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Synlett 2022; 33(08): 737-753
DOI: 10.1055/a-1740-7139
DOI: 10.1055/a-1740-7139
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Conjugated Nanohoops with Dibenzo[a,e]pentalenes as Nonalternant and Antiaromatic π-Systems
Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – project numbers 230408635, 434040413 and INST 40/467-1 FUGG.
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 complexesPublication History
Received: 20 December 2021
Accepted after revision: 14 January 2022
Accepted Manuscript online:
14 January 2022
Article published online:
17 March 2022
© 2022. Thieme. All rights reserved
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