Novel Biopolymer Structures Synthesized by Dendronization of 6‐Deoxy‐6‐aminopropargyl cellulose

Abstract

Propargyl cellulose with regioselective functionalization pattern was synthesized by nucleophilic displacement reaction of 6‐O‐toluenesulfonyl ester of cellulose (degree of substitution, DS 0.58) with propargyl amine. The novel 6‐deoxy‐6‐aminopropargyl cellulose provides an excellent starting material for the selective dendronization of cellulose at position 6 via the copper‐catalyzed Huisgen reaction yielding 6‐deoxy‐6‐amino‐(4‐methyl‐[1,2,3‐triazolo]‐1‐propyl‐polyamido amine) cellulose derivatives of first‐ (DS 0.33) and second (DS 0.25) generation, which are soluble in polar aprotic solvents. The novel biopolymer derivatives were characterized by elemental analysis, FT‐IR spectroscopy, and one‐ and two dimensional NMR spectroscopy, showing no side reactions (cross‐linking) or impurities and no conversion at the secondary positions.magnified image

Polysaccharides: The “Click” Chemistry Impact

“…During the same year, a slightly different synthesis method of these dendrons cellulose was developed ( Figure 9) [19]. This time, azidopropyl-dendrons and the 6-deoxy-6-cellulose aminopropargyl (DS 0.41) facilitated modified cellulose by nucleophilic displacement of the 6-tosylcellulose (DS 0.58), using propargyl amine.…”

An Efficient and Environmentally Friendly Method for the Synthesis of Cellulose Carbamate by Microwave Heating

“…), regenerated materials (fibers, films, membranes, and sponges, among others) and other functional materials. [3][4][5][6] However, cellulose has not reached its full potential in applications because it cannot be melted into a desired form or be dissolved in a common solvent, which is attributed to its strong inter-and intramolecular hydrogen bonding. In the regenerated cellulose fiber and cellophane industries, the viscose process has long occupied the lead position, [3,7] although this process generates several environmentally hazardous byproducts, which include CS 2 , H 2 S, and heavy metals.…”

Designing syntheses of cellulose and starch derivatives with basic or cationic N‐functions: part I—cellulose derivatives

“…Another promising approach for synthesis of cationic or basic cellulose derivatives having N ‐functions is the introduction of an appropriate moiety (azide or carbon–carbon triple bond) into cellulose by S N reaction and subsequent Huisgen cycloaddition as a click reaction . Huisgen reaction is a 1,3‐dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3‐triazole.…”

“…In all reactions mentioned earlier, an azide‐containing cellulose derivative was used as a precursor. An alternative synthesis path including 1,3‐dipolar cycloaddition reactions of a cellulose derivative having triple bond with compounds bearing an azide moiety were also studied . Nucleophilic displacement reaction of cellulose tosylate with propargyl amine in polar aprotic solvents is appropriate for the regioselective introduction of the C≡C bonds at position 6 of the anhydroglucose repeating unit.…”