Microporous hyper-cross-linked polyacetylene networks: Covalent structure and texture modification by reversible Schiff-base chemistry

Bashta, Bogdana; Hašková, Alena; Faukner, Tomáš; Elsawy, Moataz A.; Šorm, David; Brus, Jiřı́; Sedláček, Jan

doi:10.1016/j.eurpolymj.2020.109914

Cited by 5 publications

(3 citation statements)

References 65 publications

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“…We recently reported hyper-cross-linked polyacetylene networks with aromatic template segments covalently attached to the scaffold via azomethine links. The postpolymerization hydrolysis of these links and the removal of template molecules led to a significant modification of the micropore size distribution and the specific surface area of the POPs [ 47 , 48 ]. In some cases, even non-porous networks were modified into POPs with a specific surface area of about 500 m 2 /g by this templating approach [ 48 ].…”

Section: Introductionmentioning

confidence: 99%

Combining Polymerization and Templating toward Hyper-Cross-Linked Poly(propargyl aldehyde)s and Poly(propargyl alcohol)s for Reversible H2O and CO2 Capture and Construction of Porous Chiral Networks

et al. 2023

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Two series of hyper-cross-linked microporous polyacetylene networks containing either -[CH=C(CH=O)]- or -[CH=C(CH2OH)]- monomeric units are reported. Networks are prepared by chain-growth copolymerization of acetal-protected propargyl aldehyde and acetal-protected propargyl alcohol with a 1,3,5-triethynylbenzene cross-linker followed by hydrolytic deprotection/detemplating. Deprotection not only liberates reactive CH=O and CH2OH groups in the networks but also modifies the texture of the networks towards higher microporosity and higher specific surface area. The final networks with CH=O and CH2OH groups attached directly to the polyene main chains of the networks have a specific surface area from 400 to 800 m2/g and contain functional groups in a high amount, up to 9.6 mmol/g. The CH=O and CH2OH groups in the networks serve as active centres for the reversible capture of CO2 and water vapour. The water vapour capture capacities of the networks (up to 445 mg/g at 297 K) are among the highest values reported for porous polymers, making these materials promising for cyclic water harvesting from the air. Covalent modification of the networks with (R)-(+)-3-aminopyrrolidine and (S)-(+)-2-methylbutyric acid enables the preparation of porous chiral networks and shows networks with CH=O and CH2OH groups as reactive supports suitable for the anchoring of various functional molecules.

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Section: Introductionmentioning

confidence: 99%

Combining Polymerization and Templating toward Hyper-Cross-Linked Poly(propargyl aldehyde)s and Poly(propargyl alcohol)s for Reversible H2O and CO2 Capture and Construction of Porous Chiral Networks

et al. 2023

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“…In this case, the nitrogen‐containing groups simultaneously contributed to the formation of the porous texture. POPs of this type included networks with tertiary amine‐type knots [ 19 ] and networks with amine‐, [ 20 ] aminal‐, [ 21 ] azomethine‐, [ 22 ] and azo‐type [ 23 ] links. The introduction of basic nitrogen centers into networks in the form of heterocyclic building blocks represents another path to the POPs discussed.…”

Section: Introductionmentioning

confidence: 99%

“…[ 46 ] The resulting POPs consisted of polyacetylene (polyene) main chains that were hyper‐cross‐linked by arene‐type cross‐links. [ 22 ] Polyacetylene POPs were active as heterogeneous catalysts, [ 47 ] sorbents, [ 10 ] and porous fluorescent materials. [ 48 ]…”

Section: Introductionmentioning

confidence: 99%

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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Microporous hyper-cross-linked polyacetylene networks: Covalent structure and texture modification by reversible Schiff-base chemistry

Cited by 5 publications

References 65 publications

Combining Polymerization and Templating toward Hyper-Cross-Linked Poly(propargyl aldehyde)s and Poly(propargyl alcohol)s for Reversible H2O and CO2 Capture and Construction of Porous Chiral Networks

Combining Polymerization and Templating toward Hyper-Cross-Linked Poly(propargyl aldehyde)s and Poly(propargyl alcohol)s for Reversible H2O and CO2 Capture and Construction of Porous Chiral Networks

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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