Triptycene-Based Ladder Polymers with One-Handed Helical Geometry

Journal of the American Chemical Society
Tomoyuki IkaiTimothy M Swager

Abstract

Here we report an efficient synthesis of optically active ladder-type molecules and polymers through intramolecular cyclization of chiral triptycenes containing bis[2-(4-alkoxyphenyl)ethynyl]phenylene units. The electrophile-induced cyclization reactions are directed away from the bridgehead carbon atoms of triptycene by steric factors, thereby producing one-handed twisted ladder units without any detectable byproducts. Moreover, the quantitative and regioselective nature of this intramolecular cyclization allowed us to synthesize optically active ladder polymers with a well-defined one-handed helical geometry in which homoconjugated dibenzo[ a, h]anthracene units are helically arranged along the main chain. This synthesis route enables the construction of a variety of nanoscale helical ladder architectures and provides an entry into new chiroptical materials.

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Citations

Jun 18, 2020·ChemistryOpen·Giovanni PredaDario Pasini
Sep 5, 2019·Chemical Communications : Chem Comm·Yuya WadaTomoyuki Ikai
Jul 11, 2020·Chemistry : a European Journal·Xubin WangMichael Mastalerz
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Jan 13, 2021·Chemistry : a European Journal·Md Nasim Khan, Thomas Wirth
Nov 5, 2020·The Journal of Organic Chemistry·Kevin BaumgärtnerMichael Mastalerz
Dec 24, 2019·Journal of the American Chemical Society·Yuji NishiiMasahiro Miura

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