Synthesis and gas permeation properties of poly(diphenylacetylenes) having bulky alkyl/silyl and hydroxy groups

Hu, Yanming; Sakaguchi, Toshikazu; Shiotsuki, Masashi; Sanda, Fumio; Masuda, Toshio

doi:10.1016/j.memsci.2006.06.001

Cited by 12 publications

(7 citation statements)

References 24 publications

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“…Fortunately, we were able to do pioneering works and obtain many interesting results in this new area. We are now engaged in challenging subjects that include novel catalysts (e.g., Ru carbenes, 113 highly active Rh-based living polymerization catalyst), construction of new polymer architectures derived from substituted acetylenes (e.g., polymer brushes, 114 dendronbearing polyacetylenes), preparation of highly efficient CO 2 separation membranes based on substituted polyacetylenes, 115 and development of novel functional polymer materials (e.g., organic battery materials). 116 Only about 80 years have passed since the mankind began to synthesize artificial polymers, whereas organisms have spent about four trillion years to develop elaborately designed, highly functional biomacromolecules such as DNA, proteins, and polysaccharides.…”

Section: Discussionmentioning

confidence: 99%

Substituted polyacetylenes

Masuda

2006

J. Polym. Sci. A Polym. Chem.

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392

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This article reviews the chemistry of substituted polyacetylenes developed by our research group, more specifically, development of polymerization catalyst, synthesis of new polymers, elucidation of their structure, investigation of their properties, and development of their functions. The main features are as follows: a number of catalysts based on group 5, 6, and 9 transition metals (Nb, Ta, Mo, W, and Rh) have been developed, which include living polymerization catalysts. By using these catalysts, many new substituted polyacetylenes have been synthesized, whose molecular weights are very high (Mw = 104−106). Most of the polymers are soluble in many common solvents and stable enough in the air unlike polyacetylene. Some of these polymers exhibit interesting functions including high gas permeability and photoelectronic properties. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 165–180, 2007

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Section: Discussionmentioning

confidence: 99%

Substituted polyacetylenes

Masuda

2006

J. Polym. Sci. A Polym. Chem.

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392

222

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“…Hexakis(phenylethynyl)benzene, 21 hexakis(4cyanophenyl)benzene, 19 1,3,5-triethynylbenzene, 22 and 4-(tert-butyldimethylsilyloxy)iodobenzene 23 were prepared according to the established procedure. 1,3,5-Tris(4cyanophenylethynyl)benzene…”

Section: Methodsmentioning

confidence: 99%

“…The other solvents and reagents commercially available were used without further purification. Hexakis(phenylethynyl)benzene, 21 hexakis (4-cyanophenyl)benzene, 19 1,3,5-triethynylbenzene, 22 and 4-(tertbutyldimethylsilyloxy)iodobenzene 23 were prepared according to the established procedure. 1,3,5-Tris(4-cyanophenylethynyl) benzene (1), 24 1,3,5-tris(4-pyridylethynyl)benzene (2), 25 1,3,5tris[4-(ethoxycarbonyl)phenylethynyl]benzene (6), 1,3,5-tris(4carboxyphenylethynyl)benzene (H 3 7) 26 are known literature compounds.…”

Section: Methodsmentioning

confidence: 99%

1,3,5-Tris(functionalised-phenylethynyl)benzene–metal complexes: synthetic survey of mesoporous coordination polymers and investigation of their carbonisation

Kobayashi

Kijima

2008

J. Mater. Chem.

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A series of multicoordinate 1,3,5-tris(functionalised-phenylethynyl)benzenes (1-9) was synthesised, and coordination polymers were constructed from these organic linkers and copper ions in high yields. The carbonisation of the linkers 1-9 afforded a microporous carbon that shows type I adsorption-desorption isotherm. Although most of the coordination polymers prepared in this study turned out to be low porous materials, the coordination polymer 7e prepared from the reaction of 1,3,5-tris(4-carboxyphenylethynyl)benzene tripotassium salt (K 3 7) and copper (II) nitrate was a microporous material in addition to the mesoporous materials (7c and 7d) prepared from the reaction of K 3 7 with copper (II) acetate and copper (II) chloride, respectively. The carbonisation of the coordination polymers unexceptionally brought about an increase of micropore volume. A stepwise analysis of 7c pyrolysed at 350 °C, 600 °C, and 900 °C revealed that the mesoporosity hardly changed upon heat-treatment, which demonstrates, in other words, that microporosity could be successfully added to the mesoporous coordination polymer through the carbonisation process.

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“…Previous presentations of CO 2 /N 2 upper bounds were made by Shida [6,7],H u [8], Khan [9] and Dai [25]. At the time there was no upper bound for this gas pair defined by Robeson.…”

Section: Co 2 /Nmentioning

confidence: 99%

“…A major advantage of Freeman's formulation was that it allowed one to define upper bounds for any gas pairs, or to corroborate an existing gas pair, for example, the two important gas pairs, CO 2 /N 2 [6][7][8][9][10] for greenhouse gas mitigation or N 2 /CH 4 [10], for which Robeson [4] has recently assigned upper bounds. Furthermore, having a mechanistic model gives one insight for improving polymer selectivity/permeability.…”

Section: Introductionmentioning

confidence: 99%

Revisiting the experimental and theoretical upper bounds of light pure gas selectivity–permeability for polymeric membranes

Dal‐Cin

Kumar

Layton

2008

Journal of Membrane Science

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Robeson [L.M. Robeson, J. Membr. Sci. 62 (1991) described "upper bounds" correlating the pure gas selectivity with the permeability of the faster gas, P A . The exponential dependence of the selectivity-permeability trade off, −1/n, according to the relationship˛A /B = P A /P B = k . The theoretical model opened the possibility of setting upper bounds for gas pairs for which experimental upper bounds were not reported. Despite quantitative predictions of both −1/n and k −1/n (oř A/B ) calculated values of˛A /B compared poorly with Robeson's upper bounds for many of the gas pairs. This work revisits Robeson's findings as well as those of Freeman and seeks to improve the predictive accuracy of Freeman's model. Robeson had noted that the low precision of many of the kinetic gas diameters could have contributed to the scatter in his correlation of −1/n and A/B . Considering this hypothesis, the gas diameters were re-estimated using the Error in the Variable Method (EVM) with the regression criterion based on the predicted selectivity at three permeabilites compared to Robeson's upper bounds. Very small changes to the gas diameters, typically <0.09 Å, made a significant improvement in the overall accuracy of the predicted selectivity and the correlation of A/B = −1/n. Freeman's f value, a constant in the E D correlation as a function of the gas collision diameter, was revised from 12,600 to 16,909 cal mol −1 (52.7 to 70.7 KJ mol − 1). Recent predictions of the theoretical upper bound are reviewed and corrections proposed based on Freeman's model and parameters for the gas pairs: N 2 /CH 4 and CO 2 /N 2 .Crown

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Synthesis and gas permeation properties of poly(diphenylacetylenes) having bulky alkyl/silyl and hydroxy groups

Cited by 12 publications

References 24 publications

Substituted polyacetylenes

Substituted polyacetylenes

1,3,5-Tris(functionalised-phenylethynyl)benzene–metal complexes: synthetic survey of mesoporous coordination polymers and investigation of their carbonisation

Revisiting the experimental and theoretical upper bounds of light pure gas selectivity–permeability for polymeric membranes

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