17051-14-8Relevant articles and documents
Preparation of substituted triphenylenesvianickel-mediated Yamamoto coupling
LeDrew, Joshua,Maly, Kenneth E.,Schroeder, Zachary W.,Selmani, Vanessa M.
, p. 39564 - 39569 (2021/12/24)
Substituted triphenylenes show promise as organic semiconductors because of their ability to form columnar liquid crystalline phases featuring extended π-stacked arrays. While there are several methods for preparing triphenylenes, including oxidative cyclization reactions such as the Scholl reaction, as well as transition metal-catalyzed aryne cyclotrimerization, these methods are not effective for electron deficient triphenylenes. Here we demonstrate that the nickel-mediated Yamamoto coupling ofo-dibromoarenes is a concise and efficient way to prepare substituted triphenylenes, including electron-deficient systems that are otherwise challenging to prepare. We also demonstrate the application of this approach to prepare electron deficient discotic mesogens composed of triphenylenes bearing imide and thioimide groups.
THE CRYSTAL AND MOLECULAR STRUCTURE OF OCTAFLUOROBIPHENYLENE, C12F8
Jones, J. Bowen,Brown, D. S.,Massey, A. G.,Slater, P. J.
, p. 75 - 88 (2007/10/02)
Octafluorobiphenylene was made by heating 1,2-diiodotetrafluorobenzene in a sealed, evacuated tube with either copper, lead or bismuth.The crystal used for the diffraction studies was grown from hexane.Crystal data: C12F8, Mr = 296.116, monoclinic, A2/a, a = 21.140(2), b = 6.430(6), c = 36.340(3) Angstroem, β = 123.76(3)deg, U = 4106.73 Angstroem3, Z = 16, Dm = 1.884 g cm-3, DX = 1.907 g cm-3, λ(CuKα) = 1.5418 Angstroem, μ =1.810 mm-1, F(OOO) = 2304, measurement temperature = 293K, R = 0.059 for 2230 reflections with I > 3?(I).
