Abstract
AbstractPorphyrin nanotapes (Por NTs) are promising structures for their use as molecular wires thanks to a high degree of π‐conjugation, low HOMO—LUMO gaps, and exceptional conductance. Such structures have been prepared in solution, but their on‐surface synthesis remains unreported. Here, meso–meso triply fused Por NTs have been prepared through a two‐step synthesis on Au(111). The diradical character of the on‐surface formed building block PorA2, a phenalenyl π‐extended ZnIIPor, facilitates intermolecular homocoupling and allows for the formation of laterally π‐extended tapes. The structural and electronic properties of individual Por NTs are addressed, both on Au(111) and on a thin insulating NaCl layer, by high‐resolution scanning probe microscopy/spectroscopy complemented by DFT calculations. These Por NTs carry one unpaired electron at each end, which leads to magnetic end states. Our study provides a versatile route towards Por NTs and the atomic‐scale characterization of such tapes.
Highlights
Tetrapyrroles, “the pigments of life”, are key molecules for the metabolism of living organisms, supporting functions of vital importance such as electron transport, light-harvesting and oxygen reduction
The synthetic route employed for the fabrication of surface-supported laterally p-extended Porphyrin nanotapes (Por NTs) starts with Por(dmp)2 which was synthesized in few steps by solution chemistry.[22]
PorA2 exhibits a diradical open-shell character with two unpaired electrons delocalized over the Por longer “edges”
Summary
Tetrapyrroles, “the pigments of life”, are key molecules for the metabolism of living organisms, supporting functions of vital importance such as electron transport, light-harvesting and oxygen reduction Within this family of compounds, porphyrins (Pors) are of particular interest thanks to their planar structure with an aromatic core of 18 p-electrons, remarkable thermal stability, tunable redox properties, and intense optical features.[1] Taking advantage of these properties and the Pors extraordinary chemical versatility, these macrocycles have been tailored for their use in a wide range of fields, such as photovoltaics,[2] catalysis[3] and molecular electronics,[4] to mention a few. Angewandte Chemie International Edition published by Wiley-VCH GmbH The fabricated Por NTs feature magnetic end states resulting from the presence of an unpaired electron at each end of the Au(111)-supported NTs
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