A hindered subphthalocyanine that forms crystals with included aromatic solvent but will not play ball with C-60

Luke A. Burt, C. Grazia Bezzu, Charlie J. McMonagle, Stephen A. Moggach, Neil B. McKeown

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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 C-60, 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 C-60. 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.

Original languageEnglish
Pages (from-to)1034-1040
Number of pages7
JournalJournal of Porphyrins and Phthalocyanines
Volume20
Issue number8-11
DOIs
Publication statusPublished - 2016
Externally publishedYes

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