Cyclotrimerization-Induced Chiral Supramolecular Structures of 4-Ethynyltriphenylamine on Au(111) Surface

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DOI

  • Feifei Xiang, Nanchang Univ, Nanchang University, Nanosci & Nanotechnol Lab, Inst Adv Study, Denmark
  • Yan Lu, Nanchang Univ, Nanchang University, Dept Phys
  • ,
  • Chao Li, Nanchang Univ, Nanchang University, Dept Phys
  • ,
  • Xin Song
  • ,
  • Xiaoqing Liu, Nanchang Univ, Nanchang University, Dept Phys, Denmark
  • Zhongping Wang, Nanchang Univ, Nanchang University, Dept Phys, Denmark
  • Juan Liu, Nanchang Univ, Nanchang University, Dept Phys, Denmark
  • Mingdong Dong

Cyclotrimerization-induced chiral supramolecular structures of 4-ethynyltriphenylamine (ETPA) have been synthesized on the Au(111) surface through alkyne-based reactions. Whereas the ETPA molecules adsorbed on the Au(111) surface remain inert and form a close-packed self-assembled structure at room temperature, the combination of scanning tunneling microscopy observations and theoretical calculations unambiguously reveal that the ETPA molecules cyclotrimerize to form new trimer-like species1,3,5-tris[4-(diphenylamino)phenyl]benzene (TPAPB)after annealing at 323K. Further annealing drives these cyclotrimerized TPAPB molecules to form chiral hexagonal supramolecular structures with an extraordinary self-healing ability.

Original languageEnglish
JournalChemistry: A European Journal
Volume21
Issue37
Pages (from-to)12978-12983
Number of pages6
ISSN0947-6539
DOIs
Publication statusPublished - 7 Sep 2015

    Research areas

  • chirality, cycloaddition, scanning probe microscopy, self-assembly, surface chemistry, SCANNING-TUNNELING-MICROSCOPY, AZIDE-ALKYNE CYCLOADDITION, TOTAL-ENERGY CALCULATIONS, WAVE BASIS-SET, TERMINAL ALKYNES, GRAPHENE NANORIBBONS, THERMAL-STABILITY, SOLID-STATE, NOBLE-METAL, POLYMERIZATION

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