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On-Surface Driven Formal Michael Addition Produces m-Polyaniline Oligomers on Pt(111).
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Dec 14; Vol. 59 (51), pp. 23220-23227. Date of Electronic Publication: 2020 Oct 12. - Publication Year :
- 2020
-
Abstract
- 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.<br /> (© 2020 The Authors. Published by Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 59
- Issue :
- 51
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 32761699
- Full Text :
- https://doi.org/10.1002/anie.202009863