The Synthesis of Organic Molecules of Intrinsic Microporosity Designed to Frustrate Efficient Molecular Packing
| Autor: | Rhys Short, Jonathan Walker, Benson M. Kariuki, Mariolino Carta, Neil B. McKeown, C. Grazia Bezzu, Rupert G. D. Taylor, Kadhum J. Msayib |
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| Rok vydání: | 2016 |
| Předmět: |
Substituent
CAGE COMPOUNDS 02 engineering and technology 010402 general chemistry Atomic packing factor 01 natural sciences Catalysis chemistry.chemical_compound molecular packing Terphenyl triptycene Organic chemistry QD Hexaphenylbenzene PIMS Biphenyl chemistry.chemical_classification CRYSTAL Full Paper Chemistry microporous materials Organic Chemistry aromatic nucleophilic substitution HYDROGEN STORAGE General Chemistry Microporous Materials | Hot Paper FRAMEWORKS Full Papers 021001 nanoscience & nanotechnology GAS-ADSORPTION FREE-VOLUME 0104 chemical sciences Propellane Crystallography Hydrocarbon adsorption Triptycene HIGH SURFACE-AREAS SEPARATION POLYMERS 0210 nano-technology |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) Taylor, R G D, Bezzu, C G, Carta, M, Msayib, K J, Walker, J, Short, R, Kariuki, B M & McKeown, N B 2016, ' The Synthesis of Organic Molecules of Intrinsic Microporosity Designed to Frustrate Efficient Molecular Packing ', Chemistry-A European Journal, vol. 22, no. 7, pp. 2466-2472 . https://doi.org/10.1002/chem.201504212 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201504212 |
| Popis: | 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 600m(2)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. |
| Databáze: | OpenAIRE |
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