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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012100
Subject(s) - chirality (physics) , conjugated system , supramolecular chemistry , chemical physics , self assembly , crystallography , molecule , materials science , hydrogen bond , chemistry , nanotechnology , crystal structure , chiral symmetry breaking , symmetry breaking , physics , polymer , quantum mechanics , organic chemistry , nambu–jona lasinio model , composite material
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.