Synthesis of aromatic poly(ether ketone)s bearing optically active macrocycles through Suzuki coupling polymerization

被引:43
作者
Maeyama, Katsuya [1 ]
Yamashita, Kenji [2 ]
Saito, Hiromu [2 ]
Aikawa, Shunichi [3 ]
Yoshida, Yasuhiko [3 ]
机构
[1] Yamagata Univ, Grad Sch Sci & Engn, Dept Polymer Sci & Engn, Yonezawa, Yamagata 9928510, Japan
[2] Tokyo Univ Agr & Technol, Grad Sch Technol, Dept Organ & Polymer Mat Chem, Koganei, Tokyo, Japan
[3] Toyo Univ, Bionano Elect Res Ctr, Kawagoe, Saitama, Japan
关键词
aromatic poly(ether ketone)s; excellent solubility; macrocycles; Suzuki coupling polymerization; thermal stability; POLYKETONES;
D O I
10.1038/pj.2011.134
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Palladium (Pd)-catalyzed Suzuki coupling polymerization of macrocycle-bearing monomers, obtained through two-step nucleophilic aromatic substitution reactions with three types of diboric acid pinacol esters, produced aromatic poly(ether ketone)s that have optically active macrocycles composed of two 2,2'-dioxy-1,1'-binaphthyl-6,6'-diyl units and two aromatic ether ketone linkers. The macrocycle-bearing aromatic poly(ether ketone) s have excellent thermal and optical properties, that is, high glass-transition temperatures (T-g: 220-257 degrees C) and large molar rotations ([Phi](D)(25): +1906-1976 deg). In addition, polyketones have excellent solubility in typical solvents such as CHCl3 and N,N-dimethylformamide (DMF). Polymer Journal (2012) 44, 315-320; doi:10.1038/pj.2011.134; published online 11 January 2012
引用
收藏
页码:315 / 320
页数:6
相关论文
共 18 条
[1]  
CAO H, 2002, POLYM PREP-ACS, V43, P1112
[2]  
DANG G, 2003, POLYM PREP-ACS, V44, P911
[3]   PHOSPHORUS PENTOXIDE-METHANESULFONIC ACID - CONVENIENT ALTERNATIVE TO POLYPHOSPHORIC ACID [J].
EATON, PE ;
CARLSON, GR ;
LEE, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (23) :4071-4073
[4]   Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity [J].
Ema, Tadashi ;
Tanida, Daisuke ;
Sugita, Kyoko ;
Sakai, Takashi ;
Miyazawa, Ken-ichiro ;
Ohnishi, Atsushi .
ORGANIC LETTERS, 2008, 10 (12) :2365-2368
[5]   Synthesis and self-assembly of comb oligomers having rigid racemic or chiral binaphthyl macrocyclic pendant groups [J].
Liu, Na ;
Wang, Xing ;
Jin, E. ;
Chen, Chunhai ;
Zhang, Wanjin ;
Wei, Yen .
POLYMER, 2006, 47 (09) :3021-3027
[6]   Synthesis of rigid and optically active bis(binaphthyl) cyclic compounds [J].
Maeda, Shugo ;
Maeyama, Katsuya ;
Yonezawa, Noriyuki .
SYNTHETIC COMMUNICATIONS, 2007, 37 (16) :2663-2670
[7]   Synthesis of optically active aromatic poly(ether ketone)s containing 2,2′-bis (4-benzoylphenoxy)-1,1′-binaphthyl-6,6′-ene backbones [J].
Maeyama, K ;
Maeda, S ;
Ogino, K ;
Saito, H ;
Yonezawa, N .
REACTIVE & FUNCTIONAL POLYMERS, 2005, 65 (03) :229-237
[8]   Nickel complex-mediated synthesis of optically active wholly aromatic polyketones bearing 2,2′-dimethoxy-1,1′-binaphthyl-6,6′-ene units [J].
Maeyama, K ;
Ogura, K ;
Okamoto, A ;
Ogino, K ;
Saito, H ;
Yonezawa, N .
POLYMER JOURNAL, 2005, 37 (10) :736-741
[9]   Synthesis of optically active aromatic poly(ether ketone)s via nucleophilic aromatic substitution polymerization [J].
Maeyama, K ;
Hikiji, I ;
Ogura, K ;
Okamoto, A ;
Ogino, K ;
Saito, H ;
Yonezawa, N .
POLYMER JOURNAL, 2005, 37 (09) :707-710
[10]   Synthesis of wholly aromatic polyketones based on fine molecular designing [J].
Maeyama, K .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (06) :616-626