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On‐Surface Bottom‐Up Synthesis of Azine Derivatives Displaying Strong Acceptor Behavior
Author(s) -
Ruiz del Árbol Nerea,
Palacio Irene,
OteroIrurueta Gonzalo,
Martínez José I.,
de Andrés Pedro L.,
Stetsovych Oleksander,
MoroLagares María,
Mutombo Pingo,
Svec Martin,
Jelínek Pavel,
Cossaro Albano,
Floreano Luca,
Ellis Gary J.,
López María F.,
MartínGago José A.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804110
Subject(s) - molecule , intramolecular force , covalent bond , chemistry , redistribution (election) , electron acceptor , acceptor , azine , chemical physics , photochemistry , nanotechnology , combinatorial chemistry , materials science , computational chemistry , stereochemistry , organic chemistry , physics , condensed matter physics , politics , political science , law
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.