Enantiopure Nanohoops Through Racemic Resolution of Diketo[]CPPs by Chiral Derivatization As Precursors to DBP[]CPPs

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Aug 11

PMID 34377404

Citations 4

Authors

Daniel Wassy

Mathias Hermann

Jan S Wossner

Lucas Frederic

Gregory Pieters

Birgit Esser

Affiliations

Soon will be listed here.

Abstract

Strained conjugated nanohoops are attractive synthetic targets due to the bending of their π-system, which leads to intriguing optoelectronic properties, among others. By incorporating non-mirror-symmetric aromatic panels, chiral nanohoops can be obtained. We herein present a strategy to enantiopure nanohoops by racemic resolution through chiral derivatization of diketone-embedded hoops. The resulting diketo[]CPPs ( = 6, 7) contain two stereogenic carbon atoms each and possess high fluorescence quantum yields paired with circularly polarized luminescence. These are versatile precursors to chiral dibenzo[,]pentalene-based nanohoops DBP[]CPPs with antiaromatic character and ambipolar electrochemical behavior. Due to their strained structures the DBP[]CPPs do not racemize at room temperature, which is supported by high calculated isomerization barriers. X-ray crystallographic investigations on the DBP[]CPPs and their precursors as well as DFT calculations provide insight into the build-up of strain energy during the synthetic transformations.

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