Triptycene-Based Ladder Polymers with One-Handed Helical Geometry
Autor: | Takumu Yoshida, Tsuyoshi Taniguchi, Yuya Wada, Timothy M. Swager, Ken-ichi Shinohara, Tomoyuki Ikai |
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Rok vydání: | 2019 |
Předmět: |
chemistry.chemical_classification
Steric effects Anthracene Regioselectivity Geometry General Chemistry Polymer 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry chemistry Chain (algebraic topology) Phenylene Triptycene Molecule |
Zdroj: | Journal of the American Chemical Society. 141(11) |
ISSN: | 1520-5126 |
Popis: | 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. |
Databáze: | OpenAIRE |
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