Aza-Wittig Polymerization: A Simple Method for the Synthesis of Regioregular Poly(azomethine)s

被引：16

作者：

Miyake, Junpei ^{[1
]}

Chujo, Yoshiki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Polymer Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

MACROMOLECULES | 2008年 / 41卷 / 24期

关键词：

D O I：

10.1021/ma802100c

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Fully regioregular pi-conjugated poly(azomethine)s (9a-d) were successfully synthesized via aza-Wittig polymerization from an AB monomer system. The obtained regioregular poly(azomethine)s showed moderate solubility in common organic solvents Such as CHCl3, THF, and toluene. In the UV-vis absorption spectra, polymer 9c displayed absorption maximum of the longer wavelength at 425 nm and a large red shift of 95 nm relative to the absorption maximum of the model Compound 14 (lambda(max) = 330 nm) in dilute CHCl3 Solution, indicating the extension of the pi-delocalization length of polymer 9c via the AB-type pi-conjugated poly(azomethine) backbone. In the solid state, UV-vis absorption spectra and XRD data revealed that these regioregular poly(azomethine)s have higher crystallinity values compared to those for the regiorandorn poly(azomethine)s.

引用

页码：9677 / 9682

页数：6

共 53 条

[1] Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].

Barral, Karine ;

Moorhouse, Adam D. ;

Moses, John E. .

ORGANIC LETTERS, 2007, 9 (09) :1809-1811

[2] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[3] Effect of interchain interactions on the absorption and emission of poly(3-hexylthiophene) -: art. no. 064203 [J].

Brown, PJ ;

Thomas, DS ;

Köhler, A ;

Wilson, JS ;

Kim, JS ;

Ramsdale, CM ;

Sirringhaus, H ;

Friend, RH .

PHYSICAL REVIEW B, 2003, 67 (06)

[4] THE 1ST REGIOREGULAR HEAD-TO-TAIL POLY(3-HEXYLTHIOPHENE-2,5-DIYL) AND A REGIORANDOM ISOPOLYMER - NI VS PD CATALYSIS OF 2(5)-BROMO-5(2)-(BROMOZINCIO)-3-HEXYLTHIOPHENE POLYMERIZATION [J].

CHEN, TA ;

RIEKE, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :10087-10088

[5] Phenylazomethine dendrimer complexes as novel hole-transporting materials of organic light-emitting diodes [J].

Cho, JS ;

Takanashi, K ;

Higuchi, M ;

Yamamoto, KT .

SYNTHETIC METALS, 2005, 150 (01) :79-82

[6] Main chain polymers containing banana-shaped mesogens: Synthesis and mesomorphic properties [J].

Choi, EJ ;

Ahn, JC ;

Chien, LC ;

Lec, CK ;

Zin, WC ;

Kim, DC ;

Shin, ST .

MACROMOLECULES, 2004, 37 (01) :71-78

[7] Mechanism and stereoselectivity of the aza-Wittig reaction between phosphazenes and aldehydes [J].

Cossío, FP ;

Alonso, C ;

Lecea, B ;

Ayerbe, M ;

Rubiales, G ;

Palacios, F .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) :2839-2847

[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[9] Synthesis and characterization of conjugated polyazines and polyazomethines containing the thienylene moiety and flexible hydrocarbon side chains [J].

Destri, S ;

Pasini, M ;

Pelizzi, C ;

Porzio, W ;

Predieri, G ;

Vignali, C .

MACROMOLECULES, 1999, 32 (02) :353-360

[10] Synthesis, characterization, optical spectroscopic, electronic structure, and second-order nonlinear optical (NLO) properties of a novel class of donor-acceptor bis(salicylaldiminato)nickel(II) Schiff base NLO chromophores [J].

DiBella, S ;

Fragala, I ;

Ledoux, I ;

DiazGarcia, MA ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9550-9557

← 1 2 3 4 5 6 →