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Published:20 April 2008,
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DANG Jingya, CHEN Fengxiang, HAN Huijing, HE Xiaohua, ZHANG Yiqun, XIE Meiran. Synthesis of Ionic Liquid-Supported Ruthenium Complex and Ring-Opening Metathesis Polymerization of Cycloolefin. [J]. Acta Polymerica Sinica (4):343-349(2008)
DANG Jingya, CHEN Fengxiang, HAN Huijing, HE Xiaohua, ZHANG Yiqun, XIE Meiran. Synthesis of Ionic Liquid-Supported Ruthenium Complex and Ring-Opening Metathesis Polymerization of Cycloolefin. [J]. Acta Polymerica Sinica (4):343-349(2008) DOI: 10.3724/SP.J.1105.2008.00343.
设计合成了含离子液体的吡啶配体1
2-二甲基-3-乙氧基吡啶六氟磷酸盐咪唑离子液体,在丙酮∶石油醚=3∶1的混合溶剂制备了含咪唑的离子液体.该离子液体可以做配体与Grubbs第二代催化剂反应,制备离子液体负载的钌催化剂,利用(1H
13C
31P)-NMR、元素分析等方法对合成的化合物和催化剂进行表征,催化剂中与钌连接的苯亚甲基上氢(RuH—Ph)的振动峰由原来第二代催化剂的 δ=19.2移至 δ=16.27,在 δ =-143.3处只出现PF-6中磷的信号峰,PCy3的信号消失,表明PCy3已经被置换完全,得到了新的催化剂.通过ICP测定含吡啶配体的离子液体负载的催化剂在混合物中的含量为14 wt%.该催化剂在丙酮、甲醇、咪唑类离子液体等极性溶剂中易于溶解,解决了Grubbs催化剂在离子液体中不溶解的问题,实现了在纯离子液体中均相ROMP反应.考察了催化剂对不同极性单体在离子液体[BMIm]BF4中的开环易位聚合反应,非极性的环辛烯、含有中等极性取代基的5-羟基环辛烯单体以及含强极性取代基的5-腈基-2-降冰片烯单体的转化率分别为96%、73%和51.7%.利用凝胶渗透色谱(GPC)测定了聚合物的分子量及分子量分布.
Ring-opening metathesis polymerization (ROMP) is a widespread tool for synthesizing well-defined and highly functionalized polymers.The catalyst is an important factor which affects the ROMP of monomers.It is well-known that the ruthenium-based Grubbs’catalysts have good solubility in non-polar solvents such as CH2Cl2
benzene and toluene
but their solubility in polar solvents such as alcohol
acetone and ionic liquid was very poor
which limited their applications for ROMP in polar solvents.In this paper
an imidazolium saltsupported ruthenium catalyst was synthesized
and its catalytic performance for ROMP of polar or nonpolar cycloolefinic monomers in ionic liquid [BMIm]BF4 was investigated.A novel pyridyl ligand 2
3-dimethyl-1-2-(4-pyridyloxy)ethyl] imidazolium hexafluorophosphate (4) was initially designed and synthesized
and its single crystal was obtained.The crystal is monoclinic with the parameters as follow: P21/c
a=1.2469(5) nm
b = 1.6470(7) nm
c=0.7943(3) nm
β=106.691(5)°
V=1.5625(11) nm3.The pyridyl ligand was then used to coordinate with the second generation Grubbs’catalyst to get the first example of the ruthenium catalyst supported by imidazolium saltcontained pyridyl ligand (IL-cat 5).The characterization of the synthesized ligand and the catalyst was carried out by NMR
ICP and elemental analysis.In 1H-NMR spectroscopy
the signal of the benzylidene proton shifts from δH=19.2 in the second generation Grubbs’catalyst to δH=16.3 in the novel catalyst IL-cat 5.In 31P-NMR spectroscopy
the signal of PF-6 in pyridyl ligand was observed at δP=-143.3
while δP=36.6 for PCy3 group was disappeared
which demonstrated the group of PCy3 was replaced by the pyridyl ligand completely.The content of IL-cat 5 in the mixture of prepared catalyst contained excess 4 was 14 wt% tested by ICP method.As expected
the novel catalyst IL-cat 5 is soluable in polar solvents including methanol acetone
and ionic liquid
thus ROMP in pure ionic liquid could be carried out conveniently.The ROMP of three different cycloolefins
i.e.nonpolar cyclooctene (monomer 1)
medium polar 5-hydroxy-1-cyclooctene (monomer 2)
and especially the strong polar monomer 5-norbornene-2-carbonitrile (monomer 3)
was explored in ionic liquid [BMIm]BF4.The polymerizations of the three monomers catalyzed by catalyst IL-cat 5 processed successfully
and the conversion reached up to 96.0%
73.0%
and 51.7% for monomer 1
monomer 2
and monomer 3 under conventional conditions
respectively.It was worth noting that the value of 51.7% for cyano group (—CN) contained monomer 3 was reasonably high
which is surprisingly much larger than that using the pyridine coordinated second generation Grubbs’catalyst for the same monomer in [BDMIm]PF6 as reported in published literature.The results strongly confirmed that ROMP could be undertaken readily for all functionalized monomers using ruthenium catalyst coordinated with imidazolium saltcontained pyridyl ligand in [BMIm]BF4
and fortunately Grubbs’catalyst was actually not poisoned in this imidazolium ionic liquid medium without —CH3 group in 2-position of imidazolyl ring.The molecular weights of polymers were measured by GPC
which were nearly in according with the calculated ones.
开环易位聚合吡啶基配体离子液体负载钌催化剂极性单体
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