Synthesis of hyper-cross-linked microporous poly(phenylacetylene)s having aldehyde and other groups and their chemisorption and physisorption ability

Havelková, Lucie; Hašková, Alena; Bashta, Bogdana; Brus, Jiřı́; Lhotka, Miloslav; Vrbková, Eva; Kindl, Martin; Vyskočilová, Eliška; Sedláček, Jan

doi:10.1016/j.eurpolymj.2019.02.039

Cited by 10 publications

(12 citation statements)

References 46 publications

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“…Recently, we reported the synthesis of micro/mesoporous polyacetylene network decorated with aldehyde groups by means of chain‐growth polymerization of 3,5‐diethynylbenzaldehyde ( S BET =916 m 2 ⋅ g −1 ). The parent network was transformed by condensation reaction with ethylenediamine into NH 2 groups bearing PPC organocatalyst ( S BET =649 m 2 ⋅ g −1 ) active in aldol condensation . Several articles described the preparation of acid PPCs by means of sulfonation of aromatic segments of parent porous networks.…”

Section: Introductionmentioning

confidence: 99%

“…The parent network was transformed by condensation reaction with ethylenediamine into NH 2 groups bearing PPC organocatalyst (S BET = 649 m 2 · g À 1 ) active in aldol condensation. [24] Several articles described the preparation of acid PPCs by means of sulfonation of aromatic segments of parent porous networks. The step-growth knitting polymerization of various arenes (carbazole, [25] phenol, bisphenol A and 2-naphthol [26,27] and truxene [28] ) was used to prepare parent microporous networks, which were subsequently sulfonated by chlorosulfonic acid to PPCs decorated with SO 3 H groups in the amount of from 0.85 to 3.7 mmol · g À 1 .…”

Section: Introductionmentioning

confidence: 99%

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Sulfonated Hyper‐cross‐linked Porous Polyacetylene Networks as Versatile Heterogeneous Acid Catalysts

et al. 2019

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Two highly sulfonated micro/mesoporous polymers, P(1,3‐DEB)‐SO3H and P(1,4‐DEB)‐SO3H, with permanent porosity, the specific surface area about 550 m2 ⋅ g−1 and the content of SO3H groups of 2.7 mmol ⋅ g−1 were prepared as new acid Porous Polymer Catalysts, PPCs. The PPCs were achieved by easy sulfonation of parent hyper‐cross‐linked micro/mesoporous polyacetylene‐type networks resulting from a chain‐growth homopolymerization of 1,3‐ and 1,4‐diethynylbenzenes. New PPCs are reported as highly active and reusable heterogeneous catalysts of esterification of fatty acids with methanol and ethanol, Prins cyclization of aldehydes with isoprenol and intramolecular Prins cyclization of citronellal to isopulegol. The catalytic activity of the micro/mesoporous PPCs (TON values up to 522 mol ⋅ mol−1) was higher than that of commercial polymer‐based heterogeneous catalyst Amberlyst 15 possessing gel texture without permanent pores and that of p‐toluenesulfonic acid applied as a homogeneous catalyst.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sulfonated Hyper‐cross‐linked Porous Polyacetylene Networks as Versatile Heterogeneous Acid Catalysts

et al. 2019

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“…In particular, POPs containing basic nitrogen groups or segments are of great interest from the point of view of application. Nitrogen groups of this type positively affect the adsorption properties of POPs, especially toward the acid adsorptives, [ 6,9,10 ] water, [ 11,12 ] and metal ions. [ 13 ] These groups can also serve as basic organocatalytic centers [ 10,14 ] or proligands in construction of heterogeneous organometallic catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…Nitrogen groups of this type positively affect the adsorption properties of POPs, especially toward the acid adsorptives, [ 6,9,10 ] water, [ 11,12 ] and metal ions. [ 13 ] These groups can also serve as basic organocatalytic centers [ 10,14 ] or proligands in construction of heterogeneous organometallic catalysts. [ 15,16 ] Due to the trivalent nature of nitrogen atoms, it is possible to incorporate basic nitrogen groups into POPs in various ways.…”

Section: Introductionmentioning

confidence: 99%

“…Several POPs with amino and amido groups attached as substituents to the hydrocarbon segments of the networks have been described in the literature. [ 10,17,18 ] The incorporation of nitrogen‐containing groups in the form of network links and knots has been more frequent. In this case, the nitrogen‐containing groups simultaneously contributed to the formation of the porous texture.…”

Section: Introductionmentioning

confidence: 99%

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Microporous Hyper‐Cross‐Linked Polymers with High and Tuneable Content of Pyridine Units: Synthesis and Application for Reversible Sorption of Water and Carbon Dioxide

Hašková

Bashta

Titlová

et al. 2021

Macromol. Rapid Commun.

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New hyper‐cross‐linked porous organic polymers (POPs) with a high content of pyridine segments (7.86 mmol pyridine g−1), and a micro/mesoporous texture are reported. The networks are achieved by the chain‐growth homopolymerization of 2,6‐ and 3,5‐diethynylpyridines. The pyridine segments form links interconnecting the polyacetylene main chains in these networks. The content of pyridine segments in the networks can be tuned by copolymerizing diethynylpyridines with 1,3‐diethynylbenzene. The pyridine rings in the networks serve as base and hydrophilic centers for the sorption of CO2 and water. The homopolymer pyridine networks are highly efficient in the low‐pressure adsorption/desorption of CO2. This sorption mode is promising for the postcombustion removal of CO2 from the fuel gas. The poly(3,5‐diethynylpyridine) network exhibits high efficiency in capturing and releasing water vapor (determined capacity 376 mg g−1 at 298 K and relative humidity (RH) = 90% is one of the highest values reported for POPs) and is a promising material for the cyclic water harvesting from air. The reported networks are characterized by 13C cross‐polarization magic angle spinning NMR, thermogravimetric analysis, and N2 adsorption/desorption and their efficiency in CO2 and H2O capturing is discussed in relation to the content and type of incorporated pyridine segments.

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Rh(I) Catalyzed Polymerization of Propargylated Monosaccharides to Electrospinable Helically Chiral Linear Polyacetylenes and Sorption‐Active Porous Polyacetylene Networks

Vaňková,

Havelková,

Brus

et al. 2024

Journal of Polymer Science

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We report the Rh(I)‐catalyzed chain‐growth polymerizations of propargylated monosaccharides to form π‐conjugated polyacetylene‐type products with the monosaccharide substituents attached to the polyacetylene backbone via short methylene spacers. The homopolymerization provides helically chiral linear polyacetylenes of Mw ~ 20,000 soluble in either water (monosaccharide substituents with free OH groups) or organic solvents (acetylated monosaccharide substituents). The methodology is established for the transformation of prepared chiral polymers into fibers (average diameter ~2.7 μm) taking advantage of the electrospinning technique. Copolymerization of propargylated monosaccharides with 1,3,5‐triethynylbenzene cross‐linker provides hyper‐cross‐linked polyacetylene networks with monosaccharide units content up to 46 wt.%, permanent micro/mesoporosity and SBET area up to 482 m2 g−1. The monosaccharide substituents of the networks serve as centers active in reversible isothermal adsorption of water vapor from the air. The achieved H2O capture capacity of 200 mg g−1 (298 K, RH = 90%) shows monosaccharides as promising (co)building blocks for the construction of porous materials effective in water harvesting from air.

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Synthesis of hyper-cross-linked microporous poly(phenylacetylene)s having aldehyde and other groups and their chemisorption and physisorption ability

Cited by 10 publications

References 46 publications

Sulfonated Hyper‐cross‐linked Porous Polyacetylene Networks as Versatile Heterogeneous Acid Catalysts

Sulfonated Hyper‐cross‐linked Porous Polyacetylene Networks as Versatile Heterogeneous Acid Catalysts

Microporous Hyper‐Cross‐Linked Polymers with High and Tuneable Content of Pyridine Units: Synthesis and Application for Reversible Sorption of Water and Carbon Dioxide

Rh(I) Catalyzed Polymerization of Propargylated Monosaccharides to Electrospinable Helically Chiral Linear Polyacetylenes and Sorption‐Active Porous Polyacetylene Networks

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