Alkene Metathesis - A Tool for the Synthesis of Conjugated Polymers

被引:42
作者
Bunz, Uwe H. F. [1 ]
Maeker, Dominic [1 ]
Porz, Michael [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
alkenes; conjugated polymers; metathesis reaction; polyparaphenylenevinylene (PPV); RING-OPENING METATHESIS; ACYCLIC DIENE METATHESIS; ALL-TRANS OLIGOMERS; OLEFIN-METATHESIS; HECK REACTION; POLYMERIZATION; POLYACETYLENE; MOLYBDENUM; ADMET; POLY(P-PHENYLENEETHYNYLENE)S;
D O I
10.1002/marc.201200001
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Alkene metathesis is a superb methodology. We report the progress using alkene metathesis in the synthesis of polymeric organic semiconductors. Three classes of polymers have been synthesized using acyclic diene metathesis (ADMET) or ring opening metathesis polymerization (ROMP), viz., poly(acetylene)s (PA), poly(arylene-vinylene)s (PAV), and organometallic polymers. For PAs, ROMP of cyclooctatetraenes is best, whereas for PAV, both ADMET and indirect and direct ROMP are viable. Metathesis performs flawlessly with the correct monomers, as molybdenum and particularly the robust Ru carbenes demonstrate. When performing ROMP, one is often rewarded with structurally uniform polymers that can display very low polydispersities. Overall, metathesis is a powerful tool for the preparation of semiconducting polymers.
引用
收藏
页码:886 / 910
页数:25
相关论文
共 129 条
[1]   Metathesis Reactions of Carbohydrates: Recent Highlights in Cross-Metathesis [J].
Aljarilla, Ana ;
Cristobal Lopez, J. ;
Plumet, Joaquin .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) :6123-6143
[2]   Organic semiconductors for solution-processable field-effect transistors (OFETs) [J].
Allard, Sybille ;
Forster, Michael ;
Souharce, Benjamin ;
Thiem, Heiko ;
Scherf, Ullrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4070-4098
[3]   ROMPing to Nobel success [J].
不详 .
NATURE MATERIALS, 2005, 4 (12) :877-877
[4]   Recent advances in ADMET polymerization [J].
Baughman, TW ;
Wagener, KB .
METATHESIS POLYMERIZATION, 2005, 176 :1-42
[5]   Encapsulation of emissive polymers within a fluorinated matrix [J].
Bazan, GC ;
Renak, ML ;
Sun, BJ .
MACROMOLECULES, 1996, 29 (03) :1085-1087
[6]   New insights into the microstructure of GILCH-polymerized PPVs [J].
Becker, H ;
Spreitzer, H ;
Ibrom, K ;
Kreuder, W .
MACROMOLECULES, 1999, 32 (15) :4925-4932
[7]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[8]   Living ring-opening metathesis polymerization [J].
Bielawski, Christopher W. ;
Grubbs, Robert H. .
PROGRESS IN POLYMER SCIENCE, 2007, 32 (01) :1-29
[9]   A low-bandgap poly(2,7-carbazole) derivative for use in high-performance solar cells [J].
Blouin, Nicolas ;
Michaud, Alexandre ;
Leclerc, Mario .
ADVANCED MATERIALS, 2007, 19 (17) :2295-+
[10]   Polycyclic aromatic hydrocarbons by ring-closing metathesis [J].
Bonifacio, MC ;
Robertson, CR ;
Jung, JY ;
King, BT .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8522-8526