Thermal selectivity of intermolecular versus intramolecular reactions on surfaces

Borja Cirera, Nelson Giménez-Agulló, Jonas Björk, Francisco Martínez-Peña, Alberto Martin-Jimenez, Jonathan Rodriguez-Fernandez, Ana M. Pizarro, Roberto Otero, José M. Gallego, Pablo Ballester (), José R. Galan-Mascaros () and David Ecija ()
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Borja Cirera: IMDEA Nanoscience, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain
Nelson Giménez-Agulló: Institute of Chemical Research of Catalonia, Barcelona Institute of Science and Technology
Jonas Björk: Chemistry and Biology, IFM, Linköping University
Francisco Martínez-Peña: IMDEA Nanoscience, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain
Alberto Martin-Jimenez: IMDEA Nanoscience, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain
Jonathan Rodriguez-Fernandez: Universidad Autónoma de Madrid, c/Francisco Tomás y Valiente 7, Cantoblanco, 28049 Madrid, Spain
Ana M. Pizarro: IMDEA Nanoscience, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain
Roberto Otero: IMDEA Nanoscience, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain
José M. Gallego: Instituto de Ciencia de Materiales de Madrid, c/ Sor Juana Inés de la Cruz 3, Cantoblanco, 28049 Madrid, Spain
Pablo Ballester: Institute of Chemical Research of Catalonia, Barcelona Institute of Science and Technology
José R. Galan-Mascaros: Institute of Chemical Research of Catalonia, Barcelona Institute of Science and Technology
David Ecija: IMDEA Nanoscience, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: Abstract On-surface synthesis is a promising strategy for engineering heteroatomic covalent nanoarchitectures with prospects in electronics, optoelectronics and photovoltaics. Here we report the thermal tunability of reaction pathways of a molecular precursor in order to select intramolecular versus intermolecular reactions, yielding monomeric or polymeric phthalocyanine derivatives, respectively. Deposition of tetra-aza-porphyrin species bearing ethyl termini on Au(111) held at room temperature results in a close-packed assembly. Upon annealing from room temperature to 275 °C, the molecular precursors undergo a series of covalent reactions via their ethyl termini, giving rise to phthalocyanine tapes. However, deposition of the tetra-aza-porphyrin derivatives on Au(111) held at 300 °C results in the formation and self-assembly of monomeric phthalocyanines. A systematic scanning tunnelling microscopy study of reaction intermediates, combined with density functional calculations, suggests a [2+2] cycloaddition as responsible for the initial linkage between molecular precursors, whereas the monomeric reaction is rationalized as an electrocyclic ring closure.

Date: 2016
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DOI: 10.1038/ncomms11002

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