On-surface homocoupling reactivity of a chiral bifunctional bromoindanone molecule on Cu(111)

On-surface synthesis has provided exciting concepts for the building of covalently bonded molecular nanostructures as well as the exploration of new synthetic pathway alternatives to chemical synthesis in solution. The surface-supported reaction of precursor molecules can result in the formation of...

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Bibliographic Details
Published inNew journal of chemistry Vol. 46; no. 47; pp. 22869 - 22876
Main Authors Hussein, Fatima, Pigot, Corentin, Romero Lairado, Francisco, Minissale, Marco, Salomon, Eric, Angot, Thierry, Dumur, Frdric, Nechab, Malek, Gigmes, Didier, Clair, Sylvain, Giovanelli, Luca
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 05.12.2022
Royal Society of Chemistry [1987-....]
Subjects
Adsorption
Chemical bonds
Chemical Sciences
Chemical synthesis
Condensed Matter
Coupling (molecular)
Enantiomers
Low temperature
Material chemistry
Materials Science
Molecular structure
Photoelectric emission
Physics
Precursors
Racemization
Scanning tunneling microscopy
Surface chemistry
Ultrahigh vacuum
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Summary:On-surface synthesis has provided exciting concepts for the building of covalently bonded molecular nanostructures as well as the exploration of new synthetic pathway alternatives to chemical synthesis in solution. The surface-supported reaction of precursor molecules can result in the formation of 2D molecular networks as well as novel 0D molecular structures. In this study, we investigate the adsorption of a chiral molecule ( R )-6-bromo-3-phenyl-2,3-dihydro-1 H -inden-1-one (BrPhINDO) on the Cu(111) surface under ultrahigh vacuum conditions by low-temperature scanning tunneling microscopy and core-level photoemission spectroscopy. Annealing an as-deposited layer of molecules allows two kinds of homocoupling reactions to be activated, the Ullmann-like coupling reaction and the Knoevenagel reaction, resulting in the formation of various low-dimensional structures. By studying their prochirality and comparing with the products obtained using an enantiomer precursor, we demonstrate adsorption-induced chiral inversion inducing partial racemization. Sequential reactivity is creating various kinds of macromolecular compounds with distinct prochirality using an on-surface synthesis approach.
Bibliography:https://doi.org/10.1039/d2nj04708j
Electronic supplementary information (ESI) available. See DOI
ISSN:1144-0546
1369-9261
DOI:10.1039/d2nj04708j