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A π-expanded helicene, that is the helically twisted analogue of kekulene, was synthesized using a 6-fold ring-closing olefin metathesis (RCM) reaction as a key step. The π-expanded geometry with large helical diameter ( d = 10.2 Å), consisting only of carbon and hydrogen atoms (CH), was unambiguously determined by single-crystal X-ray analysis. We found that the π-expanded helicene with large helical diameter will act as a soft molecular spring with a small spring constant. Interestingly, the mechanical properties of molecular springs roughly satisfied a physical formula for macroscopic spring materials, i.e., the force constant of the elongation of molecular spring ( k) is inversely proportional to the third power of the helical diameter.
This article was published in the following journal.
Name: Journal of the American Chemical Society
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