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A hindered subphthalocyanine that forms crystals with included aromatic solvent but will not play ball with C60

Burt, Luke A., Bezzu, Caterina Grazia, McMonagle, Charlie J., Moggach, Stephen A. and McKeown, Neil B. 2016. A hindered subphthalocyanine that forms crystals with included aromatic solvent but will not play ball with C60. Journal of Porphyrins and Phthalocyanines 20 (08n11) , pp. 1034-1040. 10.1142/S1088424616500528

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Abstract

A novel subphthalocyanine containing bulky substituents placed at its peripheral sites (i.e. 2,3,9,10,16,17-hexa(2′,6′-di-iso-propylphenoxy)boron subphthalocyanine) was prepared and assessed for supramolecular binding with C60, through crystallisation and fluorescence studies. Three different crystal polymorphs of the subphthalocyanine were obtained that showed inclusion of a single aromatic solvent molecule within the well-defined cavity of the molecule but complete exclusion of C60. Analysis of the crystal structures indicated that the bowl-shaped cavity of the subphthalocyanine molecule was only accessible to small molecules due to the steric congestion surrounding the macrocycle, which results in hindered rotation of the substituents on the NMR timescale. Enhanced solubility, up to 42.0 g/L in common organic solvents, was demonstrated consistent with the crystal structures which are dominated by relatively weak intermolecular interactions, which allow solvent molecules to play a role in crystallisation.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: WorldSciNet
ISSN: 1088-4246
Date of Acceptance: 5 February 2016
Last Modified: 04 Jun 2019 10:40
URI: http://orca.cf.ac.uk/id/eprint/123152

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