請用此 Handle URI 來引用此文件：
http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/80264完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 鄭如忠(Ru-Jong Jeng) | - |
| dc.contributor.author | Shih-Hao Wang | en |
| dc.contributor.author | 王士豪 | zh_TW |
| dc.date.accessioned | 2022-11-24T03:03:29Z | - |
| dc.date.available | 2022-02-21 | - |
| dc.date.available | 2022-11-24T03:03:29Z | - |
| dc.date.copyright | 2022-02-21 | - |
| dc.date.issued | 2022 | - |
| dc.date.submitted | 2022-01-21 | - |
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Stefan, G.; Antony, J.; Ehrlich, S.; Krieg, H.; A Consistent and Accurate ab Initio Parametrization of Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu. The Journal of Chemical Physics 2010, 132, 154104. 115. Tersa, F. B.; Cao, X.; Dukor, R. K.; Nafie, L. A., Absolute Configuration Determination of Chiral Molecules in the Solution State Using Vibrational Circular Dichroism. Chirality 2003, 15, 743-758. 116. Takeshi, Y.; Tew, D. P.; Handy, N. C., A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP), Chemical Physics Letters 2004, 393, 51-57. 117. So, H.; Head-Gordon, M. Time-Dependent Density Functional Theory within the Tamm-Dancoff Approximation. Chemical Physics Letters 1999, 314, 291-299. 118. Barman, S.; Singh, A.; Rahimi, F. A.; Maji, T. K. Metal-Free Catalysis: A Redox-Active Donor–Acceptor Conjugated Microporous Polymer for Selective Visible-Light-Driven CO2 Reduction to CH4. J. Am. Chem. Soc. 2021, 143, 16284-16292. | - |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/80264 | - |
| dc.description.abstract | "本論文主要設計及合成一系列富勒烯衍生物、共軛小分子和高分子，作為光驅動二氧化碳還原反應之催化劑，並探討分子結構於材料性質、催化活性和催化穩定性之影響。 第一部分，首先以普拉托反應將4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazol le (DTBT)化學接枝至富勒烯吡咯烷上，形成二元體 (dyad)分子，簡稱為DTBT-C60，促使其吸收光譜紅位移，並探討其光學性質和光電化學性質的變化。紫外光-可見光光譜顯示長波長之吸收峰確實因DTBT分子的存在，而增加了400-520 nm區間的吸收範圍，吸收光譜的改善有助於DTBT-C60更好的利用太陽光產生更多的激子，PL以及TRPL的量測結果顯示，引入DTBT能更有效地拆解激子以及減少電荷再結合的機率，DTBT-C60的光電化學性質則分別利用光電壓衰退 (photovoltage decaying measurement)、電化學阻抗分析 (electrochemical impedance spectroscopy)以及光電流響應 (photocurrent response)實驗進行分析。DTBT-C60催化之反應系統在AM1.5G的光譜之太陽模擬光源照射反應24小時後，產出一氧化碳為唯一產物，其產率為144 μmol·gcat-1。同位素的實驗證實水可以有效地作為電子的來源與DTBT-C60反應，且不需要任何犧牲劑添加，更重要地，DTBT-C60維持了非常持久的催化活性，可超越一個禮拜之久。 第二部分，使用萘雙亞醯胺作為電子授體單元，分別與thiophene、thienothiophene、bithiophene 和terthiophene，進行Stille coupling反應，合成一系列的有機共軛小分子，分別簡稱為NDI-2T、NDI-TT、NDI-4T和NDI-6T，並探討其結構上電子供體的能力對於它們的光電性質之影響，其中，由於導入較強推電子能力之電子供體，NDI-6T擁有最紅位移的吸收光譜、最長的激子壽命以及較佳的電子電洞拆解能力，將NDI-4T作為有機催化劑應用於光催化二氧化碳還原反應，可產出168 μmol·gcat-1的一氧化碳產率，相較NDI-TT (111.9 μmol·gcat-1)、 NDI-2T (88.4 μmol·gcat-1)和NDI-6T (40.5 μmol·gcat-1)高出許多，除了NDI-6T外，其一氧化碳產率的趨勢隨著噻吩數量的增加而有所提升。然而，電子供體的推電子能力提升，能有效的縮短能隙，卻同時上移氧化能階，NDI-6T的氧化能階與水的氧化能階相同，降低NDI-6T陽離子氧化水以還原成中性態的驅動力，相對地，NDI-4T具有適當的氧化及還原電位、較低的電荷轉移電阻以及優異的光電流強度，因此，表現出最高的催化活性，而且，反應過程僅需使用水作為電子供體，不需要共催化劑及犧牲劑的加入，此部分之研究不只能展示有機共軛小分子作為催化劑之潛力，也探討了共軛小分子電子供體能力對於二氧化碳還原效率之影響。 第三部分，在共軛高分子的主鏈導入電子授體之萘雙亞醯胺單體，並分別與弱的推電子單元之biphenyl單體或拉電子單元之DTBT單體，利用Stille反應進行聚合形成兩個共軛高分子 (PNDI-BP和PNDI-DTBT)，合成之單體及共軛高分子均有使用核磁共振光譜儀進行結構鑑定，並以凝膠滲透層析測得分子量，並與市售之共軛高分子PNDI-2T針對它們的光學、電化學及結晶性質進行比較，紫外光可見光光譜顯示PNDI-DTBT擁有最寬廣的吸收光譜以及較強的吸收係數，吸收光譜的改善能使PNDI-DTBT更好的利用太陽光產出更多激子，XRD的分析顯示PNDI-2T表現出最好的結晶度，且具有明顯的π-π stacking的訊號。三個高分子催化劑進行二氧化碳光催化還原反應都能在少量水作為電子供體下產出一氧化碳，更重要的是PNDI-BP不只擁有了最高的一氧化碳產率90.0 μmol·gcat-1，也能夠產出甲烷作為產物，產率為1.7 μmol·gcat-1。TRPL及開環電壓衰退之分析，發現萘雙亞醯胺與非共平面的雙苯環單體共聚合之PNDI-BP，可有效地延長電子存活的時間及抑制電荷載子的再結合，電化學阻抗分析以及光電流響應實驗指出PNDI-BP具有最低的電荷傳遞電阻以及較佳的光電流強度，因此，可大幅的提升催化活性以及增加還原反應的產物量，PNDI-BP展現了非常好的可回收性以及卓越的長時間催化穩定性，可穩定產出產物至兩周之久。 綜合以上實驗，我們對於富勒烯衍生物、萘雙亞醯胺之小分子及高分子的結構設計有更進一步的認識與了解，這將有助於未來設計高催化效率及高穩定性的有機催化劑。" | zh_TW |
| dc.description.provenance | Made available in DSpace on 2022-11-24T03:03:29Z (GMT). No. of bitstreams: 1
U0001-1901202215290000.pdf: 16692818 bytes, checksum: 6cf55d6ff3b314f579e6ad4adeb5c5f8 (MD5) Previous issue date: 2022 | en |
| dc.description.tableofcontents | "目錄 誌謝 ii 摘要 vii Abstract v 目錄 xi 圖目錄 xi 表目錄 xxii 第一章 緒論 1 1-1 前言 1 1-2 二氧化碳還原的分類及基礎原理 3 1-2-1二氧化碳還原之分類 3 1-2-2光催化二氧化碳還原之反應機制 4 1-2-3光催化二氧化碳還原之可能反應途徑 7 1-2-4光催化二氧化碳還原之反應系統 9 1-2-5共催化劑及犧牲劑之應用 10 1-3 光催化劑 12 1-3-1無機材料作為光催化劑 12 1-3-1-1鈣鈦礦材料作為光催化劑 17 1-3-1-2金屬有機框架材料作為光催化劑 19 1-3-1-3 石墨衍生物材料作為光催化劑 21 1-3-2 有機材料作為光催化劑 24 1-3-2-1 有機孔洞高分子材料作為光催化劑 25 1-3-2-2 共軛有機框架材料作為光催化劑 26 1-4 研究動機 27 1-4-1 材料合成路徑 28 第二章 實驗 30 2-1 實驗所需化學試劑列表 30 2-2 實驗設備及儀器 32 2-3 材料合成 36 2-3-1 碳六十衍生物之合成 36 2-3-2 萘雙亞醯胺之有機共軛小分子及高分子之合成 45 2-4 氣相層析儀之定性與定量分析 57 2-5 光催化二氧化碳還原實驗方法 58 2-5-1 光催化二氧化碳還原實驗樣品製備 58 2-5-2 光催化二氧化碳還原實驗架設 58 2-5-3 光催化二氧化碳還原之產率計算 59 2-5-3-1 化學產率 59 2-5-3-2 量子產率 60 2-5-3-3 反轉換率及反轉頻率 61 第三章 結果與討論 62 3-1 碳六十發色團二元體作為有機催化劑於二氧化碳光催化還原之應用 62 3-1-1碳六十發色團二元體之研究動機 62 3-1-2碳六十發色團二元體之合成 64 3-1-2-1合成反應 64 3-1-2-2碳六十衍生物合成討論 66 3-1-3碳六十衍生物之結構鑑定 68 3-1-3-1 1H NMR結構鑑定 68 3-1-3-2 MALDI-TOF結構鑑定 71 3-1-4碳六十衍生物之光學性質分析 72 3-1-5碳六十衍生物之能階分析 73 3-1-6碳六十衍生物作為催化劑於光驅動二氧化碳還原之效率探討 76 3-1-7碳六十衍生物之二氧化碳吸附探討 79 3-1-8碳六十衍生物之光電化學性質探討 80 3-1-8-1光致發光光譜儀以及時間解析光致發光光譜儀 (PL, TRPL) 80 3-1-8-2光電壓衰退量測 (Photovoltage decaying measurement) 82 3-1-8-3電化學阻抗分析 (Electrochemical impedance spectroscopy) 85 3-1-8-4瞬態光電流響應 (Transient photocurrent responses) 87 3-1-9光催化二氧化碳還原反應之機制探討及同位素之實驗 88 3-1-10分子理論模擬 91 3-1-11碳六十衍生物於光驅動二氧化碳還原之長效催化活性分析 94 3-1-12結論 96 3-2 奈雙亞醯胺有機共軛小分子作為有機催化劑應用於光催化二氧化碳還原反應 97 3-2-1奈雙亞醯胺共軛小分子之研究動機 97 3-2-2有機共軛小分子之合成 97 3-2-2-1合成反應 98 3-2-2-2有機共軛小分子合成討論 98 3-2-3有機共軛小分子之1H NMR結構鑑定 100 3-2-4有機共軛小分子之光學性質分析 104 3-2-5有機共軛小分子之能階分析 106 3-2-6有機共軛小分子之X光繞射圖譜分析 108 3-2-7有機共軛小分子之時間解析光致發光光譜儀 109 3-2-8分子模擬 110 3-2-9有機共軛小分子作為催化劑於光驅動二氧化碳還原之效率探討 112 3-2-10有機共軛小分子之二氧化碳吸附之探討 114 3-2-11有機共軛小分子之光電性質分析 114 3-2-11-1光電壓衰退量測 (Photovoltage decaying measurement) 114 3-2-11-2電化學阻抗分析 (Electrochemical impedance spectroscopy) 115 3-2-11-3瞬態光電流響應 (Transient photocurrent responses) 116 3-2-12光催化二氧化碳還原反應同位素之實驗 116 3-2-13 NDI-4T之長效催化活性分析 118 3-2-14結論 120 3-3 奈雙亞醯胺共軛高分子作為有機催化劑應用於光催化二氧化碳還原反應 121 3-3-1萘雙亞醯胺共軛高分子之研究動機 121 3-3-2萘雙亞醯胺共軛高分子之合成 122 3-3-2-1高分子合成討論 122 3-3-3單體與高分子的結構鑑定 124 3-3-3-1單體結構鑑定 124 3-3-3-2高分子結構鑑定 126 3-3-4 共軛高分子的分子量性質 127 3-3-5 共軛高分子之光學性質分析 128 3-3-5-1共軛高分子溶液態吸收光譜分析 128 3-3-5-2共軛高分子薄膜態吸收光譜分析 130 3-3-6 共軛高分子能階分析 131 3-3-7 共軛高分子X光繞射圖譜分析 134 3-3-8 分子理論模擬 135 3-3-8-1幾何優化與構型 135 3-3-8-2基態與激發態電子雲分布 139 3-3-9 共軛高分子之二氧化碳吸附探討 141 3-3-10 共軛高分子作為催化劑於光驅動二氧化碳還原之效率探討 142 3-3-11 共軛高分子之光電化學性質探討 144 3-3-11-1光致發光光譜儀以及時間解析光致發光光譜儀 (PL, TRPL) 144 3-3-11-2光電壓衰退量測 (Photovoltage decaying measurement) 147 3-3-11-3電化學阻抗分析 (Electrochemical impedance spectroscopy) 148 3-3-11-4瞬態光電流響應 (Transient photocurrent responses) 149 3-3-12光催化二氧化碳還原反應同位素之實驗 150 3-3-13共軛高分子於光驅動二氧化碳還原之長效催化活性分析 152 3-3-14結論 157 第四章 總結及未來展望 158 第五章 參考文獻 161 附錄 170 相關研究成果 197 " | - |
| dc.language.iso | zh-TW | - |
| dc.subject | 共軛高分子 | zh_TW |
| dc.subject | 光催化劑 | zh_TW |
| dc.subject | 光反應 | zh_TW |
| dc.subject | 二氧化碳還原 | zh_TW |
| dc.subject | 富勒烯衍生物 | zh_TW |
| dc.subject | 有機共軛小分子 | zh_TW |
| dc.subject | photoreaction | en |
| dc.subject | CO2 reduction | en |
| dc.subject | fullerene derivatives | en |
| dc.subject | fulleropyrrolidine | en |
| dc.subject | conjugated small molecules | en |
| dc.subject | conjugated polymers | en |
| dc.subject | photo-catalysts | en |
| dc.title | 光驅動二氧化碳還原反應之有機催化劑研發 | zh_TW |
| dc.title | Development of Organocatalysts for Light-driven CO2 Reduction Reaction | en |
| dc.date.schoolyear | 110-1 | - |
| dc.description.degree | 博士 | - |
| dc.contributor.author-orcid | 0000-0002-6083-5822 | - |
| dc.contributor.advisor-orcid | 鄭如忠(0000-0002-0913-4975) | - |
| dc.contributor.coadvisor | 王立義(Leeyih Wang) | - |
| dc.contributor.coadvisor-orcid | 王立義(0000-0002-6368-0141) | - |
| dc.contributor.oralexamcommittee | 黃慶怡(Ying-Chun Tsai),賴育英(TUNG-LIANG LIAO),陳志堅(Leonard Chan Kwok Kou),鍾博文(SHOU-CHENG TSENG),(Shou-jen Tseng),(Shou-jen Tseng),(Shou-jen Tseng) | - |
| dc.subject.keyword | 二氧化碳還原,富勒烯衍生物,有機共軛小分子,共軛高分子,光催化劑,光反應, | zh_TW |
| dc.subject.keyword | CO2 reduction,fullerene derivatives,fulleropyrrolidine,conjugated small molecules,conjugated polymers,photo-catalysts,photoreaction, | en |
| dc.relation.page | 199 | - |
| dc.identifier.doi | 10.6342/NTU202200103 | - |
| dc.rights.note | 同意授權(限校園內公開) | - |
| dc.date.accepted | 2022-01-21 | - |
| dc.contributor.author-college | 工學院 | zh_TW |
| dc.contributor.author-dept | 高分子科學與工程學研究所 | zh_TW |
| 顯示於系所單位： | 高分子科學與工程學研究所 | |
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