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Issue 4, 2010
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Supramolecular networks of a H-shaped aromatic phenol host

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Abstract

X-Ray crystal structures of 1,4-di[bis(hydroxyphenyl)methyl]benzene and its solvates and cocrystals were analyzed for the occurrence of network architectures. From the simplest 1D ladder in EtOAc, DMSO and i-PrOH solvates of 1 (R1 = R2 = R4 = H, R3 = OH), doubly-interpenetrated 1D ladders in its guest-free form and 1D/2D-interpenetrated ladder networks in a cocrystal with phenazine were identified. The dioxane and DMSO solvates of 2 (R1 = R3 = OMe, R2 = OH, R4 = H), and the DMSO and toluene solvates of 4 (R1 = H, R2 = R4 = Me, R3 = OH) also adopt 1D ladder networks. Monomethyl phenol 3 (R1 = R2 = H, R3 = OH, R4 = Me) makes 2D grids of ladders that include nitromethane solvent in the channels. The hexagonal (6,3) net in the cocrystal of 1 with pyrazine-N,N′-dioxide is triply-interpenetrated in a 2D architecture. The DMF solvate of 3 is similar to 1·(PyzNO)2, except that the (6,3) nets are doubly-interpenetrated via Hopf links. An orthorhombic nitromethane solvate of 1 is 2D → 3D polycatenated with a degree of catenation (DOC) = 2/2, whereas the monoclinic polymorph of 1·(CH3NO2)2, as well as the chloroform inclusion structure of 4, adopt the rare (5,34) pentagonal net. Platonic (6,3) and Catalan (5,34) nets in the broader category of a uniform network topology were realized from H-shaped molecules 1–4 in different solvent inclusion and cocrystal structures. Finally, a cocrystal of 1 with quinoxaline forms a polyrotaxane 1D → 1D chain of Euclidean entanglement. Polythreaded rotaxane, pentagonal Catalan and 1D/2D interpenetrated nets are, as such, rare in organic molecular crystals. The role of the solvent/co-former in affording diverse supramolecular networks and entanglement modes are rationalized in the crystal structures.

Graphical abstract: Supramolecular networks of a H-shaped aromatic phenol host

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Publication details

The article was received on 02 Jun 2009, accepted on 05 Oct 2009 and first published on 23 Nov 2009


Article type: Paper
DOI: 10.1039/B9NJ00234K
Citation: New J. Chem., 2010,34, 623-636
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    Supramolecular networks of a H-shaped aromatic phenol host

    R. Thakuria, B. Sarma and A. Nangia, New J. Chem., 2010, 34, 623
    DOI: 10.1039/B9NJ00234K

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