Studies on the molecular flexibility of novel dendronized carboxymethyl cellulose derivatives

Abstract

Water soluble deoxy-azido cellulose derivatives were synthesized by heterogeneous carboxymethylation, applying 2-propanol/aqueous NaOH as slurry medium. The novel,

Polysaccharides: The “Click” Chemistry Impact

“…To facilitate the solubilization of dendronized cellulose in water, Heinze and colleagues published works in 2009 showing new compounds obtained from the 6-deoxy-6-azidocellulose [17]. Water-soluble deoxy-azidocellulose derivatives were synthesized by heterogeneous carboxymethylation, applying 2-propanol/aqueous NaOH as slurry medium ( Figure 10).…”

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 subsequent years, the research was focused on the synthesis of various innovative denderimers having triazole‐spacers . Dendritic structures can be introduced by either homogeneous (in DMSO or ionic liquids) or heterogeneous (in CH 3 OH) conversion of 6‐deoxy‐6‐azido cellulose with propargyl‐PAMAM dendrons from first to third generation applying the copper‐catalyzed Huisgen reaction, yielding pure and highly functionalized products modified at the primary position of the cellulose macromolecule only (Scheme ).…”

“…The heterogeneous conversion of deoxy‐azido cellulose with sodium monochloroacetate in the presence of aqueous NaOH applying 2‐propanol as slurry medium leads to water‐soluble carboxymethyl deoxy‐azido cellulose. This novel biopolymer derivative provides an appropriate starting material for the selective dendronization via the copper‐catalyzed Huisgen reaction resulting in water‐soluble carboxymethyl 6‐deoxy‐(1‐ N ‐[1,2,3‐triazolo]‐4‐polyamidoamine) celluloses from first to third generation (Scheme ) …”

“…Synthesis of carboxymethyl 6‐deoxy‐(1‐ N ‐[1,2,3‐triazolo]‐4‐polyamidoamine) cellulose of first generation ( 13 ) via homogeneous conversion of carboxymethyl 6‐deoxy‐6‐azidocellulose ( 12 , DS Azide 0.81, DS CM 1.25) with first generation of propargyl‐polyamidoamine dendron ( 10 ) . This figure is available in colour online at wileyonlinelibrary.com/journal/pat…”