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Journal of Chemical Crystallography

, Volume 42, Issue 2, pp 111–118 | Cite as

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

  • Mariolino Carta
  • Madeleine Helliwell
  • Neil B. McKeownEmail author
Original Paper

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

This paper describes the crystal structure of four spiro-bis(1,2,3,4-tetrahydronaphthalene)-based derivatives—that serve as precursors polymers of intrinsic microporosity and provide the important site of contortion within fused-ring structures.

Keywords

Microporous materials Polymers Spiro-compounds CH···π bonding 

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Mariolino Carta
    • 1
  • Madeleine Helliwell
    • 2
  • Neil B. McKeown
    • 1
    Email author
  1. 1.School of ChemistryCardiff UniversityCardiffUK
  2. 2.School of ChemistryUniversity of ManchesterManchesterUK

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