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Cyclotrimerization‐Induced Chiral Supramolecular Structures of 4‐Ethynyltriphenylamine on Au(111) Surface
Authors:Feifei Xiang  Yan Lu  Chao Li  Xin Song  Xiaoqing Liu  Zhongping Wang  Juan Liu  Dr. Mingdong Dong  Prof. Dr. Li Wang
Affiliation:1. Department of Physics, Nanchang University, Xuefu Road 999, Nanchang, 330031 (P.R. China);2. Nanoscience and Nanotechnology Laboratory, Institute for Advanced Study, Nanchang University, Xuefu Road 999, Nanchang, 330031 (P.R. China);3. Interdisciplinary Nanoscience Center (iNANO), Aarhus University, 8000 Aarhus C (Denmark)
Abstract: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 species—1,3,5‐tris[4‐(diphenylamino)phenyl]benzene (TPAPB)—after annealing at 323 K. Further annealing drives these cyclotrimerized TPAPB molecules to form chiral hexagonal supramolecular structures with an extraordinary self‐healing ability.
Keywords:chirality  cycloaddition  scanning probe microscopy  self‐assembly  surface chemistry
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