On-Surface Driven Formal Michael Addition Produces m-Polyaniline Oligomers on Pt(111)

Ruiz del Árbol, N. ; Sánchez-Sánchez, C. ; Otero-Irurueta, G. ; Martínez, J.I. ; de Andrés, P.L. ; Gómez-Herrero, A.C. ; Merino, P. ; Piantek, M. ; Serrate, D. (Universidad de Zaragoza) ; Lacovig, P. ; Lizzit, S. ; Alemán, J. ; Ellis, G.J. ; López, M.F. ; Martín-Gago, J.A.

Resumen: 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.

Idioma: Inglés

DOI: 10.1002/anie.202009863

Año: 2020

Publicado en: Angewandte Chemie (International ed.) 59, 11 (2020), 23220-23227
ISSN: 1433-7851

Factor impacto JCR: 15.336 (2020)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 16 / 178 = 0.09 (2020) - Q1 - T1

Factor impacto SCIMAGO: 5.831 - Chemistry (miscellaneous) (Q1) - Catalysis (Q1)

Financiación: info:eu-repo/grantAgreement/EC/FP7/610256/EU/Gas and Dust from the Stars to the Laboratory: Exploring the NanoCosmos/NANOCOSMOS
Financiación: info:eu-repo/grantAgreement/EC/H2020/785219/EU/Graphene Flagship Core Project 2/GrapheneCore2
Financiación: info:eu-repo/grantAgreement/EC/H2020/881603/EU/Graphene Flagship Core Project 3/GrapheneCore3
Financiación: info:eu-repo/grantAgreement/ES/MINECO/MAT2017-85089-C2-1-R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/RYC-2015-17730

Tipo y forma: Article (Published version)

Área (Departamento): Área Física Materia Condensada (Dpto. Física Materia Condensa.)