Synthesis of Odd Generation Triazine Dendrimers Using a Divergent, Macromonomer Approach

被引：33

作者：

Lim, Jongdoo

Mintzer, Meredith A.

Perez, Lisa M.

Simanek, Eric E. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 06期

关键词：

STAGE CONVERGENT APPROACH; GROWTH APPROACH; REACTIVITY; MACROMOLECULES; CHEMISTRY; DENDRONS; POLYMERS; MELAMINE; SHAPE;

D O I：

10.1021/ol902669g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using a macromonomer, first, third, and fifth generation triazine dendrimers can be prepared using a divergent approach. The nine-step process to the fifth generation target relies on an iterative two-reactions-per-generation strategy to yield the desired material in similar to 48% overall yield. This target displays 96 surface groups. NMR spectroscopy and mass spectrometry show that exceptionally narrow polydispersity is achieved using this strategy.

引用

收藏

页码：1148 / 1151

页数：4

相关论文

共 25 条

[1] A convergent synthesis of a carbohydrate-containing dendrimer [J].

Ashton, PR ;

Boyd, SE ;

Brown, CL ;

Jayaraman, N ;

Stoddart, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07) :732-735

[2] Kilogram-scale synthesis of a second-generation dendrimer based on 1,3,5-triazine using green and industrially compatible methods with a single chromatographic step [J].

Chouai, Abdellatif ;

Simanek, Eric E. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) :2357-2366

[3] A divergent route towards single-chemical entity triazine dendrimers with opportunities for structural diversity [J].

Crampton, Hannah ;

Hollink, Emily ;

Perez, Lisa M. ;

Simanek, Eric E. .

NEW JOURNAL OF CHEMISTRY, 2007, 31 (07) :1283-1290

[4] Convergent dendrons and dendrimers:: from synthesis to applications [J].

Grayson, SM ;

Fréchet, JMJ .

CHEMICAL REVIEWS, 2001, 101 (12) :3819-3867

[5]

Hawker C. J., 1992, J CHEM SOC P1, V19, P2459

[6] PREPARATION OF POLYMERS WITH CONTROLLED MOLECULAR ARCHITECTURE - A NEW CONVERGENT APPROACH TO DENDRITIC MACROMOLECULES [J].

HAWKER, CJ ;

FRECHET, JMJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7638-7647

[7] Double-stage convergent approach for the synthesis of functionalized dendritic aliphatic polyesters based on 2,2-bis(hydroxymethyl)propionic acid [J].

Ihre, H ;

Hult, A ;

Frechet, JMJ ;

Gitsov, I .

MACROMOLECULES, 1998, 31 (13) :4061-4068

[8] Rapid synthesis of aromatic polyamide dendrimers by an orthogonal and a double-stage convergent approach [J].

Ishida, Y ;

Jikei, M ;

Kakimoto, MA .

MACROMOLECULES, 2000, 33 (09) :3202-3211

[9] Synthesis of large generation poly(propyl ether imine) (PETIM) dendrimers [J].

Jayamurugan, Govindasamy ;

Jayaraman, Narayanaswamy .

TETRAHEDRON, 2006, 62 (41) :9582-9588

[10] Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "Click" chemistry [J].

Killops, Kato L. ;

Campos, Luis M. ;

Hawker, Craig J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5062-+