Issue 30, 2021

Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs

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[n]CPPs (n = 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[a,e]pentalene-based nanohoops DBP[n]CPPs with antiaromatic character and ambipolar electrochemical behavior. Due to their strained structures the DBP[n]CPPs do not racemize at room temperature, which is supported by high calculated isomerization barriers. X-ray crystallographic investigations on the DBP[n]CPPs and their precursors as well as DFT calculations provide insight into the build-up of strain energy during the synthetic transformations.

Graphical abstract: Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs

Supplementary files

Article information

Article type
Edge Article
Submitted
18 may 2021
Accepted
19 iyn 2021
First published
22 iyn 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 10150-10158

Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs

D. Wassy, M. Hermann, J. S. Wössner, L. Frédéric, G. Pieters and B. Esser, Chem. Sci., 2021, 12, 10150 DOI: 10.1039/D1SC02718B

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