本研究利用有機物聚合法及溶膠-凝膠法製備以雙酚A為模板的有機無機複合拓印高分子，藉由無機物的剛性結構提高對模板分子的拓印程度，並以有機物的膨潤性增進標的物於高分子內的傳輸效能，以達到高吸附量與辨識能力的目的。研究顯示當交聯劑四乙氧基矽烷(Tetraethyl orthosilicate)與3-(甲基丙烯醯氧)丙基三甲氧基矽烷(3-(Methacryloyloxy)propyl trimethoxysilane) 莫耳比例為15：10時拓印高分子有最佳質地及吸附量。TGA分析指出材料中有機物與無機物間的重量比例為1：1，模板分子萃取率近100%。等溫吸附數據及Langmuir模式模擬結果得出拓印高分子最大吸附量可高達65.8 mg/g。由29Si及13C NMR圖譜分析可知雙酚A模板於合成過程中以Si-O-C共價鍵結方式拓印於高分子內，完整的孔洞結構大幅提升高分子對雙酚A的吸附量，使拓印因子(α)有2.5優異表現，此外拓印高分子對結構類似物質Phenol、Bis(2-hydroxyphenyl)methane、4-tert-butylphenol及17β- Estradiol的選擇性因子(β)為78.2、11.5、2.3和趨近於無限大，在HPLC層析實驗中對phenol及4-tert-butylphenol得到分離因子為31.8及3.9，重複實驗證實拓印高分子的無機孔洞擁有良好的穩定性，在5次的吸附及萃取循環中相對標準偏差為3.9%。整體結果顯示有機無機複合拓印高分子對雙酚A具高吸附量與選擇性，可作為分離、層析或感測元件的先進材料。

Abstract
In this study, a BPA-imprinted organic-inorganic hybrid, which exhibits high adsorption and recognition capability, was successfully fabricated by using polymerization and sol-gel processes. Rigidity of inorganic framework improves imprinting extend. In addition, flexible organic moiety allows high mass transfer in the imprinted polymer. Tetraethyl orthosilicate (TEOS) and 3-(methacryloyloxy)propyl trimethoxysilane (MEMO) were used as the inorganic and organic cross linkers, respectively, and an optimal TEOS-to-MEMO molar ratio for the highest adsorption capacity was 15:10. TGA analysis indicates that the imprinted polymer contains equal mass in the organic and inorganic components. Almost 100% imprinted molecules were extracted from the imprinted matrix to leave a high quantity of available sites (1.881020 /g) for rebinding the target. The maximum binding capacity, which was calculated from Langmuir model, was 65.8 mg/g. The 29Si and 13C NMR spectra reveal that the BPA molecules were imprinted into the cavities in terms of formation of Si-O-C covalent bonding. A high level of imprinting led to a imprinting factor (α) of 2.5, and resulted in the selectivity factor (β) of 78.2, 11.5, 2.3 and infinity for Phenol, Bis(2-hydroxyphenyl)methane (2HDPM), 4-tert-butylphenol (4TBP) and 17β- Estradiol (E2) analogues, respectively. Moreover, the separation factor (s) for phenol and 4TBP was 31.8 and 3.9, respectively, in the HPLC column test. Recoverability of the hybrid shows a small relative standard deviation of 3.9% reveling a high stability of imprinted cavities. These results in this study clearly indicate that the hybrid exhibits outstanding adsorption and recognition performance, which is highly promising for the applications in separation, chromatography and sensing.

目 錄
摘要 I
Abstract II
誌謝 IV
目錄 V
表目錄 VIII
圖目錄 IX
第一章、前言 1
1.1 研究動機 1
1.2 研究目的 2
第二章、文獻回顧 3
2.1 雙酚A 3
2.2 分子拓印技術概念與發展 5
2.3 分子拓印方式 6
2.3.1 共價鍵結 7
2.3.2 非共價鍵結 8
2.3.3 共價鍵與非共價鍵結特性比較 9
2.4 分子拓印材料 11
2.4.1 有機分子拓印 11
2.4.2 無機分子拓印 12
2.4.3 有機無機複合分子拓印 13
2.4.4 分子拓印材料的特性與鑑定 16

2.5 分子拓印材料應用 18
2.5.1 分離與層析 18
2.5.2 感測器 19
2.5.3 藥物傳輸 20
2.5.4 觸媒 21
第三章、研究方法 22
3.1 實驗材料 24
3.2 分子拓印高分子合成方法 25
3.3 儀器分析 27
3.3.1 傅立葉轉換紅外線光譜儀 (Fourier transform infrared spectrometer, FTIR) 27
3.3.2 熱重分析儀 (Thermal gravimetric analysis, TGA) 27
3.3.3 等溫氮氣吸脫附分析 (Nitrogen adsorption-desorption isotherm Measurement) 30
3.3.4 紫外光-可見光光譜儀 (UV-visible spectrophotometer, UV-Vis) 30
3.3.5 固態核磁共振光譜儀 (Solid-State Nuclear magnetic resonance NMR Spectroscopy, NMR) 30
3.3.6高效能液相層析儀 (High performance liquid chromatography, HPLC) 31
3.4 吸附特性 32
3.4.1 吸附能力測試 32
3.4.2 拓印因子評估 33
3.4.3 Scatchard分析 33
3.4.4 拓印選擇性測試 34
第四章、結果與討論 35
4.1 分子拓印高分子製備 35
4.2 交聯劑組成最佳化 36
4.3 高分子特性鑑定 40
4.4 拓印高分子組成及孔洞分析 42
4.4.1 拓印高分子組成分析 42
4.4.2 拓印高分子模板移除效率及有效孔洞數量 44
4.4.3 拓印高分子孔洞結構探討 46
4.5 分子拓印高分子吸附特性 50
4.5.1 拓印與未拓印高分子吸附 50
4.5.2 等溫吸附 (Binding isotherm) 51
4.5.3 Scatchard分析 53
4.5.4 選擇性吸附 55
4.5.5 HPLC分析 58
4.5.6 重複吸附實驗 60
第五章、結論 61
參考文獻 62

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