On-surface synthesis of organocopper metallacycles through activation of inner diacetylene moieties

Cirera, Borja; Riss, Alexander; Mutombo, Pingo; Urgel, José I.; Santos, José; Di Giovannantonio, Marco; Widmer, Roland; Stolz, Samuel; Sun, Qiang; Bommert, Max; Fasel, Roman; Jelínek, Pavel; Auwärter, Willi; Martín, Nazario; Écija, David (2021). On-surface synthesis of organocopper metallacycles through activation of inner diacetylene moieties. Chemical Science, 12(38), pp. 12806-12811. The Royal Society of Chemistry 10.1039/D1SC03703J

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The design of organometallic complexes is at the heart of modern organic chemistry and catalysis. Recently, on-surface synthesis has emerged as a disruptive paradigm to design previously precluded compounds and nanomaterials. Despite these advances, the field of organometallic chemistry on surfaces is still at its infancy. Here, we introduce a protocol to activate the inner diacetylene moieties from a molecular precursor by copper surface adatoms affording the formation of unprecedented organocopper metallacycles on Cu(111). The chemical structure of the resulting complexes is characterized by scanning probe microscopy and x-ray photoelectron spectroscopy, being complemented by density functional calculations and scanning probe microscopy simulations. Our results pave avenues to the engineering of organometallic compounds and steer the development of polyyne chemistry on surfaces.

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