Triptycene-Based Ladder Polymers with One-Handed Helical Geometry
Name
doi-10.1021 jacs.8b13865.pdf
Description
Accepted version
Size
6.56 MB
Format
Adobe PDF
Checksum (MD5)
ccdda32a4ab8f6201679abbece460ce3
Author(s)
Ikai, Tomoyuki
Yoshida, Takumu
Shinohara, Ken-ichi
Taniguchi, Tsuyoshi
Wada, Yuya
Swager, Timothy M
Date Issued
February 2019
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Ikai, Tomoyuki et al. "Triptycene-Based Ladder Polymers with One-Handed Helical Geometry." Journal of the American Chemical Society 141, 11 (February 2019): 4696–4703 © 2019 American Chemical Society
Version
Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jacs.8b13865
