Water soluble photoactive cellulose derivatives: synthesis and characterization of mixed 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetic acid–(3-carboxypropyl)trimethylammonium chloride esters of cellulose

Abstract

Photoactive derivatives of cellulose were prepared by a mild esterification of the biopolymer with 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetic acid via the activation of the carboxylic acid with N,N 0 -carbonyldiimidazole. Subsequently, modification with the cationic carboxylic acid (3-carboxypropyl)trimethylammonium chloride was carried out. Thus, water soluble polyelectrolytes decorated with high amounts of photochemically active chromene moieties were obtained. The structures of the novel polysaccharide esters and the polyelectrolytes were evaluated by means of NMR and IR spectroscopy. Moreover, the light triggered photodimerization of the chromene moieties of the photoactive polyelectrolytes was studied by means of UV-Vis spectroscopy in the dissolved state. The photochemistry observed may be used to control the properties of the new polysaccharide derivatives and are thus of interest in the design of smart materials.

Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass

“…Besides their traditional applications as additives in the food industry, in coatings, printing, cosmetic, textile, and in the pharmaceuticals industry, new cellulose derivatives have also been investigated for their applications, such as drug delivery systems [140], in chiral separation and recognition [141], as photoactive materials [142], as antioxidant agents [143], in memory of electronic devices [144], and graft copolymers [145].…”

Functional nanomaterials through esterification of cellulose: a review of chemistry and application

“…8c). Wondraczek et al (2012) decorated the cellulose with high amounts of photochemically active chromene moieties after the homogeneous reactions with of 2-[(4-methyl-2-oxo-2Hchromen-7-yl)oxy]acetic acid and cationic (3-carboxypropyl) trimethylammonium chloride via activation with CDI. The obtained water soluble photoactive cellulose-based polyelectrolytes are of interest for the design of smart materials.…”

Photocontrol of Mechanical Properties of Pulp Fibers and Fiber‐to‐Fiber Bonds via Self‐Assembled Polysaccharide Derivatives

“…Eucalyptus unrefined bleached Kraft pulp was purchased from Botnia (Kaskö). 2‐[(4‐methyl‐2‐oxo‐2H‐chromen‐7‐yl)oxy]acetic acid‐(3‐carboxypropyl)trimethylammonium chloride ester of cellulose was synthesized as described elsewhere . Molecular weight of the applied derivative was 114 400 g mol −1 and degree of polymerization was 384.…”

“…The adsorption does not require harsh conditions and specific facilities and, therefore, can be easily carried out in the existing facilities of pulp and paper mills. Furthermore, the well‐developed field of polysaccharide chemistry allows the preparation of advanced multifunctional derivatives, e.g., decorated with both stimuli‐responsive‐ and ionic functional groups . Thus, polyelectrolytes tailored according to the needs of the desired application yield, for example, fiber‐based stimuli‐responsive materials.…”

“…Furthermore, the well-developed field of polysaccharide chemistry allows the preparation of advanced multifunctional derivatives, e.g., decorated with both stimuli-responsive-and ionic functional groups. [16] Thus, polyelectrolytes tailored according to the needs of the desired application yield, for example, fiber-based stimuli-responsive materials. Additionally, the adsorption is very well controllable and thus only small amounts of highly engineered polysaccharide derivatives are needed to achieve a particular functionality while preserving structure of fibers.…”