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The synthesis of organic molecules of intrinsic microporosity designed to frustrate efficient molecular packing

Taylor, Rupert G. D., Bezzu, C. Grazia, Carta, Mariolino, Msayib, Kadhum J., Walker, Jonathan, Short, Rhys, Kariuki, Benson and McKeown, Neil B. 2016. The synthesis of organic molecules of intrinsic microporosity designed to frustrate efficient molecular packing. Chemistry - A European Journal 22 (7) , pp. 2466-2472. 10.1002/chem.201504212

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Efficient reactions between fluorine-functionalised biphenyl and terphenyl derivatives with catechol-functionalised terminal groups provide a route to large, discrete organic molecules of intrinsic microporosity (OMIMs) that provide porous solids solely by their inefficient packing. By altering the size and substituent bulk of the terminal groups, a number of soluble compounds with apparent BET surface areas in excess of 600 m2 g−1 are produced. The efficiency of OMIM structural units for generating microporosity is in the order: propellane>triptycene>hexaphenylbenzene>spirobifluorene>naphthyl=phenyl. The introduction of bulky hydrocarbon substituents significantly enhances microporosity by further reducing packing efficiency. These results are consistent with findings from previously reported packing simulation studies. The introduction of methyl groups at the bridgehead position of triptycene units reduces intrinsic microporosity. This is presumably due to their internal position within the OMIM structure so that they occupy space, but unlike peripheral substituents they do not contribute to the generation of free volume by inefficient packing.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley-Blackwell
ISSN: 0947-6539
Date of First Compliant Deposit: 30 March 2016
Last Modified: 05 Jul 2019 10:38

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