Fluctuating Carbonaceous Networks with a Persistent Molecular Shape: A Saddle-Shaped Geodesic Framework of 1,3,5-Trisubstituted Benzene (Phenine)

Angewandte Chemie
Koki IkemotoHiroyuki Isobe

Abstract

A saddle-shaped macromolecule has been synthesized. The molecule was designed as a geodesic saddle with 1,3,5-trisubstituted benzene (named phenine) as the fundamental unit. The phenines were woven into a polygonal framework that was composed of 168 sp2 -hybridized carbon atoms. The saddle-shaped structure with unique symmetry showed atypical conformational changes. The biaryl linkages in this molecule had a small energy barrier for rotation, and these structural fluctuations resulted in seven 1 H NMR resonances representing 84 aromatic hydrogen atoms. Nevertheless, the overall saddle shape of the molecule was persistent, and the "up" and "down" orientations of phenine moieties circulated to give average 1 H resonances. The structural characteristics of this molecule, including the anomalous entropy-driven dimerization, may deepen our understanding of defect-rich graphitic sheets.

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Citations

Jul 15, 2018·Angewandte Chemie·Marcin A Majewski, Marcin Stępień
Jul 22, 2019·Angewandte Chemie·Yu-Min LiuYuan-Zhi Tan
Nov 30, 2019·Chemistry, an Asian Journal·Taisuke MatsunoHiroyuki Isobe
Apr 15, 2020·Nature Communications·Koki IkemotoHiroyuki Isobe
Mar 5, 2020·Chemistry, an Asian Journal·Tatsuru MioHiroyuki Isobe
Jan 12, 2019·Science·Zhe SunHiroyuki Isobe
Oct 26, 2018·Organic Letters·Xuejin YangQian Miao
Dec 15, 2018·The Journal of Organic Chemistry·Wai-Shing WongHak-Fun Chow

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