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A Novel Initiator Containing Alkyne Group for the Polymerization of 2-Ethyl-2-oxazoline
Muhammad Waqas Ali,Ya-ting Gao,Muhammad Siddiq,Xiao-dong Ye*
Author NameAffiliationE-mail
Muhammad Waqas Ali Hefei National Laboratory for Physical Sciences at the Microscale, Department of Chemical Physics, University of Science and Technology of China, Hefei 230026, China  
Ya-ting Gao Hefei National Laboratory for Physical Sciences at the Microscale, Department of Chemical Physics, University of Science and Technology of China, Hefei 230026, China  
Muhammad Siddiq Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan  
Xiao-dong Ye* Hefei National Laboratory for Physical Sciences at the Microscale, Department of Chemical Physics, University of Science and Technology of China, Hefei 230026, China;CAS Key Laboratory of Soft Matter Chemistry, University of Science and Technology of China, Hefei 230026, China xdye@ustc.edu.cn 
Abstract:
A novel trifunctional initiator with one alkyne and two trifluoromethanesulfonate moieties was synthesized from a protected alcohol 5-hydroxyl-2-phenyl-1, 3-dioxane. The alkyne functionalized intermediate with two protected alcohol groups was synthesized by reacting with propargyl bromide. The alcohol groups were cleaved using a mixture of tetrahydrofuran and hydrochloric acid aqueous solution. In the last step the initiator was synthesized using triflic anhydride in carbon tetrachloride. The initiator was characterized by 1H NMR and used for the polymerization of 2-ethyl-2-oxazoline which gives polymers with narrow distribution. For comparison a similar initiator with two tosylates was prepared and used for the polymerization of the monomer 2-ethyl-2-oxazoline, the resulting product has a wide molecular weight distribution and most of the initiator remains unreacted after 24 h which may be due to the steric hindrance between the two tosylate groups. To further explore the steric hindrance phenomenon, a linear tosylate initiator was synthesized, but still some of the initiator remains unreacted, illustrating that both steric hindrance and electrophilic balance affect the efficiency of the cationic ring-opening polymerization. All of the polymers were characterized in detail by using 1H NMR, matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy, and size exclusion chromatography to confirm the purity and distribution of the polymers.
Key words:  Electrophile  2-Ethyl-2-oxazoline  Steric hindrance  Triflate
FundProject:
一种新型含炔基的聚合2-乙基-2-噁唑啉引发剂的合成
Muhammad Waqas Ali,高亚婷,Muhammad Siddiq,叶晓东*
摘要:
关键词:  
DOI:10.1063/1674-0068/31/cjcp1709171
分类号: