Ring-Opening Metathesis Polymerization of Coumarin-Containing Norbornene

Tlenkopatchev, Mikhail A.; Fomine, Serguei; Fomina, Lioudmila; Gaviño, Rubén; Ogawa, Teiichiro

doi:10.1295/polymj.29.622

Cited by 29 publications

(31 citation statements)

References 11 publications

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“…The monomer olefinic signals between 5.65 and 6.1 are replaced by a new signal with a maximum 5.30 ppm corresponding to the linear olefinic protons of the predominant trans double bond of the polymer. 10 The 13 C NMR spectrum (Figure 2) also suggests that the polymer contains predominantly trans double bonds and consists of aromatic peaks at 128-130 ppm., four different olefinic carbons of polymer chain from 131.4 to 135.7 ppm. corresponding to head to tail and tail to head enchaiments along the chain.…”

Section: Resultsmentioning

confidence: 97%

“…corresponding to head to tail and tail to head enchaiments along the chain. 10 Signals at 74-76 ppm. and 20.08 ppm.…”

Section: Resultsmentioning

confidence: 99%

“…9,10 The norbornene monomers are attractive due to facile functionalization, high reactivity in ROMP and in the ring-preserving polymerization. 11,12 The high molecular weight functionalized polynorbornene with good mechanical properties can be obtained by ROMP using appropriate catalysts tolerating functional groups.…”

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confidence: 99%

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Synthesis and Oxygen Permeability of Polynorbornene with Tosylate Side Chain Group

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Tlenkopatchev

Ogawa

et al. 2002

Polym J

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ABSTRACT:A new oxygen/nitrogen separation membrane based on a polynorbornene with tosylate side chain group was synthesized using well-defined vinylidene ruthenium catalysts. The permeability, separation factor, diffusion and solubility coefficients of a polynorbornene membrane were studied. The introduction of tosylate group into the fivemembered ring of the polynorbornene main chain results in increase of T g and significant improvement in selectivity for O 2 /N 2 .KEY WORDS Norbornene with Tosylate Substituent / Metathesis Polymerization / Ruthenium Catalysts / Polynorbornene with Tosylate Side Chain Group / Oxygen Permeability / The separation and recovery of oxygen/nitrogen from air using polymer membranes have gained much attention. 1, 2 For example, oxygen-enriched air can be used for medical applications, for oxidation processes of chemicals, for enhanced fuel combustion, etc. Polynorbornenes have been the subject of investigations for potential uses in packaging and gas separation. 3 Thus, the permeability and sorption properties of ring-opened polynorbornenes with silicon and fluorine-containing side chain groups were reported. [4][5][6] The authors 7, 8 studied the gas transport properties of ring-preserved polynorbornenes prepared via addition polymerization route.There are many investigations on the preparation of functionalized polymers by ring-opening metathesis polymerization (ROMP) of norbornene derivatives. 9,10 The norbornene monomers are attractive due to facile functionalization, high reactivity in ROMP and in the ring-preserving polymerization. 11,12 The high molecular weight functionalized polynorbornene with good mechanical properties can be obtained by ROMP using appropriate catalysts tolerating functional groups.The high tolerance of heteroatoms and protic functionalities makes Ru containing compounds very attractive catalysts for metathesis of the various polar monomers. Early it was demonstrated that simple ruthenium complexes can be activated toward olefin metathesis by addition of diazoesters as carbene source. 13 The authors 14, 15 used diphenyl cyclopropene and diazoalkanes as carbene source for the preparation of novel alkylidene ruthenium complexes that are highly efficient catalysts for olefin metathesis and tolerate a large number of polar functional groups.Recently the efficiency of the new vinylidene ruthenium(II) complexes for ROMP of norbornene derivatives has been reported. 16 The present study describes the synthesis of polynorbornene with tosylate side chain group via ROMP of 2-(tosylamethyl)norborn-5-ene using accessible ruthenium vinylidene catalysts and characterization of this polynorbornene for oxygen/nitrogen permeability. EXPERIMENTAL MaterialsPolymerization solvents were distilled over calcium hydride. RuCl 2 (PR 3 ) 3 and Cl 2 (PR 3 ) 2 Ru=C=CH(t-Bu) (R=PPh 3 , PCy 3 ) were prepared according to the literature. 16,17 Other reagents (Aldrich) were used as recieved. 2-(Tosylamethyl)norborn-5-ene (TNB) was prepared as described previously (Scheme 1). 12 Polymeriz...

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Section: Resultsmentioning

confidence: 97%

“…corresponding to head to tail and tail to head enchaiments along the chain. 10 Signals at 74-76 ppm. and 20.08 ppm.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Oxygen Permeability of Polynorbornene with Tosylate Side Chain Group

Contreras

Tlenkopatchev

Ogawa

et al. 2002

Polym J

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“…All the molecules were synthesized employing a simple procedure avoiding multistep reactions in good yields 33,47,48 by selecting cross metathesis…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Fatty Substituted 4-methyl-2HChromen-2-one via Cross Metathesis: Potential Antioxidants and Chemotherapeutic Agents

et al. 2016

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“…(PCy 3 ) 2 (Cl) 2 Ru CHPh catalyst gave polymer with a mixture of cis and trans double bonds, 59% of trans structure. It is well known that many rutheniumbased catalysts provide predominantly trans double bonds in ROMP of other norbornenes [8,17]. Figure 3 shows the 1 H NMR spectra of monomer 3b (a) and polymer 4b (b).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of high‐T_g polymers via ROMP of oxanorbornene dicarboximides with halogen groups

Çetinkaya

Bayram

2010

Heteroatom Chemistry

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Ring-Opening Metathesis Polymerization of Coumarin-Containing Norbornene

Cited by 29 publications

References 11 publications

Synthesis and Oxygen Permeability of Polynorbornene with Tosylate Side Chain Group

Synthesis and Oxygen Permeability of Polynorbornene with Tosylate Side Chain Group

Synthesis of Novel Fatty Substituted 4-methyl-2HChromen-2-one via Cross Metathesis: Potential Antioxidants and Chemotherapeutic Agents

Synthesis of high‐T_g polymers via ROMP of oxanorbornene dicarboximides with halogen groups

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Ring-Opening Metathesis Polymerization of Coumarin-Containing Norbornene

Cited by 29 publications

References 11 publications

Synthesis and Oxygen Permeability of Polynorbornene with Tosylate Side Chain Group

Synthesis and Oxygen Permeability of Polynorbornene with Tosylate Side Chain Group

Synthesis of Novel Fatty Substituted 4-methyl-2HChromen-2-one via Cross Metathesis: Potential Antioxidants and Chemotherapeutic Agents

Synthesis of high‐Tg polymers via ROMP of oxanorbornene dicarboximides with halogen groups

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Synthesis of high‐T_g polymers via ROMP of oxanorbornene dicarboximides with halogen groups