Block copolymers containing monodisperse segments produced by ring-opening metathesis of cyclic olefins

Cannizzo, Louis F.; Grubbs, Robert H.

doi:10.1021/ma00185a012

Cited by 82 publications

(28 citation statements)

References 4 publications

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“…With ruthenium carbene initiators, polymer length can be regulated by varying the monomer to initiator (M:I) ratio 20. Similarly, defined block copolymers can be synthesized by conducting living ROMP, such that when one monomer is consumed, a second is added 21. Finally, ROMP also provides the means to cap polymer products with unique end groups 22–36…”

Section: Introductionmentioning

confidence: 99%

General Synthetic Route to Cell-Permeable Block Copolymers via ROMP

et al. 2009

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The applications of block copolymers are myriad, ranging from electronics to functionalized resins to therapeutics. The ring-opening metathesis polymerization (ROMP) is an especially valuable reaction for block copolymer assembly because each block can be generated with length control. We sought to use this polymerization to expand the repertoire of block copolymers by implementing a strategy that involves post-polymerization modification of a backbone bearing selectively reactive groups. To this end, we demonstrate that ROMP can be used to synthesize a block copolymer scaffold that possesses three types of functional groups – a succinimidyl ester, an α-chloroacetamide group, and a ketone – each of which can be modified independently. Thus, a single scaffold can be elaborated to afford a wide range of block copolymers. Exploiting this synthetic approach and the length control offered by ROMP, we assemble block copolymers capable of traversing the membrane and entering mammalian cells.

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Section: Introductionmentioning

confidence: 99%

General Synthetic Route to Cell-Permeable Block Copolymers via ROMP

et al. 2009

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“…Finally, ROMP can be used to prepare block copolymers having specific segments and/or end group compositions. 49,50 Based on a previous report of the ROMP of 1,4-(1,1 0 -ferrocenediyl)-1,3-butadiene 3, 32 we chose the highly reactive tungsten-based metathesis initiator, W(vCHC 6 H 4 -o-OMe)(vNPh)[OCMe(CF 3 ) 2 ] 2 (THF), 51 (see Scheme 1) as the ROMP initiator in the studies reported here.…”

Section: Introductionmentioning

confidence: 99%

ROMP of t-butyl-substituted ferrocenophanes affords soluble conjugated polymers that contain ferrocene moieties in the backbone

et al. 2004

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“…Molecular oxygen was thought to facilitate oxidation of the benzylic/allylic position, which then led to intermolecular cross-linking, chain scission, and the ultimate formation of ill-defined materials. Similar studies on related systems by the groups of Grubbs 11 and Schrock 12, 13 further suggested that polymers containing a C–H bond at the readily oxidized benzylic/allylic position undergo rapid decomposition, rendering the polymers unstable and of limited utility.…”

Section: Introductionmentioning

confidence: 75%

Expanding the ROMP Toolbox: Synthesis of Air-Stable Benzonorbornadiene Polymers by Aryne Chemistry

Medina

Maynard

et al. 2017

Macromolecules

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Benzonorbornadiene polymers synthesized by ring-opening metathesis polymerization (ROMP) are typically prone to oxidation at the benzylic/allylic position under ambient conditions. Accordingly, the use of benzonorbornadiene polymers in practical applications has remained limited. In this manuscript, we report the synthesis of poly(benzonorbornadiene) polymers using a strategic blend of benzyne chemistry and ROMP. Through a comparative study, we show that substitution at the benzylic/allylic position prevents oxidative deformation, yet does not inhibit polymerization by common ruthenium catalysts with good control over molecular weight dispersity. We expect the benzyne/ROMP reaction sequence will allow easy access to air-stable benzonorbornadiene polymers for various applications.

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Block copolymers containing monodisperse segments produced by ring-opening metathesis of cyclic olefins

Cited by 82 publications

References 4 publications

General Synthetic Route to Cell-Permeable Block Copolymers via ROMP

General Synthetic Route to Cell-Permeable Block Copolymers via ROMP

ROMP of t-butyl-substituted ferrocenophanes affords soluble conjugated polymers that contain ferrocene moieties in the backbone

Expanding the ROMP Toolbox: Synthesis of Air-Stable Benzonorbornadiene Polymers by Aryne Chemistry

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