American Chemical Society
jo801643u_si_003.cif (14.96 kB)

A Triphenylene-Based Triptycene with Large Free Volume Synthesized by Zirconium-Mediated Biphenylation

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posted on 2009-01-02, 00:00 authored by Cameron L. Hilton, Christopher R. Jamison, Hannah K. Zane, Benjamin T. King
Biphenylation using (Li(THF)4)2·Zr(biphe)3 of hexabromotriptycenes bearing H (1-H) or Bu (1-Bu) at the bridgeheads gave triptycenes with triphenylene blades. The blades extend both perpendicular and parallel to the 3-fold axis and generate a large intramolecular free volume (IMFV) (1-H, AM1, 710 Å3; cf. triptycene, AM1 71 Å3). Crystals of 1-H could not be obtained. Triptycene 1-Bu, in which the Bu groups fill the voids near the bridgehead, was crystalline. X-ray diffraction analysis revealed crystal packing with alternating, interlocked corrugated and distorted hexagonal layers.