Abstract
Four Organic Molecules of Intrinsic Microporosity (OMIMs) were prepared by fusing triptycene-based components to a biphenyl core. Due to their rigid molecular structures that cannot pack space efficiently, these OMIMs form amorphous materials with significant microporosity as demonstrated by apparent BET surface areas in the range of 515–702 m2 g–1. Bulky cyclic 1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′-tetramethylbenzo units placed on the triptycene termini are especially efficient at enhancing microporosity.
Highlights
A recent report describes the exclusive synthesis of a naphthobenzobarrelene adduct by blocking addition across the central ring by placing bulky ferrocenyl groups at the 9,10 positions of anthracene and using the sterically crowded 3-trifluoromethylbenzyne as a coreactant.12e previous studies of benzyne addition to 2,3,5,6tetramethylanthracene reported naphthobenzobarrelene byproducts, and in the case of anthracene 3, it appears that the electronic effect of substitution outweighs the potential steric hindrance to addition at the outer rings
OMIM-1 and OMIM-5 demonstrate simple 1H/13C NMR spectra, whereas those of OMIM-4 and OMIM-6 are complex indicating the presence of regioisomers, as expected due to the less symmetrical nature of the precursors 2 and 6, respectively
Apparent BET surface areas calculated from these isotherms are 480, 626, 702, and 622 m2 g−1 for OMIM-1, OMIM-4, OMIM5, and OMIM-6, repectively
Summary
Citation for published version: Taylor, RGD, Carta, M, Bezzu, CG, Walker, J, Msayib, KJ, Kariuki, BM & McKeown, N 2014, 'Triptycenebased organic molecules of intrinsic microporosity', Organic letters, vol 16, no. Publisher Rights Statement: ACS AuthorChoice/Editors’ Choice via Creative Commons CC-BY Usage Agreement.
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