直至今日殘留農藥檢測愈漸受到重視，而表面增顯拉曼散射（SERS）及分子印跡技術（MIP）提供了在不同環境下檢測微量殘留分子。本研究藉由將賽滅寧之表面印跡層（MIP）合成在金奈米粒子表面，由MIP去增加對待測物的選擇性並且透過塑料特性提高對環境的穩定性，製造方法在液相合成中製備，具有簡易、低成本之優勢。掃描式電子顯微鏡（SEM）及穿透式電子顯微鏡（TEM）顯示MIP-SERS粒徑大小為16±1 nm，且外層MIP層厚度為1 nm。由於外層MIP層之閘極效應提升拉曼效應，使MIP-SERS系統表現出優於單獨金球體之拉曼散射增顯效應。本研究對選用不同摩爾數量之MIP-SERS基板進行SERS增顯提升效果進行詳細的比較，在實驗結果中進行分析及解釋，並且使用賽滅寧（CYP）作為探測分子驗證SERS效應，證明本研究之MIP-SERS活性基板適用於拉曼散射增顯檢測，藉由已知的雷射區域、焦距、濃度和莫耳重量等數據帶入後得到NBulk，此外對於NSERS做兩個基本假設：其一，MIP-SERS 粒子緊密排列且僅一層無重複堆積；其二，原先所有已印跡並移除之 CYP 位置皆已被填入，由MIP-SERS_90樣品取四個區域，平均計算得到EF值為2.88×106。同時比較相似合成除蟲菊精類結構之農藥—百滅寧，它們相似的結構可以使印跡賽滅寧位置之MIP-SERS基板在除蟲菊精類農藥檢測上同樣具有高強度拉曼峰值，並且將它實際應用到混合農藥及茶葉檢驗上，證明本研究之SERS活性基板為一具有前瞻性之微量除蟲菊精類檢測工具。

Pesticide residues detection draws more and more attention, by combining Surface-enhanced Raman Scattering (SERS) and Molecularly Imprinted Technique (MIT) which could provide trace molecule detection. In this study, the surface imprinted layer (MIP) of Cypermethrin was synthesized on the surface of the gold nanoparticles, and the MIP was used to increase the hot spots of the analyte. Medium preparation has the advantages of simplicity and low cost. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) showed that the MIP-SERS particle size was 16±1 nm and the outer MIP layer thickness was 1 nm. Since the gate effect of the outer MIP layer enhances the Raman effect, the MIP-SERS system exhibits a Raman scattering enhancement effect superior to that of the individual gold spheres. In this study, a detailed comparison of SERS enhancement effects using different molar amounts of MIP-SERS substrates was carried out, and analysis and interpretation were carried out in the experimental results, and the SERS effect was verified by using CYP as a probe molecule. The MIP-SERS active substrate is suitable for Raman scattering enhancement detection, an estimated value of the enhancement factor (EF) of the MIP-SERS
substrate was calculated through the following equation:
EF = (ISERS/ NSERS)/ (IRS/NRS)
Both ISERS and IRS are intensities obtained from SERS and normal Raman conditions, respectively. NSERS and NRS represent the number of adsorbed target molecules; N can be determined by considering the target molecule size with respect to the geometries of both SERS and non-SERS substrates. For NRS, it is assumed that the target molecules arrange in a single layer on a flat surface while for NSERS, the surface area created by the MIP-SERS was calculated first before determining the number of target molecules that could be adsorbed onto the said surface. With this, two main assumptions were made: 1. MIP-SERS were arranged on a single layer, and 2. the Raman laser spot having a diameter of 1 µm could cover an estimate of 2890 MIP-SERSand the EF value is 2.88×106. The pesticides which similar to the pyrethroid structure were compared. The similar structure can make the MIP-SERS substrate with the high-intensity Raman peak in the detection of pyrethroid pesticides. And it was applied to the mixed pesticide and tea inspection, which proved that the SERS active substrate of this study is a forward-looking detection tool.

摘要................................I
SUMMARY................................II
誌謝................................XII
目錄................................XIV
表目錄................................XVII
圖目錄................................XVIII
第一章 緒論................................1
1.1 前言................................1
1.2 研究動機................................3
1.3 研究目的................................4
第二章 文獻回顧與理論基礎................................5
2.1 拉曼活性基板之製作................................5
2.1.1 減去法（Top-down techniques）................................5
2.1.2 加成法（Bottom-up techniques）................................5
2.1.3 複合型（Combination techniques）................................6
2.1.4 模板輔助型（Template-assisted fabrication）................................6
2.1.5 內核—外殼形式（Core-shell）................................6
2.2 拉曼理論................................7
2.2.1 拉曼光譜機制................................7
2.2.2 表面拉曼增顯效應 (SERS)................................8
2.2.3 表面電漿（Surface plasmon）................................13
2.3 分子印跡技術 (Molecular imprinting technology, MIT)................................13
2.3.1 多功能單體................................14
2.3.2 交聯劑................................14
2.3.3 引發劑................................15
2.3.4 溶劑（致孔劑）................................15
2.3.5 索式提取裝置（Soxhlet extraction）................................15
2.3.6 MIP合成機制................................16
2.4 MIP-SERS 合成機制及其製備................................18
2.4.1 奈米粒子合成技術................................18
2.4.2 表面修飾技術................................19
2.4.3 MIP 效應................................20
2.4.4 SERS和MIP 疊加效應................................21
2.5 擬除蟲菊酯（Pyrethroid）................................22
2.6 文獻與理論基礎之小節................................22
第三章 材料與方法................................23
3.1 MIP-SERS活性基板製備步驟................................23
3.1.1 合成奈米金粒子................................24
3.1.2 以矽氧烷偶聯劑（3-(巰丙基)三甲氧基矽烷, MPS）修飾金粒子表面................................24
3.1.3 表面印跡聚合物................................24
3.2 材料方法與理論機制................................24
3.3 拉曼檢測................................25
3.3.1 矽基板清洗................................25
3.3.2 農藥標準溶液製備................................26
3.3.3 茶葉樣品模擬農藥汙染製備................................26
3.3.4 拉曼光譜分析量測方式（定量乾式量測）................................26
3.3.5 拉曼光譜校正................................26
3.3.6 訊號處理................................27
3.3.7 增顯因子（Enhancement Factor, EF）之評估................................27
3.4 分析儀器................................28
3.4.1 掃描式電子顯微鏡 (SEM)................................28
3.4.2 原子力顯微鏡 (AFM)................................29
3.4.3 功能性穿透式電子顯微鏡 (cryo-TEM)................................30
3.4.4 拉曼光譜儀................................30
3.4.5 可見光紫外光分光光譜儀................................31
3.4.6 材料與方法之小節................................31
第四章 MIP-SERS 活性基板結構及形貌之特性分析................................32
4.1 合成奈米金粒子................................32
4.2 以MPS修飾奈米粒子表面................................35
4.3 分子印跡聚合物 (MIP)................................40
4.4 不同印跡分子數量之基板................................42
4.5 基板應用於分子探針研究之結論................................45
第五章MIP-SERS活性基板應用於苯氧基農藥檢測之研究................................46
5.1 雷射波長對於農藥之選擇性................................46
5.2 MIP-SERS活性基板於模板分子（賽滅寧）之檢測極限分析................................49
5.3 拉曼增顯因子之計算................................49
5.4 SERS活性基板於百滅寧之檢測極限定量分析................................51
5.5 與不同拉曼活性基板之討論................................52
5.5.1 分子印跡（MIP）與無分子印跡化合物（NIP）增顯效應................................52
5.5.2 MIP-SERS與單純金奈米粒子之活性基板討論................................53
5.6 SERS活性基板模擬實際情況之檢測極限定量分析................................54
5.6.1 SERS活性基板於混合農藥之檢測極限定量分析................................54
5.6.2 SERS活性基板於模擬茶葉汙染實體之檢測................................55
5.7 與現有研究進行討論................................55
5.8 較厚印跡層................................57
5.9 基板應用於農藥殘留檢測之結論................................58
結論................................59
未來展望................................60
參考文獻................................61
附錄A 振動光譜................................72

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