Click Chemistry: Determining the Effect Chitosan Plays on the Physicochemical Properties of Poly(arylene ether)- based Glycopolymer for Reverse Osmosis
Board Location: #60
Discipline: Chemistry and Chemical Sciences
Subcategory: Water
Session: 2
Arianna Malon Davis - Florida Agricultural and Mechanical University
Co-Author(s): Simeon Newman, FAMU-FSU College of Engineering, Tallahassee, FL; Sanjay Kumar Devendhar Singh, Florida Agricultural and Mechanical University, Tallahassee, FL; Natalie Y. Arnett, Florida Agricultural and Mechanical University, Tallahassee, FL
Reverse osmosis (RO) is the process of purifying water by the removal of contaminants from feed water under pressure through a semi-permeable membrane. In this research two polymers, chitosan and poly(arylene ether sulfone) (PAES), which have shown good RO properties will be blended and evaluated as RO membranes. Alkyne derivatized PAES (a-PPLn PAES) prepared from alkyne phenolphthalin (a-PPLn) and difluorodiphenylsulfone (DFDPS) were synthesized by nucleophilic aromatic substitution. A poly(arylene ether sulfone) based glycopolymer were successfully prepared by copper catalyst Huisgen cycloaddition, also known as a click chemistry reaction. The overall reaction is divided into three steps: 1) preparation of ethynyl derivative of phenolphthalein-based poly arylene ether sulfone homopolymer (a-PPLn PAES) using 4,4′-dichlorodiphenyl sulfone (DCDPS) and azide phenolphthalin (a-PPLn), 2) azidation of chitosan by protecting the amine group to form 6-azido-N-phthaloylated chitosan derivative, and 3) click reaction between azide derivatized chitosan with a-PPLn PAES to form a triazole linkage. FTIR analysis of chitosan and its derivative confirmed the presence of O-H and N-H stretching vibrations at 3434 cm−1 and 3256 cm−1, respectively. Azidation of chitosan derivative was confirmed by the presence of a significant absorption band around 2112 cm−1. The coupling reaction between 6-azido-N-phthaloylated chitosan derivative with phenolphthalein-based poly arylene ether sulfone homopolymer was confirmed by the disappearance of a sharp absorption band at 2112 cm−1 (C6-N3). The water flux and salt rejection of the a-PPLn PAES/Chitosan membranes were tested using a Sterlitech CF042H cross-flow reverse osmosis (RO) system. This project was funded by NSF DMR 2122142.
Funder Acknowledgement(s): This project was funded by NSF DMR 2122142.
Faculty Advisor: Dr. Natalie Y. Arnett, natalie.arnett@famu.edu
Role: I completed the synthetization of the 6-azido-N-phthaloylated chitosan and the FTIR analysis of the product.