Ruthenium quinoline and quinoxaline complexes: Thermally triggered initiators for ring opening metathesis polymerization

被引:64
作者
Gstrein, Xaver
Burtscher, Daniel
Szadkowska, Anna
Barbasiewicz, Michal
Stelzer, Franz
Grela, Karol
Slugovc, Christian
机构
[1] Graz Univ Technol, ICTOS, Inst Chem & Technol Organ Mat, A-8010 Graz, Austria
[2] Polymer Competence Ctr Leoben GmbH, A-8700 Leoben, Austria
[3] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
关键词
initiators; metathesis; ROMP; ruthenium;
D O I
10.1002/pola.22083
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The usage of four ruthenium carbene complexes initially described as ring closing metathesis catalysts as Ring Opening Metathesis Polymerization (ROMP) initiators for a set of representative liquid monomers at elevated temperatures was investigated. Initiators and the monomers and a mixture of ethyl ester and ethyl ester were prepared. Other chemicals were obtained from commercial sources and used without further purification. The solvent residual peak of CDCl 3 and acetone-d6 were used for referencing the NMR spectra. The reaction was quenched by adding water (50 mL) and sodium hydroxide solution (35%, 10 mL). A voluminous white precipitate was formed that was filtered off and the solution was concentrated. It was observed that through modification of the chelating carbene ligand and the stereochemistry of the initiator a tuning of the polymerization activity could be obtained.
引用
收藏
页码:3494 / 3500
页数:7
相关论文
共 35 条
[1]  
Armarego W.L. F., 1996, PURIFICATION LAB CHE, V4th
[2]   Structure and activity peculiarities of ruthenium quinoline and quinoxaline complexes: Novel metathesis catalysts [J].
Barbasiewicz, Michal ;
Szadkowska, Anna ;
Bujok, Robert ;
Grela, Karol .
ORGANOMETALLICS, 2006, 25 (15) :3599-3604
[3]   The isomerization equilibrium between cis and trans chloride ruthenium olefin metathesis catalysts from quantum mechanics calculations [J].
Benitez, D ;
Goddard, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12218-12219
[4]   The chemistry of acrylonitrile. i. Cyanoethylation of active methylene groups [J].
Bruson, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2457-2461
[5]   Peculiarities of the reaction of (SPY-5-34)-dichloro-(κ2(C,O-2-formylbenzylidene)(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) ruthenium with potassium hydridotris(pyrazolyl)borate [J].
Burtscher, Daniel ;
Perner, Bernhard ;
Mereiter, Kurt ;
Slugovc, Christian .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) :5423-5430
[6]   Contact metathesis polymerization (CMP) [J].
Caster, KC ;
Tokas, EF ;
Keck, CG ;
Hontz, ME .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 190 (1-2) :65-77
[7]   Synthesis and characterization of new ruthenium-based olefin metathesis catalysts coordinated with bidentate Schiff-base ligands [J].
Chang, S ;
Jones, L ;
Wang, CM ;
Henling, LM ;
Grubbs, RH .
ORGANOMETALLICS, 1998, 17 (16) :3460-3465
[8]   Activity of a new class of ruthenium based ring-closing metathesis and ring-opening metathesis polymerization catalysts coordinated with a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and a Schiff base ligand [J].
De Clercq, B ;
Verpoort, F .
TETRAHEDRON LETTERS, 2002, 43 (50) :9101-9104
[9]  
Delaude L, 2002, ADV SYNTH CATAL, V344, P749, DOI 10.1002/1615-4169(200208)344:6/7<749::AID-ADSC749>3.0.CO
[10]  
2-T