Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 26, Pages 9346-9354Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja501680n
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Funding
- ERC Advanced Grant MolArt [247299]
- Munich Center for Advanced Photonics (MAP)
- Technische Universitat Munchen-Institute - German Research Foundation (DFG) via the German Excellence Initiative
- Marie Curie Intra-European Fellowship (project NASUMECA) [274842]
- International Max Planck Research School of Advanced Photon Science (IMPRS-APS)
- International Center for Young Scientists (ICYS)
- International Center for Materials Nanoarchitectonics (MANA)
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The templated synthesis of porphyrin dimers, oligomers, and tapes has recently attracted considerable interest. Here, we introduce a clean, temperature-induced covalent dehydrogenative coupling mechanism between unsubstituted free-base porphine units yielding dimers, trimers, and larger oligomers directly on a Ag(111) support under ultrahigh-vacuum conditions. Our multitechnique approach, including scanning tunneling microscopy, near-edge X-ray absorption fine structure and photoelectron spectroscopy complemented by theoretical modeling, allows a comprehensive characterization of the resulting nanostructures and sheds light on the coupling mechanism. We identify distinct coupling motifs and report a decrease of the electronic gap and a modification of the frontier orbitals directly associated with the formation of triply fused dimeric species. This new on-surface homocoupling protocol yields covalent porphyrin nanostructures addressable with submolecular resolution and provides prospective model systems towards the exploration of extended oligomers with tailored chemical and physical properties.
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