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Synfacts 2011(8): 0847-0847  
DOI: 10.1055/s-0030-1260700
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

It’s all about the Twist!

Contributor(s): Timothy M. Swager, Jason R. Cox
K. Maeda, H. Mochizuki, K. Osato, E. Yashima*
Nagoya University, Japan
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

The authors report the syntheses of two new polyacetylenes bearing pendant β-cyclodextrin groups linked via ether or ester linkages. The resulting high molecular weight polymers spontaneously form helical structures that can be modulated by addition of external stimuli. Poly-2β undergoes enantioselective gelation when treated with an excess of (S)-PEA. Interestingly, poly-3β does not exhibit this behavior, leading the authors to surmise that the enantioselectivity is related to the presence of Lewis basic ester linkages rather than an inclusion complex.