SYNTHESIS OF MIDDLE-CHAIN CARBOXYL- AND PRIMARY AMINE-FUNCTIONALIZED POLYSTYRENES USING ANIONIC POLYMERIZATION TECHNIQUES

 
 
 
 

SYNTHESIS OF MIDDLE-CHAIN CARBOXYL- AND PRIMARY AMINE-FUNCTIONALIZED POLYSTYRENES USING ANIONIC POLYMERIZATION TECHNIQUES

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Title: SYNTHESIS OF MIDDLE-CHAIN CARBOXYL- AND PRIMARY AMINE-FUNCTIONALIZED POLYSTYRENES USING ANIONIC POLYMERIZATION TECHNIQUES
Author: Sen, Mustafa Yasin
Description: Middle-chain, carboxyl-functionalized polystyrene was synthesized by the coupling of poly(styryl)lithium with a PDDPE-polystyrene macromonomer followed by the carbonation of living chain ends using gaseous carbon dioxide. The effect of chain-end structure on carbonation reactions was also investigated. The resulting carboxyl-functionalized polystyrene was free of dimeric ketone and trimeric alcohol, regardless of reaction conditions and quantitative carboxylation of these 1,1-diphenylalkyllithiums was accomplished. Middle-chain, primary amine-functionalized polystyrenes were synthesized by the chemical modification of anionically prepared, middle-chain, alkyl chloride-functionalized polystyrenes. The chloro functionality was introduced into the middle of a polystyrene chain by the reaction of 2-(chloroethyl)methyl dichlorosilane with two moles of poly(styryl)lithium. It was determined that the living poly(styryl) anions reacted chemoselectively at the electrophilic silicon atom. The presence of primary amine group was confirmed by MALDI-TOF mass spectroscopy. The polymer exhibited a relatively narrow molecular weight distribution (Mw/Mn=1.06) by SEC analyis after derivatizing the amine groups using trichloroacetyl isocyanate.
Permanent Link: http://rave.ohiolink.edu/etdc/view?acc_num=akron1132533104
http://hdl.handle.net/2374.OX/3529
Date: 2005

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