Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 28, Pages 8582-8586Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804110
Keywords
ab initio calculations; charge transfer; photoelectron spectroscopy; scanning probe microscopy; surface chemistry
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Funding
- Graphene Flagship Core2-Graphene-based disruptive technologies EU Horizon 2020 [785219]
- ERC-synergy program [ERC-2013-SYG-610256 Nanocosmos]
- CTI-CSIC
- Spanish MINECO [MAT2017-85089-C2-1-R, MAT2014-54231-C4-1-P, MAT2014-54231-C4-4-P]
- Czech GACR funding [17-24210Y]
- Czech Academy of Sciences through the Praemium Academiae award [LM2015087]
- FCT program [IF/01054/2015]
- NATIONAL CENTER FOR COMPLEMENTARY &ALTERNATIVE MEDICINE [F05AT002014] Funding Source: NIH RePORTER
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On-surface synthesis is an emerging approach to obtain, in a single step, precisely defined chemical species that cannot be obtained by other synthetic routes. The control of the electronic structure of organic/metal interfaces is crucial for defining the performance of many optoelectronic devices. A facile on-surface chemistry route has now been used to synthesize the strong electron-acceptor organic molecule quinoneazine directly on a Cu(110) surface, via thermally activated covalent coupling of para-aminophenol precursors. The mechanism is described using a combination of insitu surface characterization techniques and theoretical methods. Owing to a strong surface-molecule interaction, the quinoneazine molecule accommodates 1.2 electrons at its carbonyl ends, inducing an intramolecular charge redistribution and leading to partial conjugation of the rings, conferring azo-character at the nitrogen sites.
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