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Crystal Structures of a Series of 1,1-Spiro-bis(1,2,3,4-tetrahydronaphthalene)-Based Derivatives

Research paper by Mariolino Carta, Madeleine Helliwell, Neil B. McKeown

Indexed on: 27 Nov '11Published on: 27 Nov '11Published in: Journal of chemical crystallography



Abstract

The structures of four spirobisnaphthalenes based monomers 1, 2, 3a and 3b are reported. Each compound represents a methoxylated precursor which after deprotection led to the formation of a monomer successfully used for the synthesis of Polymers of intrinsic microporosity. The spiro-centre represents the site of contortion that, since its rigidity, leads to inefficient packing in the solid state inducing microporosity in the final polymer. Compound 1 crystallized in the monoclinic P2/c space group with unit cell parameters a = 8.1659(19) Å, b = 7.5298(18) Å, c = 19.130(5) Å, β = 97.935(4)°, V = 1165.0(5) Å3, Z = 2, D = 1.210 Mg m−3. Compound 2 crystallized in the monoclinic P21/n space group with unit cell parameters a = 12.6940(9) Å, b = 7.7267(6) Å, c = 19.9754(15) Å, β = 97.220(1)°, V = 1943.7(3) Å3, Z = 4, D = 1.355 Mg m−3. Compound 3a crystallized in the monoclinic P21/c space group with unit cell parameters a = 16.8137(14) Å, b = 10.5577(9) Å, c = 31.344(3) Å, β = 103.618(1)°, V = 5407.5(8) Å3, Z = 8, D = 1.308 Mg m−3. Compound 3b crystallized in the monoclinic Pc space group with unit cell parameters a = 15.594 Å, b = 12.564 Å, c = 18.339 Å, β = 90.224(1)°, V = 3593.0 Å3, Z = 4, D = 1.236 Mg m−3.

Graphical abstract 10.1007/s10870-011-0211-7.gif