A triphenylene-based triptycene with large free volume synthesized by zirconium-mediated biphenylation.
Biphenylation using (Li(THF)(4))(2) x 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 A(3); cf. triptycene, AM1 71 A(3)). 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.
Hilton
Cameron L
CL
Department of Chemistry, University of Nevada, Reno, Nevada 89557-0216, USA.
Jamison
Christopher R
CR
Zane
Hannah K
HK
King
Benjamin T
BT
D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D002911:Chrysenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D000873:Anthracenes; D002911:Chrysenes; D009942:Organometallic Compounds; C009590:triphenylene; D015040:Zirconium; C520712:triptycene