期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 7, 页码 2466-2472出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504212
关键词
adsorption; aromatic nucleophilic substitution; microporous materials; molecular packing; triptycene
资金
- EPSRC, UK [EP/H024034, EP/K008102/2]
- EPSRC [EP/K008102/1, EP/H024034/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K008102/1, EP/H024034/1] Funding Source: researchfish
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.
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