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分子拓印高分子(Molecularly Imprinted Polymer)有非共價與共價性MIP兩種製備方式，共價性MIP則是拓印分子和單體先經由共價作用形成化合物，再加入交聯劑進行交聯聚合反應製得；非共價性MIP主要為單體與模板分子形成錯合物，並加入交聯劑進行交聯聚合反應而形成。
本實驗首先製備(R)及(S)-BIONL作模板分子，以合成兩種形式的分子拓印聚合物，並經移除模版後形成分子拓印高分子(MIP)，為了分離掌性的萘酚(R-和S-)，以HPLC的方式，並用這些分子拓印聚合物為管柱固定相進行測試；結果顯示，官能基單體使用甲基丙烯酸(MAA)，交聯劑選用乙二醇二甲基丙烯酸酯(EGDMA)，溶劑以二氯甲烷的方式所製得分子拓印材質較適用HPLC管柱。

Molecularly Imprinted Polymer (MIP) can be made by using non-covalent and covalent bonding. Covalent MIP is prepared from polymerization of the compound which is made by using the mixture of functional monomer , template and crosslinker .Non-covalent MIP is mainly made from polymerization of functional monomer , template and crosslinker.
This experiment was to prepared (R)- and (S)-BIONL as templates to synthesize two kinds of MIP. These MIPs were tested by using HPLC method as column absorbents for separation of chiral BINOL (R- and S-). The results showed that MIPs made by MAA, EGDMA, and CH2Cl2 were suitable for absorbents of HPLC column

中文摘要…………………………………………………………………I
英文摘要………………………………………………………………...II
目錄……………………………………………………………………..III
圖目錄…………………………………………………………………..IV
第一章緒論………………………………………………………………1
1-1掌性化學……………………………………………………………..1
1-2 1,1，-二-2-萘酚（BINOL）的介紹………………………………….6
1-3分子拓印聚合物……………………………………………………10
1-3-1分子拓印原理……………………………………………….10
1-3-2 MIP 之發展歷史……………………………………………16
1-3-3發展契機…………………………………………………….17
1-3-4材質與作法介紹…………………………………………….19
1-4分子拓印聚合物之影響因素與條件選擇…………………………22
1-4-1選擇拓印分子(template)……………………………..…….22
1-4-2選擇官能基單體(functional monomer)……………………24
1-4-3選擇交聯劑(crosslinker)………………...…………………27
1-4-4選擇溶劑……………………………………………………29
1-5分子拓印聚合物的應用……………………………………………31
1-5-1分析化學上應用……………………………………………31
1-5-2食品工業之應用……………………………………………34
1-5-3藥物與生化物質之分子辨識(recognition)與鏡像選擇性應用…………………………………………………………..35
1-5-4分子拓印聚合物之特性……………………………………37
第二章 研究動機………………………………………………………39
第三章 實驗……………………………………………………………41
3-1 儀器………………………………………………………………...41
3-2 試藥及溶劑………………………………………………………...42
3-3 分析與分離方法…………………………………………………...43
3-4 實驗步驟…………………………………………………………...44
3-4-1合成目標分子(template)…………………………………...44
3-5非共價性聚合材質製備與鑑定……………………………………56
3-6共價性聚合材質製備與鑑定………………………………………65
第四章 結果與討論……………………………………………………69
4-1 合成模板分子……………………………………………………...69
4-1-1合成1,1，-二-2-萘酚（BINOL）(1,1，-bi-2-naphthol) (2)…69
4-1-2鹽類 N-benzylcinchonidium chloride(4)的合成………….69
4-1-3(R)- 1,1，-二-2-萘酚((R)- ( + ) -1,1，-bi-2-naphthol) (5)與(S)- 1,1，-二-2-萘酚((S)- (－) -1,1，-bi-2-naphthol) (6)的離析…………………………………………………….70
4-1-4甲基丙烯醯氯（2-Methyl-acryloyl chloride）(8)的合成…71
4-1-5(R)- ( + ) -1,1，-bi-2-naphthol bis(2-methylacrylate)（9）
與(S)- (－) -1,1，-bi-2-naphthol bis(2-methylacrylate)(11)的合成…………………………………………………………..72
4-1-6(R)- ( + ) -1,1，-bi-2-naphthol 2-methylacrylate（10）與(S)- (－) -1,1，-bi-2-naphthol 2-methylacrylate (12)的合成…….73
4-2共價與非共價性聚合材質製備…..………………………………...74
第五章 結論………………………………………………………..…104
第六章 參考文獻……………………………………………………..106
第七章 附錄…………………………………………………………..108

圖目錄
7-1核磁共振光譜
附圖1-1 (R)- 1,1，-二-2-萘酚(5)1H-NMR光譜圖…………………108
附圖1-2. (R)- 1,1，-二-2-萘酚(5)13C-NMR光譜圖…………………109
附圖2-1.(S)- 1,1，-二-2-萘酚(6)1H-NMR光譜圖…………………110
附圖2-2. (S)- 1,1，-二-2-萘酚(6) 13C-NMR光譜圖………………..111
附圖3-1. (R)- ( + ) -1,1，-bi-2-naphthol bis(2-methylacrylate)（9）1H-NMR光譜圖………………………….……………..…112
附圖3-2. (R)- ( + ) -1,1，-bi-2-naphthol bis(2-methylacrylate)（9）13C-NMR光譜圖…………………………………………113
附圖4-1. (R)- ( + ) -1,1，-bi-2-naphthol 2-methylacrylate（10）
1H-NMR光譜圖……………………………………………114
附圖4-2. (R)- ( + ) -1,1，-bi-2-naphthol 2-methylacrylate（10）
13C-NMR光譜圖…………………………………………….115
附圖5-1. (S)- (－) -1,1，-bi-2-naphthol bis(2-methylacrylate) (11) 1H-NMR光譜圖…………………………………………….116
附圖5-2. (S)- (－) -1,1，-bi-2-naphthol bis(2-methylacrylate) (11) 13C-NMR光譜圖……………………………………………117
附圖6-1. (S)- (－) -1,1，-bi-2-naphthol 2-methylacrylate (12)
1H-NMR光譜圖………………………………………….118
附圖6-2. (S)- (－) -1,1，-bi-2-naphthol 2-methylacrylate (12) 13C-NMR光譜圖……………………………………………………119
7-2 質譜圖
附圖7. (R)- 1,1，-二-2-萘酚(5)質譜圖…………………………...120
附圖8. (S)- 1,1，-二-2-萘酚(6)質譜圖……………………………120
附圖9. (R)- ( + ) -1,1，-bi-2-naphthol bis(2-methylacrylate)（9）質譜圖……………………………………………………………..121
附圖10. (R)- ( + ) -1,1，-bi-2-naphthol 2-methylacrylate（10）質譜圖
………………………………………………………………..121
附圖11. (S)- (－) -1,1，-bi-2-naphthol bis(2-methylacrylate) (11)質譜圖
………………………………………………………………...122
附圖12. (S)- (－) -1,1，-bi-2-naphthol 2-methylacrylate(12)質譜圖122
7-3紫外線吸收光譜
附圖13. (R)- 1,1，-二-2-萘酚(5) 紫外線吸收光譜………………..123
附圖14. (S)- 1,1，-二-2-萘酚(6) 紫外線吸收光譜………………...123
附圖15. (R)- ( + ) -1,1，-bi-2-naphthol bis(2-methylacrylate)（9）紫外線吸收光譜…………………………………………………124
附圖16. (R)- ( + ) -1,1，-bi-2-naphthol 2-methylacrylate（10）紫外線吸收光譜……………………………………………………124
附圖17. (S)- (－) -1,1，-bi-2-naphthol bis(2-methylacrylate) (11) 紫外
線吸收光譜…………………………………………………125
附圖18. (S)- (－) -1,1，-bi-2-naphthol 2-methylacrylate (12) 紫外線吸收光譜………………………………………………………125
7-4紅外線吸收光譜
附圖19. (R)- 1,1，-二-2-萘酚(5) 紅外線吸收光譜……………….126
附圖20. (S)- 1,1，-二-2-萘酚(6) 紅外線吸收光譜……………….126
附圖21. (R)- ( + ) -1,1，-bi-2-naphthol bis(2-methylacrylate)（9）紅外線吸收光譜………………………………………………....127
附圖22. (R)- ( + ) -1,1，-bi-2-naphthol 2-methylacrylate（10）紅外線吸收光譜……………………………………………….….127
附圖23. (S)- (－) -1,1，-bi-2-naphthol bis(2-methylacrylate) (11) 紅外線吸收光譜…………………………………………………128
附圖24. (S)- (－) -1,1，-bi-2-naphthol 2-methylacrylate(12) 紅外線吸收光譜………………………………………………………128

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