Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors

Kohei Sekine, Jürgen Schulmeister, Fabian Paulus, Katelyn P. Goetz, Frank Rominger, Matthias Rudolph, Jana Zaumseil, A. Stephen K. Hashmi

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The gold-catalyzed facile synthesis of U-shaped and S-shaped bispentalenes is described from easily available tetra(arylethynyl)-benzenes and -naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U-shaped and S-shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S-shaped naphthalene-based bispentalene shows a one-dimensional face-to-face packing pattern in solid state and a good hole mobility, indicating that the S-shaped bispentalene core is highly suitable for transistor applications. The gold-catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors.

Original languageEnglish
Pages (from-to)216-220
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number1
DOIs
Publication statusPublished - Jan 2 2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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