本研究針對鄰苯二甲酸二(2-乙基己基)酯(di(2-ethylhexyl) phthalate, DEHP)製備具選擇性吸附材，並與光子晶體結合發展高靈敏度的DEHP光學感測器。研究中以甲基丙烯酸(methacrylic acid, MAA)以及苯乙烯(styrene, Sty)為功能性單體，乙二醇二甲基丙烯酸酯(ethylene glycol dimethacrylate, EGDMA)為交聯劑製備高分子，高分子吸附能力隨styrene含量增加而增加，卻隨MAA比例提高而降低，顯示高分子的疏水性及π-π作用力與EGDMA聚合後形成之微孔結構是吸附DEHP的主要關鍵，合成時使用乙腈(acetonitrile, ACN)與甲苯(toluene)體積比3:1的複合溶劑可使拓印高分子(molecularly imprinted polymer, MIP)中MAA及Sty均勻分布因而產生最高吸附量。以DEHP: MAA: styrene: EGDMA莫爾比為 1:8:5:10製備的吸附材可在20分鐘對DEHP達吸附平衡，其吸附行為符合擬二階吸附動力 (pseudo second order, PSO)，速率常數K2=0.62 g/mg*min，等溫吸附符合Freundlich模式，其吸附常數為KF=2.35，且飽和吸附量高達38.91 mg/g，並擁有良好的選擇性，其吸附DEHP之能力分別為其餘環境荷爾蒙雙酚A(Bisphenol A, BPA)、酚甲烷(phenol)、雌二醇(estradiol, E2)及鄰苯二甲酸二丁酯(dibutyl phthalate, DBP)的13.5、21.7、6.8及5.9倍。將高分子製備成反蛋白石光子晶體感測器(molecularly imprinted photonic crystal, MIPC)後，可由晶格膨脹產生的布拉格衍射波長紅移響應感測結果，以最佳親和力之比例DEHP: MAA: styrene: EGDMA= 1:8:5:10及合成溶劑ACN與toluene體積比3:1時，感測器在1.5 ppm下可位移26.6 nm，並且感測響應時間只需要1分鐘，經過10次循環重複利用仍保持感測穩定度，與MIP同樣對於BPA、phenol、E2、DBP有良好的選擇性，其偵測極限可至1.6 ppb，透過加入250 mM之氯化鈉(NaCl)，可使偵測極限下探至31 ppt；其感測性能並不受自來水基質之影響，在自來水感測當中偵測極限可至1.8 ppb，並透過250 mM NaCl的加入使偵測極限達到36 ppt。

In this study, a functional selective adsorbent and a corresponding inverse opal sensor for di(2-ethylhexyl) phthalate (DEHP) adsorption and detection have been prepared with a molecular imprinting technique. The molecularly imprinted polymer (MIP) was prepared with methacrylic acid (MAA) and styrene (Sty) as functional monomers and ethylene glycol dimethacrylate (EGDMA) as crosslinker. Adsorption ability of the MIP increased and decreased respectively with increasing content of styrene and MAA. Moreover, there was no significant adsorption difference between imprinted and non-imprinted polymers. Accordingly, the micromeshes formed between EGDMAs might be the active sites for DEHP adsorption and increased hydrophobicity/- interaction promoted the adsorption. Owing to different interaction with the mononers, synthesis with acetonitrile (ACN) and toluene co-solvents at a volume ratio of 3:1 resulted in the highest adsorption ability. The polymer prepared with the DEHP: MAA: Sty: EGDMA molar ratio of 1:8:5:10 quickly reached an adsorption equilibrium at 20 minutes. In addition, the adsorption followed the pseudo-second-order (PSO) kinetics with a rate constant (K2) of 0.62 g/mg*min and the Freundlich isotherm with a high adsorption constant (KF) of 2.35 and a high adsorption capacity of 38.91 mg/g. Besides, the polymer had great selectivity compared with other endocrine disrupting chemicals (EDCs) such as bisphenol A, estradiol and pheonl. The molecularly imprinted photonic crystal (MIPC) responded capture of DEHP in terms of red-shift of the Bragg diffraction as a result of lattice expansion. When it applied in the sensor, it red-shifted the diffraction by 26.6 nm at 1.5 mg/L DEHP. The sensor rapidly responsed in 1 minute, and it was stable after reusing 10 times, and it also has great selectivity with other EDCs. The limit of detection (LOD) is 1.6 ppb, with the help of salting effect the LOD even could reach 31 ppt. The sensor also had 1.8 ppb of LOD in tap water and with salting effect had 36 ppt, indicating that the it didn’t influence by the matrix of tap water. 

摘要 i
Abstract ii
致謝 iii
主目錄 iv
表目錄 vii
圖目錄 viii
一、前言 1
1.1 研究背景與動機 1
1.2 研究目的 4
二、文獻回顧 5
2.1 塑化劑的分析與感測 5
2.2 分子拓印材料 6
2.2.1 分子拓印原理 7
2.2.2 分子拓印組成 8
2.2.3 分子拓印材料應用 12
2.2.4 塑化劑分子拓印的近期研究 12
2.3 光子晶體(Photonic crystals, PCs) 15
2.2.1 光子晶體基本理論 15
2.2.2 蛋白石光子晶體製備 17
2.2.3 反蛋白石光子晶體製備 20
2.4 分子拓印光子晶體感測器(Molecularly Imprinted Photonic Crystal, MIPC) 22
2.4.1 蛋白石分子拓印光子晶體感測器 22
2.4.2 反蛋白石分子拓印光子晶體感測器 25
2.4.3 光子晶體感測器實際應用 28
2.4.4 拓印光子晶體於塑化劑的感測 31
三、研究方法 33
3.1 實驗材料 34
3.2 分子拓印材料 37
3.2.1 分子拓印聚合物製備 37
3.2.2 不同材料組成吸附實驗 37
3.2.3 膨脹率 38
3.2.4 等溫吸附 38
3.2.5 動力吸附 38
3.2.6　選擇性 39
3.3 光子晶體 39
3.3.1 SiO2膠體粒子合成 39
3.3.2 蛋白石光子晶體製備 40
3.3.3 分子拓印反蛋白石光子晶體製備 40
3.4 感測能力測試 41
3.4.1 MIPC不同組成感測性能 41
3.4.2　MIPC合成溶劑感測性能 41
3.4.3　響應時間 41
3.4.4　線性範圍與偵測極限 41
3.4.5　選擇性 42
3.4.6　重複利用性 43
3.4.7 鹽析效應 43
3.4.8　自來水中檢測 43
3.5 儀器分析 43
3.5.1 紫外光-可見光光譜儀 (UV-visible Spectrometer, UV-vis) 43
3.5.2 高效層析液相分析儀(High Performance Liquid Chromatography, HPLC) 44
3.5.3　傅立葉轉換紅外線光譜(Fourier Transform Infrared Spectrometer, FTIR) 44
3.5.4　掃描電子顯微鏡(Scanning Electron Microscopy, SEM) 44
四、結果與討論 46
4.1 分子拓印材料 46
4.1.1 功能性單體MAA 46
4.1.2 功能性單體Sty 48
4.1.3 複合功能性單體比例比較 49
4.1.4 合成溶劑比例 51
4.1.5　傅立葉轉換紅外光譜儀(FTIR) 53
4.1.6 動力吸附曲線 54
4.1.7　等溫吸附曲線 59
4.1.8　選擇性 64
4.2　分子拓印光子晶體 66
4.2.1　不同組成感測比較 66
4.2.2 掃描電子顯微鏡(SEM) 69
4.2.3感測濃度範圍與偵測極限 72
4.2.4 響應時間 74
4.2.5 選擇性 75
4.2.6重複使用 76
4.2.7　鹽析效應 77
4.2.8 於自來水中檢測 80
五、結論 84
參考文獻 86

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