双丙酮-D-半乳糖手性聚合物纳米球的合成及其手性拆分
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摘要
本论文选用6-O-p-vinylbenzyl-1,2:3,4-Di-O-isopropylidene-D-galactopyranose (VBPG)为单体:(1)通过RAFT的细乳液聚合制备了不同交联程度的手性纳米粒子P(VBPG);(2)采用ATRP法和“click”化学相结合的方法把手性P(VBPG)接枝到二氧化硅表面,得到手性杂化二氧化硅纳米粒子,并研究了所得到的这两种手性纳米粒子的手性拆分等相关性能。
主要研究内容和结果如下:
(1)选用手性的VBPG为单体,二乙烯基苯(DVB)为交联剂,偶氮二异丁腈(AIBN)为引发剂,P(VBPG)(Mn,GPC = 6200 g/mol, Mw/Mn = 1.12)为Macro-RAFT试剂,甲苯为溶剂,正十六烷(HD)为助表面活性剂,十二烷基苯磺酸钠为乳化剂进行RAFT细乳液聚合。首先在无交联剂的情况下,研究了VBPG的RAFT细乳液聚合动力学,发现所得到的P(VBPG)分子量随转化率的提高而线性增长,且聚合物分散性指数较小(PDI = 1.12~1.50),符合“活性”/可控自由基聚合特征。在交联剂存在下,研究了交联剂用量对所得到的交联P(VBPG)纳米粒子性能的影响。结果表明:纳米粒子的粒径(51-130 nm)随交联剂用量的增加呈现先增大后减小的变化趋势。用阿拉伯糖和醇氨等外消旋化合物的手性拆分实验发现:该纳米粒子不但有较好的手性拆分能力,而且还可以重复使用。
(2)以功能性的2-溴异丁酸-3-炔丁酯(BEiB)为引发剂,采用ATRP法首先合成了三种含末端炔基不同链长的手性聚合链P(VBPG)。然后,使用“click”化学方法成功地将该聚合链接枝到含有叠氮的二氧化硅的表面,并考察了三种不同链长二氧化硅有机/无机杂化纳米粒子对酒石酸和醇胺等外消旋体手性拆分实验。发现该纳米粒子同样具有很好的手性拆分性能。最后考察了该手性杂化粒子在手性柱中作固定相进行HPLC手性拆分,实验发现该杂化粒子作为固定相能够对外削旋扁桃酸达到基线分离。
In this thesis, 6-O-p-vinylbenzyl-1,2:3,4-Di-O-isopropylidene-D-galactopyranose (VBPG) was selected as the monomer: (1) various cross-linked chiral nanoparticles were prepared by RAFT miniemulsion polymerization with different amounts of cross-linker, and (2) grafting chiral P(VBPG) chains to the silica surface by the combination ATRP and "click" chemistry method, to obtain chiral hybrid silica nanoparticles. And then studied the chiral separation and other related properties of the two kinds of nanoparticles.
The results were shown as follows:
1. VBPG was selected as the monomer, divinyl benzene (DVB) as the cross-linker if used, 2,2'-azobisisobutyronitrile (AIBN) as the initiator, P(VBPG) (Mn,GPC = 6200 g/mol, Mw/Mn = 1.12) as the Macro-RAFT agent, n-hexadecane (HD) as the co-emulsifier, toluene as the solvent, sodium dodecyl benzene sulfonate as the emulsifier for the RAFT miniemulsion polymerization. Firstly, the kinetics of RAFT miniemulsion polymerization was studied without cross-linker. The results showed P(VBPG) molecular weight increased with conversion and the polydispersity index kept narrow (PDI = 1.12-1.50), indicating a“living”/control polymerization process. Secondly, effects of the amount of the cross-linker on the properties of the cross-linked nanoparticles were studied. The results showed that the diameter of the obtained nanoparticles increased first and then decreased with the amount of the cross-linker in the range of 51-130 nm. Lastly, chiral separation of the nanoparticles for D,L-arabinose, (±)-3-amino-1,2-propanediol was investigated. It was found that the chiral nanoparticles not only had good chiral separation ability but also could be reused.
2. Three chiral P(VBPG)s with different molecular weights containing alkynyl end group were obtained using 2-bromo-isobutyrate-3-butyl acetylene (BEiB) as functional initiator via ATRP method. Then, the P(VBPG) chains were grafted onto the surfaces of silica nanoparticles with azide group via the "click" chemistry to prepare the chiral hybrid naoparticles. The ability of enantioselective recognition of the three organic/inorganic silica hybrid nanoparticles for tartaric acid and (±)-3-amino-1,2-propanediol was investigated. It was found that hybrid nanoparticles had good chiral separation ability. Finally, we investigated the chiral hybrid nanoparticles as the chiral stationary phases (CSPs) for high-performance liquid chromatography, it was found that the chiral hybrid nanoparticles in chromatography column as the fixity can reach the baseline separation of Mandelic Acid.
主要研究内容和结果如下:
(1)选用手性的VBPG为单体,二乙烯基苯(DVB)为交联剂,偶氮二异丁腈(AIBN)为引发剂,P(VBPG)(Mn,GPC = 6200 g/mol, Mw/Mn = 1.12)为Macro-RAFT试剂,甲苯为溶剂,正十六烷(HD)为助表面活性剂,十二烷基苯磺酸钠为乳化剂进行RAFT细乳液聚合。首先在无交联剂的情况下,研究了VBPG的RAFT细乳液聚合动力学,发现所得到的P(VBPG)分子量随转化率的提高而线性增长,且聚合物分散性指数较小(PDI = 1.12~1.50),符合“活性”/可控自由基聚合特征。在交联剂存在下,研究了交联剂用量对所得到的交联P(VBPG)纳米粒子性能的影响。结果表明:纳米粒子的粒径(51-130 nm)随交联剂用量的增加呈现先增大后减小的变化趋势。用阿拉伯糖和醇氨等外消旋化合物的手性拆分实验发现:该纳米粒子不但有较好的手性拆分能力,而且还可以重复使用。
(2)以功能性的2-溴异丁酸-3-炔丁酯(BEiB)为引发剂,采用ATRP法首先合成了三种含末端炔基不同链长的手性聚合链P(VBPG)。然后,使用“click”化学方法成功地将该聚合链接枝到含有叠氮的二氧化硅的表面,并考察了三种不同链长二氧化硅有机/无机杂化纳米粒子对酒石酸和醇胺等外消旋体手性拆分实验。发现该纳米粒子同样具有很好的手性拆分性能。最后考察了该手性杂化粒子在手性柱中作固定相进行HPLC手性拆分,实验发现该杂化粒子作为固定相能够对外削旋扁桃酸达到基线分离。
In this thesis, 6-O-p-vinylbenzyl-1,2:3,4-Di-O-isopropylidene-D-galactopyranose (VBPG) was selected as the monomer: (1) various cross-linked chiral nanoparticles were prepared by RAFT miniemulsion polymerization with different amounts of cross-linker, and (2) grafting chiral P(VBPG) chains to the silica surface by the combination ATRP and "click" chemistry method, to obtain chiral hybrid silica nanoparticles. And then studied the chiral separation and other related properties of the two kinds of nanoparticles.
The results were shown as follows:
1. VBPG was selected as the monomer, divinyl benzene (DVB) as the cross-linker if used, 2,2'-azobisisobutyronitrile (AIBN) as the initiator, P(VBPG) (Mn,GPC = 6200 g/mol, Mw/Mn = 1.12) as the Macro-RAFT agent, n-hexadecane (HD) as the co-emulsifier, toluene as the solvent, sodium dodecyl benzene sulfonate as the emulsifier for the RAFT miniemulsion polymerization. Firstly, the kinetics of RAFT miniemulsion polymerization was studied without cross-linker. The results showed P(VBPG) molecular weight increased with conversion and the polydispersity index kept narrow (PDI = 1.12-1.50), indicating a“living”/control polymerization process. Secondly, effects of the amount of the cross-linker on the properties of the cross-linked nanoparticles were studied. The results showed that the diameter of the obtained nanoparticles increased first and then decreased with the amount of the cross-linker in the range of 51-130 nm. Lastly, chiral separation of the nanoparticles for D,L-arabinose, (±)-3-amino-1,2-propanediol was investigated. It was found that the chiral nanoparticles not only had good chiral separation ability but also could be reused.
2. Three chiral P(VBPG)s with different molecular weights containing alkynyl end group were obtained using 2-bromo-isobutyrate-3-butyl acetylene (BEiB) as functional initiator via ATRP method. Then, the P(VBPG) chains were grafted onto the surfaces of silica nanoparticles with azide group via the "click" chemistry to prepare the chiral hybrid naoparticles. The ability of enantioselective recognition of the three organic/inorganic silica hybrid nanoparticles for tartaric acid and (±)-3-amino-1,2-propanediol was investigated. It was found that hybrid nanoparticles had good chiral separation ability. Finally, we investigated the chiral hybrid nanoparticles as the chiral stationary phases (CSPs) for high-performance liquid chromatography, it was found that the chiral hybrid nanoparticles in chromatography column as the fixity can reach the baseline separation of Mandelic Acid.
引文
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