Regioselective cross metathesis for block and heterotelechelic polymer synthesis

Radlauer, Madalyn R.; Matta, Megan E.

doi:10.1039/c6py01231k

Cited by 39 publications

(32 citation statements)

References 40 publications

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“…This resulted in the synthesis of polymers with two different chain ends in a thermodynamically driven catalytic process. While mechanistically a heterotelechelic polymer was produced, one of the polymer end‐groups was an alkyl chain that did not allow for post‐polymerization functionalization . Katayama et al.…”

Section: Figurementioning

confidence: 99%

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Heterotelechelic Polymers by Ring‐Opening Metathesis and Regioselective Chain Transfer

et al. 2017

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Heterotelechelic polymers were synthesized by a kinetic telechelic ring-opening metathesis polymerization method relying on the regioselective cross-metathesis of the propagating Grubbs' first-generation catalyst with cinnamyl alcohol derivatives. This procedure allowed the synthesis of hetero-bis-end-functional polymers in a one-pot setup. The molecular weight of the polymers could be controlled by varying the ratio between cinnamyl alcohol derivatives and monomer. The end functional groups can be changed using different aromatically substituted cinnamyl alcohol derivatives. Different monomers were investigated and the presence of the functional groups was shown by NMR spectroscopy and MALDI-ToF mass spectrometry. Labeling experiments with dyes were conducted to demonstrate the orthogonal addressability of both chain ends of the heterotelechelic polymers obtained.

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Section: Figurementioning

confidence: 99%

“…Heterotelechelic poly(norbornene)s were obtained in a kinetically controlled catalytic process . Both former cases rely either on specially synthesized monomers or chain transfer agents, both typically prepared over several synthetic steps and are compatible with norbornene derivatives.…”

Section: Figurementioning

confidence: 99%

Heterotelechelic Polymers by Ring‐Opening Metathesis and Regioselective Chain Transfer

et al. 2017

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“…[30][31][32][33][34][35] Fewer examples have been reported on the synthesis of heterotelechelic polymers using only catalytic quantities of transition metal complex. [36][37][38][39] However,n one of the examples given above can be considered as living, as molecular weight distributions are typically broad, and block copolymers cannot be made.…”

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Catalytic Living Ring Opening Metathesis Polymerisation: The Importance of Ring Strain in Chain Transfer Agents

2019

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Ar ecently developed catalytic living ring opening metathesis polymerisation (ROMP) was investigated using as eries of reversible chain transfer agents (CTA) carrying either cyclopentene or cyclohexene rings,differing only in ring strain. All cyclopentene derivatives examined showed significantly faster reaction rates than the corresponding cyclohexene derivatives.This resulted in lower molecular weight dispersities and better control of the molecular weight for the cyclopentene compared to the cyclohexene CTAs.Both Grubbs second and thirdgeneration catalysts could be employed in catalytic living ROMP using cyclopentene CTAd erivatives.T he kinetics of different CTAs were studied, blockc opolymers were synthesised and residual ruthenium quantified by ICP-OES.A ll polymers were fully characterised by NMR, GPC and MALDI-ToF mass spectrometry.T he new cyclopentene CTAs are readily synthesised in af ew straightforwards teps and provide faster reaction kinetics than all previously reported reversible CTAs.

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“…[27] In one case, a regio-selective chain transfer agent was exploited to prepare hetero-telechelic polymers. [28] Functional polymer initiation followed by functional termination will allow the synthesis of hetero-telechelic polymers. Functional initiators can be prepared by cross-metathesis reactions using functional acyclic olefins.…”

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Functional Metathesis Catalyst Through Ring Closing Enyne Metathesis: One Pot Protocol for Living Heterotelechelic Polymers

et al. 2018

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Enyne ring closing metathesis has been used to synthesize functional group carrying metathesis catalysts from a commercial (Ru-benzylidene) Grubbs' catalysts. The new Grubbs-type ruthenium carbene was used to synthesize living heterotelechelic ROMP polymers without any intermediate purification. Olefin metathesis with a mono substituted alkyne followed by ring closing metathesis with an allylic ether provided efficient access to new functional group carrying metathesis catalysts. Different functional benzylidene and alkylidene derivatives have been investigated in the synthesis of heterotelechelic polymers in one pot.

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Regioselective cross metathesis for block and heterotelechelic polymer synthesis

Abstract: Cross metathesis of polymers made from 3-substituted cyclooctene derivatives produce regio- and stereoregular block and hetereotelechelic polymers.

Cited by 39 publications

References 40 publications

Heterotelechelic Polymers by Ring‐Opening Metathesis and Regioselective Chain Transfer

Heterotelechelic Polymers by Ring‐Opening Metathesis and Regioselective Chain Transfer

Catalytic Living Ring Opening Metathesis Polymerisation: The Importance of Ring Strain in Chain Transfer Agents

Functional Metathesis Catalyst Through Ring Closing Enyne Metathesis: One Pot Protocol for Living Heterotelechelic Polymers

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