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Synthesis and Two‐Dimensional Chiral Surface Self‐Assembly of a π‐Conjugated System with Three‐Fold Symmetry: Benzotri(7‐Azaindole)
Author(s) -
Rodríguez Luis M.,
Gómez Paula,
MásMontoya Miriam,
Abad José,
Tárraga Alberto,
Cerdá Jorge I.,
Méndez Javier,
Curiel David
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012100
Subject(s) - chirality (physics) , supramolecular chemistry , conjugated system , crystallography , self assembly , molecule , chemistry , chemical physics , hydrogen bond , supramolecular chirality , materials science , stereochemistry , nanotechnology , crystal structure , chiral symmetry breaking , symmetry breaking , physics , polymer , organic chemistry , quantum mechanics , nambu–jona lasinio model
Abstract The synthesis of a novel expanded π‐conjugated system, namely benzotri(7‐azaindole), BTAI, is reported. Its C 3 h symmetry along with the integration of six complementary donor and acceptor N−H⋅⋅⋅N hydrogen bonds in the conjugated structure promote the 2D self‐assembly on Au(111) over extended areas. Besides, a perfect commensurability with the gold lattice endows the physisorbed molecular film with a remarkable stability. The structural features of BTAI result in two levels of surface chirality: Firstly, the molecules become chiral upon adsorption on the surface. Then, due to the favorable N−H⋅⋅⋅N hydrogen bond‐directed self‐assembly, along with the relative molecular rotation with respect to the substrate, supramolecular chirality manifests in two mirror enantiomorphous domains. Thus, the system undergoes spontaneous chiral resolution. LEED and STM assisted by theoretical simulations have been employed to characterize in detail these novel 2D conglomerates with relevant chiral properties for systems with C 3 h symmetry.