Selectively Dendronized Cellulose: Synthesis and Characterization

Selectively dendronized cellulose at C-6 was synthesized homogeneously (in DMSO) and heterogeneously (in methanol) by the conversion of 6-azido-6-deoxy cellulose (degree of substitution, DS 0.75) with polyamidoamine (PAMAM) dendrons possessing an ethynyl focal moiety via the copper-catalyzed Huisgen reaction (click reaction) under mild conditions. First to third generation of PAMAM-triazolo cellulose derivatives with DS values of up to 0.69 could be prepared, which are soluble in organic solvents (DMSO, DMF) and in water. The novel biopolymer derivatives were characterized by elemental analysis, FTIR, and NMR spectroscopic methods, showing no impurities and no conversion at the secondary positions.

[1]  T. Heinze,et al.  Novel bulky esters of cellulose. , 2007, Macromolecular bioscience.

[2]  W. Binder,et al.  ‘Click’ Chemistry in Polymer and Materials Science , 2007 .

[3]  T. Heinze,et al.  Studies on Non‐natural Deoxyammonium Cellulose , 2006 .

[4]  Jonas Hafrén,et al.  Heterogeneous ‘Organoclick’ Derivatization of Polysaccharides , 2006 .

[5]  T. Heinze,et al.  Esterification of Polysaccharides , 2006 .

[6]  Jae Wook Lee,et al.  Convergent Synthesis of Symmetrical and Unsymmetrical PAMAM Dendrimers , 2006 .

[7]  T. Heinze,et al.  Click Chemistry with Polysaccharides , 2006 .

[8]  G. Newkome,et al.  Regioselective combinatorial-type synthesis, characterization, and physical properties of dendronized cellulose , 2005 .

[9]  H. Fink,et al.  Cellulose: faszinierendes Biopolymer und nachhaltiger Rohstoff , 2005 .

[10]  Thomas Heinze,et al.  Tailored cellulose esters: synthesis and structure determination. , 2005, Biomacromolecules.

[11]  G. Newkome,et al.  Regioselective Dendritic Functionalization of Cellulose , 2004 .

[12]  T. Heinze,et al.  Novel regioselectively 6-functionalized cationic cellulose polyelectrolytes prepared via cellulose sulfonates , 2001 .

[13]  T. Heinze,et al.  Nucleophilic displacement reactions on tosyl cellulose by chiral amines , 2001 .

[14]  T. Heinze,et al.  p-Toluenesulfonyl esters in cellulose modifications : acylation of remaining hydroxyl groups , 1996 .

[15]  T. Heinze,et al.  Homogeneous synthesis of cellulose p‐toluenesulfonates in N,N‐dimethylacetamide/LiCl solvent system , 1996 .