A facile one-pot synthesis of a fluorescent agarose-O-naphthylacetyl adduct with slow release properties

• Published in: Carbohydrate polymers Vol. 98; no. 1; pp. 589 - 595
• Main Authors: Kondaveeti, Stalin, Chejara, Dharmesh R., Siddhanta, A.K.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 15.10.2013; Elsevier
• Subjects: 1-Naphthylacetic acid; 4-Aminopyridine - analogs & derivatives; 4-Aminopyridine - chemistry; acetic acid; Agarose; Applied sciences; carbon; Chemical Phenomena; Chemistry Techniques, Synthetic; Delayed-Action Preparations; Dicyclohexylcarbodiimide - chemistry; ethylene glycol; Exact sciences and technology; Fluorescence; fluorescence emission spectroscopy; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fourier transform infrared spectroscopy; Hydrolysis; hydrophilicity; microwave treatment; naphthaleneacetic acid; Naphthaleneacetic Acids - chemistry; Natural polymers; nuclear magnetic resonance spectroscopy; Physicochemistry of polymers; polymers; Sepharose - chemistry; stable isotopes; Starch and polysaccharides; Sustained release property; synthesis; Temperature; Fluorescence; 1-Naphthylacetic acid; Agarose; Sustained release property; Fluorescence spectrum; Control release polymer; Temperature effect; Experimental study; Naphthalene derivatives; Esterification; Chemical modification; Fluorescent material; Aqueous medium; Preparation; pH; Oside polymer; Plant growth substance; Kinetics; Alcoholic solution; Release
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2013.06.046

•Agarose-O-naphthylacetic acid (NA-Agarose) was synthesized.•Agarose was modified by 1-naphthylacetic acid (NAA) to demonstrate new functions.•NA-Agarose exhibited strong fluorescent property.•NA-Agarose released NAA in a controlled manner under hydrolytic conditions. A microwave assisted facile synthesis of a fluorescent 6-O-naphthylacetyl agarose (NA-agarose) employing carbodiimide chemistry (dicyclohexylcarbodiimide/4-dimethylaminopyridine) has been described. NA-agarose was characterized by TGA, GPC, UV spectrophotometry, fluorescence spectroscopy, FT-IR, 1H and 13C NMR spectra, exhibiting that in NA-agarose the naphthylacetyl group was attached to the backbone of the agarose polymer. The hydrolysis of NA-agarose in heterogeneous aqueous phase showed that the 1-naphthyl acetic acid (NAA), a plant growth regulator, got released in a controlled manner, the release rate being dependent on the hydrophilicity of the polymer adduct as well as on pH and temperature. The fluorescence emission (λmax 332nm) of NA-agarose (1×10−3M) in ethylene glycol was significantly higher (ca. 82%) than that of the molar equivalent of NAA content in the product i.e. 0.08mg in 1×10−3M solution. The resulting polymer would be of potential utility as a sustained release plant growth regulator and sensory applications.