Conjugated Nanohoops with Dibenzo[a,e]pentalenes as Nonalternant and Antiaromatic π-Systems

Abstract

Conjugated nanohoops are excellent as candidates for studying structure–property relationships, as optoelectronic materials, and as hosts for supramolecular chemistry. Whereas carbon nanohoops containing aromatics have been well studied, antiaromatic units had not been incorporated until our group recently did so, using dibenzo[a,e]pentalene (DBP). The nonalternant electronic character of the DBP units significantly influences the optoelectronic properties of such nanohoops. Here, we summarize our synthetic strategies toward DBP-containing nanohoops, together with their structural and electronic properties, chirality, and host–guest chemistry. We demonstrate how incorporating antiaromatic units leads to unique properties and opens new synthetic avenues, making such nanohoops attractive as potential electronic materials.

1 Introduction

2 Synthesis

3 Structural Properties

4 Electronic Properties

5 Chirality

6 Host–Guest Chemistry

Key words

nanohoops - antiaromaticity - ambipolar materials - chiroptical properties - cycloparaphenylenes - fullerene complexes

Publication History

Received: 20 December 2021

Accepted after revision: 14 January 2022

Accepted Manuscript online:
14 January 2022

Article published online:
17 March 2022

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