title: On-surface generation and imaging of arynes by atomic force microscopy.
abstract: Reactive intermediates are involved in many chemical transformations. However, their characterization is a great challenge because of their short lifetimes and high reactivities. Arynes, formally derived from arenes by the removal of two hydrogen atoms from adjacent carbon atoms, are prominent reactive intermediates that have been hypothesized for more than a century. Their rich chemistry enables a widespread use in synthetic chemistry, as they are advantageous building blocks for the construction of polycyclic compounds that contain aromatic rings. Here, we demonstrate the generation and characterization of individual polycyclic aryne molecules on an ultrathin insulating film by means of low-temperature scanning tunnelling microscopy and atomic force microscopy. Bond-order analysis suggests that a cumulene resonance structure is the dominant one, and the aryne reactivity is preserved at cryogenic temperatures. Our results provide important insights into the chemistry of these elusive intermediates and their potential application in the field of on-surface synthesis.
authors.affiliation: IBM Research-Zurich, 8803 Rüschlikon, Switzerland.
authors.forename: Niko
authors.identifier: 0000000339894454
authors.initials: N
authors.lastname: Pavliček
authors.affiliation: IBM Research-Zurich, 8803 Rüschlikon, Switzerland.
authors.forename: Bruno
authors.initials: B
authors.lastname: Schuler
authors.affiliation: Centro de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela. Santiago de Compostela 15782, Spain.
authors.forename: Sara
authors.initials: S
authors.lastname: Collazos
authors.affiliation: IBM Research-Zurich, 8803 Rüschlikon, Switzerland.
authors.forename: Nikolaj
authors.initials: N
authors.lastname: Moll
authors.affiliation: Centro de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela. Santiago de Compostela 15782, Spain.
authors.forename: Dolores
authors.initials: D
authors.lastname: Pérez
authors.affiliation: Centro de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela. Santiago de Compostela 15782, Spain.
authors.forename: Enrique
authors.initials: E
authors.lastname: Guitián
authors.affiliation: IBM Research-Zurich, 8803 Rüschlikon, Switzerland.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Meyer
authors.affiliation: Centro de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela. Santiago de Compostela 15782, Spain.
authors.forename: Diego
authors.initials: D
authors.lastname: Peña
authors.affiliation: IBM Research-Zurich, 8803 Rüschlikon, Switzerland.
authors.forename: Leo
authors.initials: L
authors.lastname: Gross