![]() ![]() Adsorption geometry determination of single molecules by atomic force microscopy. Local electronic and chemical structure of oligo-acetylene derivatives formed through radical cyclizations at a surface. The chemical structure of a molecule resolved by atomic force microscopy. Gross, L., Mohn, F., Moll, N., Liljeroth, P. On-surface activation of trimethylsilyl-terminated alkynes on coinage metal surfaces. Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111). Polycyclic aromatic chains on metals and insulating layers by repetitive cycloadditions. Effect of central π-system in silylated-tetraynes on σ-bond metathesis on surfaces. The on-surface synthesis of imine-based covalent organic frameworks with non-aromatic linkage. On-surface synthesis of 2D porphyrin-based covalent organic frameworks using terminal alkynes. Exploration of interfacial porphine coupling schemes and hybrid systems by bond-resolved scanning probe microscopy. Bottom-up fabrication and atomic-scale characterization of triply linked, laterally π-extended porphyrin nanotapes. Surface-assisted dehydrogenative homocoupling of porphine molecules. Organisation and ordering of 1D porphyrin polymers synthesised by on-surface Glaser coupling. On-surface synthesis of one-dimensional coordination polymers with tailored magnetic anisotropy. Nano-architectures by covalent assembly of molecular building blocks. Imaging single-molecule reaction intermediates stabilized by surface dissipation and entropy. Controlling a chemical coupling reaction on a surface: tools and strategies for on-surface synthesis. Atomically precise bottom-up fabrication of graphene nanoribbons. Molecular structure elucidation with charge-state control. On-surface synthesis and intermolecular cycloadditions of indacenoditetracenes, antiaromatic analogues of undecacene. ![]() Zuzak, R., Stoica, O., Blieck, R., Echavarren, A. Competing annulene and radialene structures in a single anti-aromatic molecule studied by high-resolution atomic force microscopy. On-surface synthesis of antiaromatic and open-shell indenofluorene polymers and their lateral fusion into porous ribbons. Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces. Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling. Synthesis and characterization of triangulene. Classic highlights in porphyrin and porphyrinoid total synthesis and biosynthesis. The breaking and mending of meso-tetraarylporphyrins: transmuting the pyrrolic building blocks. in Porphyrins and Metalloporphyrins (ed Smith, K. High resolution NMR spectra of porphin and of porphin derivatives. From small carbocyclic rings to porphyrins: a personal account of 50 years of research. Description of aromaticity in porphyrinoids. The porphyrins from the ‘annulene chemist’s’ perspective. Quantentheoretische Beiträge zum Benzolproblem. Glossary of terms used in theoretical organic chemistry. Aromaticity: a theoretical concept of immense practical importance. These insights are helpful to understand, and in turn design, reactions with aromatic species in on-surface chemistry and heterogeneous catalysis. The results are corroborated by density functional theory calculations, which show a direct correlation between aromaticity and thermodynamic stability of the reaction products. Our experiments show a substantially lower reactivity of carbon atoms that are stabilized by the aromatic diazaannulene pathway of free-base porphyrins. We examine and quantify the regioselectivity in the reactions by scanning tunnelling microscopy and bond-resolved atomic force microscopy at the single-molecule level. Here we investigate how aromaticity affects the reactivity of alkyne-substituted porphyrin molecules in cyclization and coupling reactions on a Au(111) surface. However, its role remains largely unexplored in on-surface chemistry, where the interaction with the substrate can alter the electronic and geometric structure of the adsorbates. Aromaticity is an established and widely used concept for the prediction of the reactivity of organic molecules.
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