Hole-Transporting Materials based on Oligo(hetero)aryls with a Naphthodithiophene Core – Succinct Synthesis by Twofold Direct C−H Olefination

Chia Chi Hsu, Kun Mu Lee, Xiao Wei Wu, Li Lin, Wei Lun Yu, Ching Yuan Liu

Research output: Contribution to journalArticlepeer-review

Abstract

This work demonstrated the first synthetic application of direct C−H olefinations in the step-saving preparation of various hole-transporting materials (HTM) for efficient perovskite solar cells (PSC). Cross-dehydrogenative couplings of naphthodithiophene (NDT) with vinyl arenes under palladium-catalysis facilely generated various new oligo(hetero)aryls with internal alkenes. Reaction conditions were optimized, which gave the product isolated yields of up to 71 % with high (E)-stereoselectivity. These readily accessible NDT core-based small molecules involving olefin as π-spacers displayed immediate power conversion efficiencies of up to 17.2 % without a device oxidation process that is required for the commercially available spiro-OMeTAD and most other existing HTMs while fabricated in corresponding PSC devices.

Original languageEnglish
Article numbere202302552
JournalChemistry - A European Journal
Volume30
Issue number10
DOIs
StatePublished - 16 Feb 2024

Keywords

  • Direct C−H Olefination
  • Hole-Transporting Material
  • Naphthodithiophene
  • Perovskite Solar Cell
  • Synthesis Design

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