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Crystal Structures of 5,6,5′,6′-Tetramethoxy-1,1′-spirobisindane-3,3′-dione and two of its Fluorene Adducts

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Abstract

The structures of three spirobisindanes 1, 2a and 2b are reported. Each compound is a precursor to a Polymers of Intrinsic Microporosity (PIM) and is the component that provides the necessary site of contortion within the polymer. Of particular importance are the angles formed between the aromatic units around the spiro-centre as it may have direct relevance to the inefficiency of packing in the solid state packing, we think, induces microporosity in the final polymer. Compound 1 crystallized in the monoclinic P21/c space group with unit cell parameters a = 9.8000(5) Ǻ, b = 17.8710(9) Ǻ, c = 10.4100(5) Ǻ, β = 106.6280(10)°, V = 1746.92(15) A3, Z = 4, D = 1.401 Mg/m3. Compound 2a crystallized in the monoclinic P21/c space group with unit cell parameters a = 9.7460(13) Ǻ, b = 30.291(4) Ǻ, c = 8.6740(12) Ǻ, β = 97.111(3)°, 2541.0(6) A3, Z = 4, D = 1.319 Mg/m3. Compound 2b crystallized in the monoclinic P21/n space group with unit cell parameters a = 13.5670(9) Ǻ, b = 12.7930(8) Ǻ, c = 22.1960(14) Ǻ, β = 96.6630(10)°, V = 3826.4(4) A3, Z = 4, D = 1.265 Mg/m3.

Graphical Abstract

This paper describes the crystal structure of three spirobisindanes-based derivatives that serve as precursors Polymers of Intrinsic Microporosity and provide the important site of contortion within fused-ring structures.

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Authors and Affiliations

  1. School of Chemistry, Cardiff University, Cardiff, CF10 3AT, UK

    Mariolino Carta & Neil B. McKeown

  2. Department of Chemistry, University of Manchester, Manchester, M13 9PL, UK

    James Raftery

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  1. Mariolino Carta
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  2. James Raftery
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  3. Neil B. McKeown
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Correspondence to Neil B. McKeown.

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Carta, M., Raftery, J. & McKeown, N.B. Crystal Structures of 5,6,5′,6′-Tetramethoxy-1,1′-spirobisindane-3,3′-dione and two of its Fluorene Adducts. J Chem Crystallogr 41, 98–104 (2011). https://doi.org/10.1007/s10870-010-9844-1

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  • DOI: https://doi.org/10.1007/s10870-010-9844-1

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