Abstract
The synthesis, characterization, and crystal structures of two novel strained cyclic diacetylenes are reported. A discussion is presented about the relative bond distances of the diacetylenes compared to a previously reported strained cyclic diacetylene to further determine the degree of aromaticity of that compound. 1,2:5,6:9,10:13,14-Tetrabenzo-3,7,11,15,17-pentadehydro[18] annulene (5) is triclinic, P −1, with α = 9.489(5), b = 10.550(5), c = 12.155(6) Å, α = 100.50(4), β = 106.50(4), γ = 100.85(4)°. 1,2:5,6:9,10:13,14:17,18-Pentabenzo-3,7,11,15,19,23,25-heptadehydro[26]annulene (7) is triclinic, P −1, with a = 9.611(2), b = 10.388(3), c = 15.963(3) Å, α = 88.67(2), β = 76.25(1), γ = 68.69(2). In addition, two precursors of 5, 3 and 4 which have a helical twist, are reported. [1,2-ethynediyl-bis(2,1-phenylene-2,1-ethynediyl-2,1-phenylene-2,1-ethynediyl]bis[trimethyl-silane] (3) is monoclinic, P21/c, with a = 13.682(4), b = 9.787(2), c = 13.448(4) Å, β = 112.37(2)°. 1,1′-(1,2-ethynyldiyl)bis[2-[(2-ethynylphenyl)ethynyl]-benzene (4) is monoclinic, P21/n, with a = 15.951(3), b = 3.999(1), c = 18.168(4) Å, β = 99.05(3)°.
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Baldwin, K.P., Simons, R.S., Scheiman, D.A. et al. Synthesis, characterization, and crystal structures of two strained cyclic diacetylenes and their precursors. Journal of Chemical Crystallography 28, 353–360 (1998). https://doi.org/10.1023/A:1022408107946
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DOI: https://doi.org/10.1023/A:1022408107946