Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 4, Pages 1782-1788Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202012100
Keywords
2D materials; benzotri(7-azaindole); spontaneous resolution; supramolecular surface chirality; surface self-assembly
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Funding
- Ministry of Science, Innovation and Universities [MAT2015-66888-C3-1R, MAT2017-85089-C2-1-R, RTI2018-101092-B-I00, RTI2018-097895-B-C41]
- Programa Estatal de Fomento de la Investigacion Cientifica y Tecnica de Excelencia [RED2018-102815-T]
- Fundacion Seneca-Agencia de Ciencia y Tecnologia de la Region de Murcia [20959/PI/18]
- Fundacion Seneca
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This study reports a novel expanded pi-conjugated system, BTAI, which exhibits 2D self-assembly behavior on gold surface. The molecular film formed by the self-assembly of BTAI molecules shows surface chirality and undergoes spontaneous chiral resolution due to hydrogen bond-directed supramolecular chirality.
The synthesis of a novel expanded pi-conjugated system, namely benzotri(7-azaindole), BTAI, is reported. Its C-3h 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-3h symmetry.
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