Issue 29, 2023

Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: “one-pot” synthesis and chiral resolution

Abstract

Twisted polyarenes with persistent chirality are desirable but their synthesis has remained a challenge. In this study, we present a “one-pot” synthesis of 1,2:8,9-dibenzozethrene (DBZ) and its vertically fused dimers and trimers using nickel-catalyzed cyclo-oligomerization reactions. X-ray crystallographic analysis confirmed highly twisted helical structures that consist of equal parts left- and right-handed enantiomers. Notably, the end-to-end twist between the terminal anthracene units measured 66°, 130°, and 201° for the DBZ monomer, dimer, and trimer, respectively, setting a new record among twisted polyarenes. Furthermore, the chiral resolution by HPLC yielded two enantiomers for the fused DBZ dimer and trimer, both of which maintained stable configurations and showed absorption dissymmetry factors of around 0.008–0.009. Additionally, their optical and electrochemical properties were investigated, which exhibited a chain-length dependence.

Graphical abstract: Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: “one-pot” synthesis and chiral resolution

Supplementary files

Article information

Article type
Edge Article
Submitted
04 May 2023
Accepted
19 Jun 2023
First published
23 Jun 2023
This article is Open Access

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

Chem. Sci., 2023,14, 7922-7927

Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: “one-pot” synthesis and chiral resolution

Z. Sun, W. Fan, Y. Han, W. Yuan, Y. Ni, J. Wang, H. Wei, Y. Zhao, Z. Sun and J. Wu, Chem. Sci., 2023, 14, 7922 DOI: 10.1039/D3SC02285D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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