecular Weight:290.402
Molecular Formula:C18H10S2
InChIKey:ICDSCKCHUNSGRV-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1d
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound P1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound P2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound trans-2a
Molecular Weight:442.4273
Molecular Formula:C30H20P2
InChIKey:ULNOGPXSXVZXJY-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:545.888
Molecular Formula:C18H10Br4
InChIKey:BRXVFKOIXGTYLP-UHFFFAOYSA-N
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Compound trans-3a
Molecular Weight:474.4261
Molecular Formula:C30H20O2P2
InChIKey:ZSWSHGRBCURZIQ-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:551.916
Molecular Formula:C16H8Br4S
InChIKey:VKKIEBYCFATULC-UHFFFAOYSA-N
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Compound 5
Molecular Weight:516.793
Molecular Formula:C12H6Br3I
InChIKey:JARJBILEICNSTH-UHFFFAOYSA-N
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Compound 6
Molecular Weight:206.853
Molecular Formula:C4H4BBrO2S
InChIKey:GGPJEVFFYNCPJV-UHFFFAOYSA-N
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Compound trans-2b
Molecular Weight:448.455
Molecular Formula:C28H18P2S
InChIKey:UYQBKBCWZUAQIV-UHFFFAOYSA-N
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Compound trans-3b
Molecular Weight:480.454
Molecular Formula:C28H18O2P2S
InChIKey:VOMYVWSIQNDKSO-UHFFFAOYSA-N
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