Helix-sense-selective radical polymerization of N-(triphenylmethyl)methacrylamides and properties of the polymers

被引：23

作者：

Hoshikawa, Naohiro ^{[1
]}

Yamamoto, Chiyo ^{[1
]}

Hotta, Yuji ^{[1
]}

Okamoto, Yoshio ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

POLYMER JOURNAL | 2006年 / 38卷 / 12期

关键词：

methacrylamide; helicity; optically active polymer; chiral recognition; isotactic polymer;

D O I：

10.1295/polymj.PJ2006087

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 [高分子化学与物理]; 080501 [材料物理与化学]; 081704 [应用化学];

摘要：

N-(Triphenylmethyl)methacrylamide (TrMAM) and N-[di(4-butylphenyl)-phenylmethyl]methacrylamide (DBuTrMAM) were polymerized using a radical initiator. The obtained poly(TrMAM) was insoluble in common organic solvents, but poly(DBuTrMAM) was soluble in chloroform and THE Both polymers were dissolved in conc. H2SO4 accompanied by cleavage of the side groups to give poly(methacrylamide) (poly(MAM)). The H-1 NMR of the polymers in D2SO4 indicated that the polymers obtained at low temperature were nearly 100% isotactic. The poly(MAM) with almost 100% isotacticity showed a crystallinity. The poly(DBuTrMAM) formed a lyotropic crystalline phase in chloroform. The radical polymerization of the monomers in the presence of various chiral additives produced optically active polymers having a prevailing helicity. The optically active poly(TrMAM) exhibited a low chiral recognition.

引用

页码：1258 / 1266

页数：9

共 51 条

[1]

Asymmetric radical polymerization of N-phenylmethacrylamides [J].

Amano, Y ;

Okamoto, Y .

POLYMER JOURNAL, 2005, 37 (08) :629-632

[2]

Helix-sense-selective free radical polymerization of N-(triphenylmethyl)methacrylamide derivatives [J].

Azam, A. K. M. Fakhrul ;

Kamigaito, Masami ;

Okamoto, Yoshio .

POLYMER JOURNAL, 2006, 38 (10) :1035-1042

[3]

CAVALLO L, 1989, POLYM COMMUN, V30, P236

[4]

TRIETHYLBORON AS AN INITIATOR FOR VINYL POLYMERIZATION [J].

FURUKAWA, J ;

TSURUTA, T ;

INOUE, S .

JOURNAL OF POLYMER SCIENCE, 1957, 26 (113) :234-236

[5]

Habaue S, 1996, ENANTIOMER, V1, P55

[6]

Stereocontrolled radical polymerization of acrylamides and methacrylamides using Lewis acids [J].

Habaue, S ;

Isobe, Y ;

Okamoto, Y .

TETRAHEDRON, 2002, 58 (41) :8205-8209

[7]

Haraue S, 2001, CHEM REC, V1, P46

[8]

DETERMINATION OF TACTICITY OF POLYMETHACRYLAMIDE BY C-13 NMR-SPECTROSCOPY [J].

HATADA, K ;

KITAYAMA, T ;

UTE, K .

POLYMER BULLETIN, 1983, 9 (4-5) :241-244

[9]

STEREOREGULAR POLYMERIZATION OF ALPHA-SUBSTITUTED ACRYLATES [J].

HATADA, K ;

KITAYAMA, T ;

UTE, K .

PROGRESS IN POLYMER SCIENCE, 1988, 13 (03) :189-276

[10]

Stereospecific radical polymerization of N-triphenylmethylmethacrylamides leading to highly isotactic helical polymers [J].

Hoshikawa, N ;

Hotta, Y ;

Okamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12380-12381

← 1 2 3 4 5 6 →