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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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Contributed by Steven BacharachReposted from Computational Organic Chemistry with permissionI have recently been interested in curved aromatic systems see my own paper on double helicenes.1 In this post, I cover four recent papers that discuss non-planar...
I have recently been interested in curved aromatic systems see my own paper on double helicenes.1 In this post, I cover four recent papers that discuss non-planar aromatic molecules.The first paper2 discusses the warped aromatic 1 built off of the scaffold...