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Erschienen in: Polymer Bulletin 8/2013

01.08.2013 | Original Paper

Influence of ruthenium alkylidene complexes bearing tricyclohexylphosphine or 3-bromopyridine ligand on the properties of fluorine containing polymers

verfasst von: Sevil Çetinkaya, Taner Özker, Pembe Hülya Kaya, Emine Yaşar, Rifat Bayram

Erschienen in: Polymer Bulletin | Ausgabe 8/2013

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Abstract

The catalytic performance of ruthenium alkylidene complexes bearing tricyclohexylphosphine or 3-bromopyridine ligand in the ring opening metathesis polymerization (ROMP) of fluorine containing monomers, exo-N-4-fluorophenyl-7-oxanorbornene-5,6-dicarboximide (FPhONDI) and exo-N-4-fluorophenyl-norbornene-5,6-dicarboximide (FPhNDI) was investigated. Pure monomers were subjected to ROMP with RuCl2(PCy3)2(CHPh) (I), RuCl2(PCy3)(H2IMes)(CHPh) (II), RuCl2(3-Br-py)2(PCy3)(CHPh) (III) and RuCl2(3-Br-py)2(H2IMes)(CHPh) (IV). The polymers were fully characterized using NMR, DSC, SEM and GPC. Catalysts IIV displayed significant ROMP activity, allowing for the synthesis of the corresponding polymers with polydispersity indices (PDIs) in the range of 1.4–4.0. High molecular weight polymers (Mw up to 4.95 x105) were prepared in yields up to 90 %, depending on the initiator and monomer used.

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Literatur
1.
Zurück zum Zitat Black G, Maher D, Risse W (2003) Living ring-opening olefin metathesis polymerization. In: Grubbs RH (ed) Handbook of metathesis, vol 3. Wiley-VCH, Weinheim, pp 2–71CrossRef Black G, Maher D, Risse W (2003) Living ring-opening olefin metathesis polymerization. In: Grubbs RH (ed) Handbook of metathesis, vol 3. Wiley-VCH, Weinheim, pp 2–71CrossRef
2.
Zurück zum Zitat Ivin KJ, Mol JC (1997) Olefin metathesis and metathesis polymerization. Academic Press, New York Ivin KJ, Mol JC (1997) Olefin metathesis and metathesis polymerization. Academic Press, New York
3.
Zurück zum Zitat Bielawski CW, Grubbs RH (2007) Living ring-opening metathesis polymerization. Prog Polym Sci 32:1–29CrossRef Bielawski CW, Grubbs RH (2007) Living ring-opening metathesis polymerization. Prog Polym Sci 32:1–29CrossRef
4.
Zurück zum Zitat Smith D, Pentzer EB, Nguyen ST (2007) Bioactive and therapeutic ROMP polymers. Polym Rev 47:419–459CrossRef Smith D, Pentzer EB, Nguyen ST (2007) Bioactive and therapeutic ROMP polymers. Polym Rev 47:419–459CrossRef
5.
Zurück zum Zitat Buchmeiser MR (2000) Homogeneous ring-opening metathesis polymerization by well-defined group VI and group VIII transition metal alkylidenes: fundamentals and applications in the preparation of advanced materials. Chem Rev 100:1565–1604CrossRef Buchmeiser MR (2000) Homogeneous ring-opening metathesis polymerization by well-defined group VI and group VIII transition metal alkylidenes: fundamentals and applications in the preparation of advanced materials. Chem Rev 100:1565–1604CrossRef
6.
Zurück zum Zitat Trnka TM, Grubbs RH (2001) The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. Acc Chem Res 34:18–29CrossRef Trnka TM, Grubbs RH (2001) The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. Acc Chem Res 34:18–29CrossRef
7.
Zurück zum Zitat Furstner A (2000) Olefinmetathese und mehr. Angew Chem 112:3140–3172CrossRef Furstner A (2000) Olefinmetathese und mehr. Angew Chem 112:3140–3172CrossRef
8.
Zurück zum Zitat Grubbs RH, Chang S (1998) Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 54:4413–4450CrossRef Grubbs RH, Chang S (1998) Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 54:4413–4450CrossRef
9.
Zurück zum Zitat Nishihara Y, Izawa S, Inoue Y, Nakayama Y, Shiono T, Takagi K (2008) Synthesis, characterization, and thermal properties of ring-opening metathesis polynorbornenes and their hydrogenated derivatives bearing various ester and cyano groups. J Polym Sci Part A Polym Chem 46:3314–3325CrossRef Nishihara Y, Izawa S, Inoue Y, Nakayama Y, Shiono T, Takagi K (2008) Synthesis, characterization, and thermal properties of ring-opening metathesis polynorbornenes and their hydrogenated derivatives bearing various ester and cyano groups. J Polym Sci Part A Polym Chem 46:3314–3325CrossRef
10.
Zurück zum Zitat Love JA, Morgan JP, Trnka TM, Grubbs RH (2002) A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile. Angew Chem 114:4207–4209CrossRef Love JA, Morgan JP, Trnka TM, Grubbs RH (2002) A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile. Angew Chem 114:4207–4209CrossRef
11.
Zurück zum Zitat Drozdzak R, Allaert B, Ledoux N, Dragutan I, Dragutan V, Verpoort F (2005) Ruthenium complexes bearing bidentate Schiff base ligands as efficient catalysts for organic and polymer syntheses. Coord Chem Rev 249:3055–3074CrossRef Drozdzak R, Allaert B, Ledoux N, Dragutan I, Dragutan V, Verpoort F (2005) Ruthenium complexes bearing bidentate Schiff base ligands as efficient catalysts for organic and polymer syntheses. Coord Chem Rev 249:3055–3074CrossRef
12.
Zurück zum Zitat Choi TL, Grubbs RH (2003) Controlled living ring-opening-metathesis polymerization by a fast-initiating ruthenium catalyst. Angew Chem 115:1785–1788CrossRef Choi TL, Grubbs RH (2003) Controlled living ring-opening-metathesis polymerization by a fast-initiating ruthenium catalyst. Angew Chem 115:1785–1788CrossRef
13.
Zurück zum Zitat Mutlu H, Meier MAR (2010) Ring-opening metathesis polymerization of fatty acid derived monomers. J Polym Sci Part A Polym Chem 48:5899–5906CrossRef Mutlu H, Meier MAR (2010) Ring-opening metathesis polymerization of fatty acid derived monomers. J Polym Sci Part A Polym Chem 48:5899–5906CrossRef
14.
Zurück zum Zitat Vargas J, Sánchez E, Tlenkopatchev MA (2004) Ring-opening metathesis polymerization (ROMP) of N-cycloalkyl-7-oxanorbornene dicarboximides by well-defined ruthenium initiators. Eur Polym J 40:1325–1335CrossRef Vargas J, Sánchez E, Tlenkopatchev MA (2004) Ring-opening metathesis polymerization (ROMP) of N-cycloalkyl-7-oxanorbornene dicarboximides by well-defined ruthenium initiators. Eur Polym J 40:1325–1335CrossRef
15.
Zurück zum Zitat Bazen GC, Schrock RR, Cho HN, Gibson VC (1991) Polymerization of functionalized norbornenes employing Mo(CH-t-Bu)(NAr)(O-t-Bu)2 as the initiator. Macromolecules 24:4495–4502CrossRef Bazen GC, Schrock RR, Cho HN, Gibson VC (1991) Polymerization of functionalized norbornenes employing Mo(CH-t-Bu)(NAr)(O-t-Bu)2 as the initiator. Macromolecules 24:4495–4502CrossRef
16.
Zurück zum Zitat Asrar J, Hurlbut JB (1993) Synthesis, rheology, and physical properties of a metathesis polymer. J Appl Polym Sci 50:1727–1732CrossRef Asrar J, Hurlbut JB (1993) Synthesis, rheology, and physical properties of a metathesis polymer. J Appl Polym Sci 50:1727–1732CrossRef
17.
Zurück zum Zitat Asrar J (1992) Metathesis polymerization of N-phenylnorbornenedicarboximide. Macromolecules 25:5150–5156CrossRef Asrar J (1992) Metathesis polymerization of N-phenylnorbornenedicarboximide. Macromolecules 25:5150–5156CrossRef
18.
Zurück zum Zitat Asrar J (1994) High-temperature metathesis polymers: structure-property relationships. Macromolecules 27:4036–4042CrossRef Asrar J (1994) High-temperature metathesis polymers: structure-property relationships. Macromolecules 27:4036–4042CrossRef
19.
Zurück zum Zitat Diaz K, Vargas J, Castillo LFD, Tlenkopatchev MA, Aguilar-Vega M (2005) Polynorbornene dicarboximides with cyclic pendant groups: synthesis and gas transport properties. Macromol Chem Phys 206:2316–2322CrossRef Diaz K, Vargas J, Castillo LFD, Tlenkopatchev MA, Aguilar-Vega M (2005) Polynorbornene dicarboximides with cyclic pendant groups: synthesis and gas transport properties. Macromol Chem Phys 206:2316–2322CrossRef
20.
Zurück zum Zitat Contreras AP, Tlenkopatchev MA, Lopez-Gonzalez MM, Riande E (2002) Synthesis and gas transport properties of new high glass transition temperature ring-opened polynorbornenes. Macromolecules 35:4677–4684CrossRef Contreras AP, Tlenkopatchev MA, Lopez-Gonzalez MM, Riande E (2002) Synthesis and gas transport properties of new high glass transition temperature ring-opened polynorbornenes. Macromolecules 35:4677–4684CrossRef
21.
Zurück zum Zitat Garbow JR, Goetz J, Asrar J (1998) Polymers of methyl-substituted N-phenylnorbornene-5,6-dicarboximide: characterization of structure and dynamics. Macromolecules 31:3925–3930CrossRef Garbow JR, Goetz J, Asrar J (1998) Polymers of methyl-substituted N-phenylnorbornene-5,6-dicarboximide: characterization of structure and dynamics. Macromolecules 31:3925–3930CrossRef
22.
Zurück zum Zitat Contreras AP, Cerda AM, Tlenkopatchev MA (2002) Synthesis of high-Tg polymers by ring-opening metathesis polymerization of N-cycloalkylnorbornene dicarboximide. Macromol Chem Phys 203:1811–1818CrossRef Contreras AP, Cerda AM, Tlenkopatchev MA (2002) Synthesis of high-Tg polymers by ring-opening metathesis polymerization of N-cycloalkylnorbornene dicarboximide. Macromol Chem Phys 203:1811–1818CrossRef
23.
Zurück zum Zitat Çetinkaya S, Bayram R (2010) Synthesis of high-Tg polymers via ROMP of oxanorbornene dicarboximides with halogen groups. Heteroatom Chem 21:36–43 Çetinkaya S, Bayram R (2010) Synthesis of high-Tg polymers via ROMP of oxanorbornene dicarboximides with halogen groups. Heteroatom Chem 21:36–43
24.
Zurück zum Zitat Çetinkaya S (2010) Development and characterization of lithium salts doped nanoconductive ROMP polymers. Synth Met 160:978–983CrossRef Çetinkaya S (2010) Development and characterization of lithium salts doped nanoconductive ROMP polymers. Synth Met 160:978–983CrossRef
25.
Zurück zum Zitat Çetinkaya S, Özker T (2010) Homogeneous catalysis in the preparation of new carboximide-based thermoplastic polymers. Appl Catal A Gen 382:85–89CrossRef Çetinkaya S, Özker T (2010) Homogeneous catalysis in the preparation of new carboximide-based thermoplastic polymers. Appl Catal A Gen 382:85–89CrossRef
26.
Zurück zum Zitat Çetinkaya S, Özker T, Bayram R (2011) Application of well-defined ruthenium alkylidenes to the ROMP of norbornene derivatives: methoxyphenyl-substituted polynorbornene dicarboximides. Appl Catal A Gen 393:24–28CrossRef Çetinkaya S, Özker T, Bayram R (2011) Application of well-defined ruthenium alkylidenes to the ROMP of norbornene derivatives: methoxyphenyl-substituted polynorbornene dicarboximides. Appl Catal A Gen 393:24–28CrossRef
27.
Zurück zum Zitat Feast WJ, Blackmore PM (1988) Stereoregular fluoropolymers: 6. The ring-opening polymerization of N-pentafluorophenylbicyclo[2.2.1]hept-5-ene-2,3-dicarboximide. J Fluor Chem 40:331–347CrossRef Feast WJ, Blackmore PM (1988) Stereoregular fluoropolymers: 6. The ring-opening polymerization of N-pentafluorophenylbicyclo[2.2.1]hept-5-ene-2,3-dicarboximide. J Fluor Chem 40:331–347CrossRef
28.
Zurück zum Zitat Feast WJ, Gimeno M, Khosravi E (2003) Approaches to highly polar polymers with low glass transition temperatures. 1. fluorinated polymers via a combination of ring-opening metathesis polymerization and hydrogenation. Polymer 44:6111–6121CrossRef Feast WJ, Gimeno M, Khosravi E (2003) Approaches to highly polar polymers with low glass transition temperatures. 1. fluorinated polymers via a combination of ring-opening metathesis polymerization and hydrogenation. Polymer 44:6111–6121CrossRef
29.
Zurück zum Zitat Feast WJ, Gimeno M, Khosravi E (2004) Approaches to highly polar polymers with low glass transition temperatures: 2. fluorinated polymers via ring-opening metathesis copolymerisation and hydrogenation. J Mol Catal A Chem 213:9–14CrossRef Feast WJ, Gimeno M, Khosravi E (2004) Approaches to highly polar polymers with low glass transition temperatures: 2. fluorinated polymers via ring-opening metathesis copolymerisation and hydrogenation. J Mol Catal A Chem 213:9–14CrossRef
30.
Zurück zum Zitat Santiago AA, Vargas J, Fomine S, Gavino R, Tlenkopatchev MA (2010) Polynorbornene with pentafluorophenyl imide side chain groups: synthesis and sulfonation. J Polym Sci Part A Polym Chem 48:2925–2933CrossRef Santiago AA, Vargas J, Fomine S, Gavino R, Tlenkopatchev MA (2010) Polynorbornene with pentafluorophenyl imide side chain groups: synthesis and sulfonation. J Polym Sci Part A Polym Chem 48:2925–2933CrossRef
31.
Zurück zum Zitat Vargas J, Martinez A, Santiago AA, Tlenkopatchev MA (2008) Synthesis of new fluorine containing ring-opened polynorbornene dicarboximides using ruthenium alkylidene catalysts. Polym Bull 61:689–697CrossRef Vargas J, Martinez A, Santiago AA, Tlenkopatchev MA (2008) Synthesis of new fluorine containing ring-opened polynorbornene dicarboximides using ruthenium alkylidene catalysts. Polym Bull 61:689–697CrossRef
32.
Zurück zum Zitat Santiago AA, Vargas J, Gavino R, Cerda AM, Tlenkopatchev MA (2007) Synthesis and ring-opening metathesis polymerization of new oxanorbornene dicarboximides with fluorine pendant groups. Macromol Chem Phys 208:1085–1092CrossRef Santiago AA, Vargas J, Gavino R, Cerda AM, Tlenkopatchev MA (2007) Synthesis and ring-opening metathesis polymerization of new oxanorbornene dicarboximides with fluorine pendant groups. Macromol Chem Phys 208:1085–1092CrossRef
33.
Zurück zum Zitat Love JA, Morgan JP, Trnka TM, Grubbs RH (2002) A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile. Angew Chem Int Ed 41:4035–4037CrossRef Love JA, Morgan JP, Trnka TM, Grubbs RH (2002) A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile. Angew Chem Int Ed 41:4035–4037CrossRef
34.
Zurück zum Zitat Deng LP, Liu FM, Wang HY (2005) 1,3-Dipolar cycloaddition reaction: synthesis of novel 5,6-dehydronorcantharidin derivatives of substituted aromatic amines with potential antitumor activities. J Heterocycl Chem 42:13–18CrossRef Deng LP, Liu FM, Wang HY (2005) 1,3-Dipolar cycloaddition reaction: synthesis of novel 5,6-dehydronorcantharidin derivatives of substituted aromatic amines with potential antitumor activities. J Heterocycl Chem 42:13–18CrossRef
Metadaten
Titel
Influence of ruthenium alkylidene complexes bearing tricyclohexylphosphine or 3-bromopyridine ligand on the properties of fluorine containing polymers
verfasst von
Sevil Çetinkaya
Taner Özker
Pembe Hülya Kaya
Emine Yaşar
Rifat Bayram
Publikationsdatum
01.08.2013
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 8/2013
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-013-0960-x

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