A Supramolecular Polymer Constituted of Antiaromatic NiII Norcorroles

Angew Chem Int Ed Engl. 2022 Feb 1;61(6):e202114230. doi: 10.1002/anie.202114230. Epub 2021 Dec 21.

Abstract

For the creation of next-generation organic electronic materials, the integration of π-systems has recently become a central theme. Such functional materials can be assembled by supramolecular polymerization when aromatic π-systems are used as monomers, and the properties of the resulting supramolecular polymer strongly depend on the electronic structure of the monomers. Here, we demonstrate the construction of a supramolecular polymer consisting of an antiaromatic π-system as the monomer. An amide-functionalized NiII norcorrole derivative formed a one-dimensional supramolecular polymer through π-π stacking and hydrogen-bonding interactions, ensuring the persistency of the conducting pathway against thermal perturbation, which results in higher charge mobility along the tightly bound linear aggregates than that of the aromatic analogue composed of ZnII porphyrins.

Keywords: antiaromaticity; hydrogen bond; norcorrole; supramolecular polymer; π-π stacking.