MEH-PPV by microwave assisted ring-opening metathesis polymerisation

Spring, Andrew M.; Yu, Chin‐Yang; Horie, Masaki; Turner, Michael L.

doi:10.1039/b901075k

Cited by 54 publications

(44 citation statements)

References 25 publications

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“…This 5:5 ratio implies the same environment for each double bond (cis and trans) with a location of one methoxy and one 2-ethylhexyloxy substituent in proximity to each double bond. 34 Therefore, a coordination of the methoxy substituent to ruthenium during the polymerization process can be concluded.…”

Section: Resultsmentioning

confidence: 99%

Reactivity Studies of Alkoxy-Substituted [2.2]Paracyclophane-1,9-dienes and Specific Coordination of the Monomer Repeating Unit during ROMP

Menk¹,

Mondeshki²,

Dudenko

et al. 2015

Macromolecules

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The polymerization of alkoxy-substituted [2.2]-paracyclophane-1,9-dienes via ring-opening metathesis polymerization (ROMP) to obtain soluble poly(pphenylenevinylene)s is a versatile method due to its living nature which enables the possibility of block copolymerization and end group modification. However, detailed studies on the reactivity behavior and the polymerization process of alkoxysubstituted [2.2]paracyclophane-1,9-dienes have not been reported so far. Herein we present a detailed study on the varying tendencies of the four isomers of dimethoxy-(2-ethylhexyloxy)-[2.2]paracyclophane-1,9-diene to undergo ROMP. Therefore, we carried out polymerization combining all individual isomers with five different metathesis catalysts and collected initiation and propagation kinetics for various combinations. Furthermore, we revealed a specific coordination of the monomer repeating unit to the catalyst during the polymerization process and succeeded to polymerize not only the pseudogeminal isomers but also one of the pseudo-ortho isomers.

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Section: Resultsmentioning

confidence: 99%

Reactivity Studies of Alkoxy-Substituted [2.2]Paracyclophane-1,9-dienes and Specific Coordination of the Monomer Repeating Unit during ROMP

Menk¹,

Mondeshki²,

Dudenko

et al. 2015

Macromolecules

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“…A direct route to soluble PPVs via ROMP of alkoxy or alkyl substituted paracyclophanedienes in the presence of the second generation Grubbs’ initiator has been reported by Yu and Turner . They demonstrated that the resulting PPVs exhibited predictable and well‐controlled molecular weights with low PDI by varying the monomer to initiator ratio, thereby confirming the living nature of the polymerization.…”

Section: Introductionmentioning

confidence: 78%

Soluble Phenylenevinylene Polymers Containing Tetraphenylethene Units by Ring‐Opening Metathesis Polymerization

Lai

2018

Macro Chemistry & Physics

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Soluble phenylenevinylene polymers containing tetraphenylethene units are synthesized by ring‐opening metathesis polymerization of 4‐triphenylvinylphenyl‐[2.2]paracyclophane‐1,9‐diene in the presence of the second generation Grubbs’ initiator. Various polymer molecular weights can be obtained by altering the monomer to initiator ratio. Isomerization is successfully conducted in dilute polymer solution under a UV light irradiation. The as‐prepared polymers with longer chain lengths show relatively strong emission with a photoluminescence quantum yield of up to 43% in solution. Aggregation induced emission is observed for the polymers containing the cis–trans microstructures when the water fraction reached 80% in water/THF mixture. The morphologies of the polymers containing the cis–trans and trans microstructures are distinctive which reveal sphere‐like particles and network‐like structures, respectively. These polymers are promising candidates for potential uses in fluorescence applications.

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“…[30] MEH-PPV displays am ax absorption peak at l max = 510 nm, as well as an emission around 550 nm, with aprominent shoulder at 600 nm. [30] MEH-PPV displays am ax absorption peak at l max = 510 nm, as well as an emission around 550 nm, with aprominent shoulder at 600 nm.…”

Section: Angewandte Chemiementioning

confidence: 99%

Poly(arylenevinylene)s through Ring‐Opening Metathesis Polymerization of an Unsymmetrical Donor‐Acceptor Cyclophane

Elacqua

Gregor

2019

Angew Chem Int Ed

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Reported are well-defined donor-acceptor alternating copolymers prepared using ring-opening metathesis polymerization (ROMP). Unsymmetrical cyclophanedienes comprising electron-donating (4-methoxy-1-(2-ethylhexyl)oxy)benzene( MEH) and electron-accepting benzothiadiazole (BT) rings were synthesized from the corresponding [3.3]dithiaparacyclophanes.R OMP of the strained unsymmetrical and "electronically-ambiguous" cyclophanedienes proceeded in ac ontrolled manner in the presence of either Hoveyda-GrubbsI Io rG rubbs II initiator in wake of both steric and electronic encumbrance.T he resulting polymers, comprising alternating BT and MEH-PPV units,are achieved in molecular weights exceeding 20k with values ranging from 1.1-1.4. The living nature of the polymerization is verified through the formation of rod-coil and rod-rod block copolymers.O ur strategy to develop previously unrealized polymers from functional building blocks featuring alocked-in D-A unit is significant in afield striving to achieve well-defined and sequence-specific materials.

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MEH-PPV by microwave assisted ring-opening metathesis polymerisation

Abstract: Excellent control in the synthesis of MEH-PPV can be achieved by microwave assisted, ring-opening metathesis polymerisation (ROMP) of [2.2]paracyclophanedienes.

Cited by 54 publications

References 25 publications

Reactivity Studies of Alkoxy-Substituted [2.2]Paracyclophane-1,9-dienes and Specific Coordination of the Monomer Repeating Unit during ROMP

Reactivity Studies of Alkoxy-Substituted [2.2]Paracyclophane-1,9-dienes and Specific Coordination of the Monomer Repeating Unit during ROMP

Soluble Phenylenevinylene Polymers Containing Tetraphenylethene Units by Ring‐Opening Metathesis Polymerization

Poly(arylenevinylene)s through Ring‐Opening Metathesis Polymerization of an Unsymmetrical Donor‐Acceptor Cyclophane

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