On-Surface Synthesis of Polyphenylene Wires Comprising Rigid Aliphatic Bicyclo[1.1.1]Pentane Isolator Units

Biao Yang, Kaifeng Niu, Nan Cao, Nitika Grover, Wenchao Zhao, Alexander Riss, Jonas Björk, Willi Auwärter, Johannes V. Barth, Mathias O. Senge

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Bicyclo[1.1.1]pentane (BCP) motifs are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of benzene rings and as molecular building blocks in materials science. Herein we explore the behavior of 1,3-disubstituted BCP moieties on metal surfaces by combining low-temperature scanning tunneling microscopy / non-contact atomic force microscopy studies with density functional theory modeling. We examine the configuration of individual BCP-containing precursors on Au(111), their supramolecular assembly and thermally activated dehalogenative coupling reactions, affording polymeric chains with incorporated electronically isolating units. Our studies not only provide the first sub-molecular insights of the BCP scaffold behavior on surfaces, but also extend the potential application of BCP derivatives towards integration in custom-designed surface architectures.

Original languageEnglish
Article numbere202218211
JournalAngewandte Chemie International Edition in English
Volume62
Issue number19
DOIs
StatePublished - 2 May 2023

Keywords

  • Bicyclo[1.1.1]Pentane
  • Hydrocarbons
  • Isosteres
  • On-Surface Chemistry
  • Scanning Probe Microscopy

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