6533b85ffe1ef96bd12c1278

RESEARCH PRODUCT

On-Surface Synthesis of Antiaromatic and Open-Shell Indeno[2,1- b ]fluorene Polymers and Their Lateral Fusion into Porous Ribbons

Carlo A. PignedoliAliaksandr V. YakutovichKristjan EimreQiang ChenPascal RuffieuxJosé I. UrgelKlaus MüllenKlaus MüllenAkimitsu NaritaAkimitsu NaritaShantanu MishraMarco Di GiovannantonioRoman FaselRoman Fasel

subject

Materials science530 PhysicsBand gapFOS: Physical sciencesConjugated systemFluorene010402 general chemistry01 natural sciencesBiochemistryCatalysislaw.inventionchemistry.chemical_compoundColloid and Surface Chemistrylaw540 ChemistryOrganic electronicsCondensed Matter - Materials ScienceSpintronicsMaterials Science (cond-mat.mtrl-sci)General Chemistry0104 chemical sciencesUnpaired electronchemistryChemical physicsScanning tunneling microscopeAntiaromaticity

description

Polycyclic hydrocarbons have received great attention due to their potential role in organic electronics and, for open-shell systems with unpaired electron densities, in spintronics and da-ta storage. However, the intrinsic instability of polyradical hydrocarbons severely limits de-tailed investigations of their electronic structure. Here, we report the on-surface synthesis of conjugated polymers consisting of indeno[2,1-b]fluorene units, which are antiaromatic and open-shell biradicaloids. The observed reaction products, which also include a non-benzenoid porous ribbon arising from lateral fusion of unprotected indeno[2,1-b]fluorene chains, have been characterized via low temperature scanning tunneling microscopy/spectroscopy and non-contact atomic force microscopy, complemented by density-functional theory calculations. These polymers present a low band gap when adsorbed on Au(111). Moreover, their pro-nounced antiaromaticity and radical character, elucidated by ab initio calculations, make them promising candidates for applications in electronics and spintronics. Further, they provide a rich playground to explore magnetism in low-dimensional organic nanomaterials.

10.1021/jacs.9b05335http://dx.doi.org/10.1021/jacs.9b05335