Topic
Norbornene
About: Norbornene is a research topic. Over the lifetime, 5628 publications have been published within this topic receiving 104495 citations. The topic is also known as: norbornylene & norcamphene.
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TL;DR: A class of readily available bifunctional silyl ether-based cyclic olefins that copolymerize efficiently with norbornene-based (macro)monomers to provide copolymers with backbone degradability under mildly acidic aqueous conditions and degradation rates that can be tuned over several orders of magnitude, depending on the sily l ether substituents.
Abstract: Ring-opening metathesis polymerization of norbornene-based (macro)monomers is a powerful approach for the synthesis of macromolecules with diverse compositions and complex architectures. Nevertheless, a fundamental limitation of polymers prepared by this strategy is their lack of facile degradability, limiting their utility in a range of applications. Here we describe a class of readily available bifunctional silyl ether-based cyclic olefins that copolymerize efficiently with norbornene-based (macro)monomers to provide copolymers with backbone degradability under mildly acidic aqueous conditions and degradation rates that can be tuned over several orders of magnitude, depending on the silyl ether substituents. These monomers can be used to manipulate the in vivo biodistribution and clearance rate of polyethylene glycol-based bottlebrush polymers, as well as to synthesize linear, bottlebrush and brush-arm star copolymers with degradable segments. We expect that this work will enable preparation of degradable polymers by ROMP for biomedical applications, responsive self-assembly and improved sustainability.
93 citations
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TL;DR: A total synthesis of cylindramide A has been completed in 19 steps with a tandem ring-opening-ring-closing-cross metathesis that converts a readily available norbornene into an advanced intermediate.
Abstract: A total synthesis of cylindramide A has been completed in 19 steps. The key step of the synthesis is a tandem ring-opening−ring-closing−cross metathesis that converts a readily available norbornene into an advanced intermediate.
92 citations
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TL;DR: In this paper, the capacity of poly(5a)-based cell reached the theoretical value (109 Ah · kg -1 ) of the polymer, while poly(1, 3, and 4) gave polymers insoluble in common organic solvents in 88-100% yields.
Abstract: 2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO)-containing N-propargylamide HC≡CCH 2 NHCO+TEMFO (1), propargyl ester HC≡CCH 2 OCO-4-TEMPO (2), phenylacetylene derivative HC≡CC 6 H 3 -3,4-(CO 2 -4-TEMPO) 2 (3), and norbornene diester monomers, NB-2,3-exo, exo-(CH 2 OCO-4-TEMPO)2 (4), NB-2,3-endo,exo-(COO-4-TEMPO) 2 (5a), NB-2,3-endo,endo-(COO-4-TEMPO)2 (5b) (NB = norbornorbornene, TEMPO = 2,2,6,6-tetramethyl-l-piperidinyloxyl) were synthesized and polymerized with rhodium and ruthenium catalysts. Monomers 2, 5a, and 5b gave polymers with number-average molecular weights of 47000-185000 in 59-100% yields, while 1, 3, and 4 gave polymers insoluble in common organic solvents in 88-100% yields. The capacities of cells fabricated with poly(1), poly(2), and poly(3) were 67, 82, and 23 Ah · kg -1 based on the weight, respectively. The capacity of poly(5a)-based cell reached the theoretical value (109 Ah · kg -1 ) of the polymer.
92 citations
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20 Mar 2019TL;DR: Cross-linked anion exchange membranes (AEMs) synthesized by vinyl addition polymerization of norbornene were prepared for use in anion-exchange membrane electrochemical devices, including fuel.
Abstract: Cross-linked (XL) anion-exchange membranes (AEMs) synthesized by vinyl addition polymerization of norbornene were prepared for use in anion-exchange membrane electrochemical devices, including fuel...
92 citations
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TL;DR: In this article, the effects of both solvent and cocatalyst on catalytic activity in the ethylene polymerization by the (arylmido)(aryloxo)vanadium(V) complex, VCl2(N-2,6-Me 2 C 6 H 3 )(O-2 6 Me 2C 6 H3 ) (1), have been explored in detail.
Abstract: The effects of both Al cocatalyst and solvent on catalytic activity in the ethylene polymerization by the (arylmido)(aryloxo)vanadium(V) complex, VCl2(N-2,6-Me 2 C 6 H 3 )(O-2,6-Me 2 C 6 H 3 ) (1), have been explored in detail. The activity of 5.84 × 10 5 kgPE/molV-h (TOF 2.08 × 10 7 h -1 ) has been achieved by 1/EtAlCl 2 catalyst in CH 2 Cl 2 at 0°C, and the activity in toluene increased in the order: i-Bu 2 AlCl > EtAlCl 2 > Me 2 AlCl > Et 2 AlCl > Et 2 Al(OEt), AlEt 3 , AlMe 3 (negligible activities). Both aluminum alkyl cocatalyst and solvent also affected the catalytic activity and the norbornene (NBE) incorporation in the ethylene/NBE copolymerization using complex 1, whereas the NBE contents were not strongly affected by the kind of aryl oxide ligand in VCl2(N-2,6-Me 2 C 6 H 3 )(OAr) [OAr=O-2,6-Me 2 C 6 H 3 (1), O-2,6-i-Pr 2 C 6 H 3 (2), O-2,6-Ph 2 C 6 H 3 (3)].
92 citations