On-Surface Driven Formal Michael Addition Produces m-Polyaniline Oligomers on Pt(111).
DFT
Polyaniline
coupling reactions
nc-AFM/STM
on-surface synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
14 Dec 2020
14 Dec 2020
Historique:
received:
17
07
2020
pubmed:
8
8
2020
medline:
8
8
2020
entrez:
8
8
2020
Statut:
ppublish
Résumé
On-surface synthesis is emerging as a highly rational bottom-up methodology for the synthesis of molecular structures that are unattainable or complex to obtain by wet chemistry. Here, oligomers of meta-polyaniline, a known ferromagnetic polymer, were synthesized from para-aminophenol building-blocks via an unexpected and highly specific on-surface formal 1,4 Michael-type addition at the meta position, driven by the reduction of the aminophenol molecule. We rationalize this dehydrogenation and coupling reaction mechanism with a combination of in situ scanning tunneling and non-contact atomic force microscopies, high-resolution synchrotron-based X-ray photoemission spectroscopy and first-principles calculations. This study demonstrates the capability of surfaces to selectively modify local molecular conditions to redirect well-established synthetic routes, such as Michael coupling, towards the rational synthesis of new covalent nanostructures.
Identifiants
pubmed: 32761699
doi: 10.1002/anie.202009863
pmc: PMC7116460
mid: EMS105440
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
23220-23227Subventions
Organisme : European Research Council
ID : 610256
Pays : International
Organisme : Ministerio de Economía, Industria y Competitividad, Gobierno de España
ID : MAT2017-85089-C2-1-R
Organisme : FP7 Ideas: European Research Council
ID : 610256
Organisme : H2020 Future and Emerging Technologies
ID : 881608
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
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