On‐Surface Bottom‐Up Synthesis of Azine Derivatives Displaying Strong Acceptor Behavior

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....

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2018-07, Vol.130 (28), p.8718-8722
Main Authors: Ruiz del Árbol, Nerea, Palacio, Irene, Otero‐Irurueta, Gonzalo, Martínez, José I., de Andrés, Pedro L., Stetsovych, Oleksander, Moro‐Lagares, María, Mutombo, Pingo, Svec, Martin, Jelínek, Pavel, Cossaro, Albano, Floreano, Luca, Ellis, Gary J., López, María F., Martín‐Gago, José A.
Format: Article
Language:English
Subjects:
Ab-initio-Rechnungen
Aminophenol
Carbonyls
Chemical speciation
Chemical synthesis
Chemistry
Conjugation
Copper
Electronic structure
Interfaces
Ladungstransfer
Molecular chains
Oberflächenchemie
Optoelectronic devices
Organic chemistry
Photoelektronenspektroskopie
Rastersondenverfahren
Surface chemistry
Surface properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 in situ 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. Mit einer einfachen Oberflächenmethode wurde das stark elektronenakzeptierende organische Molekül Chinonazin durch thermisch aktivierte kovalente Kupplung von para‐Aminophenol‐Vorstufen direkt auf Cu(110) synthetisiert. Der Mechanismus wurde anhand von In‐situ‐Oberflächencharakterisierung und Rechnungen beschrieben. Wegen einer starken Oberfläche‐Molekül‐Wechselwirkung befinden sich 1.2 Elektronen an den Carbonylenden des Chinonazin‐Moleküls.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201804110