Synthesis and Properties of Conjugated Nanohoops Incorporating Dibenzo[ a, e]pentalenes: [2]DBP[12]CPPs

Daniel Wassy; Manuel Pfeifer; Birgit Esser

doi:10.1021/acs.joc.9b01195

Synthesis and Properties of Conjugated Nanohoops Incorporating Dibenzo[ a, e]pentalenes: [2]DBP[12]CPPs

J Org Chem. 2020 Jan 3;85(1):34-43. doi: 10.1021/acs.joc.9b01195. Epub 2019 Jun 25.

Authors

Daniel Wassy¹, Manuel Pfeifer¹, Birgit Esser^{1

2

3}

Affiliations

¹ Institute for Organic Chemistry , University of Freiburg , Albertstraße 21 , 79104 Freiburg , Germany.
² Freiburg Materials Research Center , University of Freiburg , Stefan-Meier-Straße 21 , 79104 Freiburg , Germany.
³ Cluster of Excellence livMatS @ FIT - Freiburg Center for Interactive Materials and Bioinspired Technologies , University of Freiburg , Georges-Köhler-Allee 105 , 79110 Freiburg , Germany.

PMID: 31187987
DOI: 10.1021/acs.joc.9b01195

Abstract

Conjugated nanohoops allow studying the effect of cyclic conjugation and bending on the incorporated π-systems. To date, no such system containing antiaromatic units has been reported. We herein present [12]cycloparaphenylenes incorporating two dibenzo[a,e]pentalene units: [2]DBP[12]CPP nanohoops. Dibenzo[a,e]pentalene is a nonalternant hydrocarbon with antiaromatic character. The syntheses and optoelectronic properties of two different [2]DBP[12]CPP nanohoops with electronically modifying substituents are reported, accompanied by TDDFT calculations.