Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials

Three new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)2 as an initiator. The resulting polymers had very high average molecular weights (Mw) of 1.4–4.8 × 106...

Full description

Bibliographic Details
Main Authors:	Yu Zang, Yinghui Lun, Masahiro Teraguchi, Takashi Kaneko, Hongge Jia, Fengjuan Miao, Xunhai Zhang, Toshiki Aoki
Format:	Article
Language:	English
Published:	MDPI AG 2020-08-01
Series:	Membranes
Subjects:	polyphenylacetylene cis-cisoid conformation cis-transoid conformation carbamate group membrane-forming ability solubility
Online Access:	https://www.mdpi.com/2077-0375/10/9/199

id	doaj-774358e484ab48669592b5b1ccbbbf50
record_format	Article
spelling	doaj-774358e484ab48669592b5b1ccbbbf502020-11-25T03:11:30ZengMDPI AGMembranes2077-03752020-08-011019919910.3390/membranes10090199Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane MaterialsYu Zang0Yinghui Lun1Masahiro Teraguchi2Takashi Kaneko3Hongge Jia4Fengjuan Miao5Xunhai Zhang6Toshiki Aoki7Key laboratory of polymer matrix composites, Heilongjiang Province, College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, Heilongjiang 161006, ChinaDepartment of Materials and Chemical Engineering, Hunan Institute of Technology, Hengyang, Hunan 421002, ChinaChemistry and Chemical Engineering, Graduate School of Science and Technology, Niigata University, Ikarashi 2-8050, Nishi-ku, Niigata 950-2181, JapanChemistry and Chemical Engineering, Graduate School of Science and Technology, Niigata University, Ikarashi 2-8050, Nishi-ku, Niigata 950-2181, JapanKey laboratory of polymer matrix composites, Heilongjiang Province, College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, Heilongjiang 161006, ChinaCollege of Communications and Electronics Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, Heilongjiang 161006, ChinaKey laboratory of polymer matrix composites, Heilongjiang Province, College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, Heilongjiang 161006, ChinaKey laboratory of polymer matrix composites, Heilongjiang Province, College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, Heilongjiang 161006, ChinaThree new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)<sub>2</sub> as an initiator. The resulting polymers had very high average molecular weights (<i>Mw</i>) of 1.4–4.8 × 10<sup>6</sup>, with different solubility and membrane-forming abilities. The polymer having two carbamate groups and no hydroxy groups in the monomer unit showed the best solubility and membrane-forming ability among the three polymers. In addition, the oxygen permeability coefficient of the membrane was more than 135 times higher than that of a polymer having no carbamate groups and two hydroxy groups in the monomer unit with maintaining similar oxygen permselectivity. A better performance in membrane-forming ability and oxygen permeability may be caused by a more extended and flexible cis-transoid conformation and lower polarity. On the other hand, the other two new polymers having one carbamate group and two hydroxy groups in the monomer unit showed lower performances in membrane-forming abilities and oxygen permeabilities. It may be caused by a very tight cis-cisoid conformation, which was maintained by intramolecular hydrogen bonds.https://www.mdpi.com/2077-0375/10/9/199polyphenylacetylenecis-cisoid conformationcis-transoid conformationcarbamate groupmembrane-forming abilitysolubility
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Yu Zang Yinghui Lun Masahiro Teraguchi Takashi Kaneko Hongge Jia Fengjuan Miao Xunhai Zhang Toshiki Aoki
spellingShingle	Yu Zang Yinghui Lun Masahiro Teraguchi Takashi Kaneko Hongge Jia Fengjuan Miao Xunhai Zhang Toshiki Aoki Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials Membranes polyphenylacetylene cis-cisoid conformation cis-transoid conformation carbamate group membrane-forming ability solubility
author_facet	Yu Zang Yinghui Lun Masahiro Teraguchi Takashi Kaneko Hongge Jia Fengjuan Miao Xunhai Zhang Toshiki Aoki
author_sort	Yu Zang
title	Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials
title_short	Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials
title_full	Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials
title_fullStr	Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials
title_full_unstemmed	Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials
title_sort	synthesis of cis-cisoid or cis-transoid poly(phenyl-acetylene)s having one or two carbamate groups as oxygen permeation membrane materials
publisher	MDPI AG
series	Membranes
issn	2077-0375
publishDate	2020-08-01
description	Three new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)<sub>2</sub> as an initiator. The resulting polymers had very high average molecular weights (<i>Mw</i>) of 1.4–4.8 × 10<sup>6</sup>, with different solubility and membrane-forming abilities. The polymer having two carbamate groups and no hydroxy groups in the monomer unit showed the best solubility and membrane-forming ability among the three polymers. In addition, the oxygen permeability coefficient of the membrane was more than 135 times higher than that of a polymer having no carbamate groups and two hydroxy groups in the monomer unit with maintaining similar oxygen permselectivity. A better performance in membrane-forming ability and oxygen permeability may be caused by a more extended and flexible cis-transoid conformation and lower polarity. On the other hand, the other two new polymers having one carbamate group and two hydroxy groups in the monomer unit showed lower performances in membrane-forming abilities and oxygen permeabilities. It may be caused by a very tight cis-cisoid conformation, which was maintained by intramolecular hydrogen bonds.
topic	polyphenylacetylene cis-cisoid conformation cis-transoid conformation carbamate group membrane-forming ability solubility
url	https://www.mdpi.com/2077-0375/10/9/199
work_keys_str_mv	AT yuzang synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT yinghuilun synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT masahiroteraguchi synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT takashikaneko synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT honggejia synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT fengjuanmiao synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT xunhaizhang synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials AT toshikiaoki synthesisofciscisoidorcistransoidpolyphenylacetyleneshavingoneortwocarbamategroupsasoxygenpermeationmembranematerials
_version_	1724653747030720512

Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials

Similar Items