臺灣博碩士論文加值系統

本研究主要分為二部分，第一部份乃利用芳杯分子為骨架，成功地在芳杯下緣修飾兩系列之&;#21537;唑官能基，其中以含有苯基之&;#21537;唑芳杯為合成基本架構，隨後並以含有苯基&;#33981;之&;#21537;唑芳杯76與77為主要篩選金屬離子之主體分子。我們同時合成了以丙基將剩餘羥基保護起來的控制化合物78與79，並進行紫外–可見光光譜、螢光放射光譜與氫核磁共振光譜的量測，以觀察&;#21537;唑芳杯76–79與16種金屬離子的辨識能力，發現在甲醇/氯仿 (v/v = 4:1) 溶劑體系下，&;#21537;唑芳杯77與79分別對Ag+與Hg2+有專一選擇性，且&;#21537;唑芳杯77對於Ag+具有螢光增強141%之效應，而&;#21537;唑芳杯79則對Hg2+有螢光淬熄51%之現象。另外，由Job plot與氫核磁共振滴定光譜的結果顯示，&;#21537;唑芳杯77與79分別對Ag+與Hg2+分別傾向於以1:1之化學計量比進行錯合在下緣&;#21537;唑官能基上，且由Hill plot與Stern-Volmer plot找出其錯合常數，分別為(1.12 ± 0.17) × 104 M-1、(1.33 ± 0.20) × 104 M-1。第二部分則是研究柱形杯芳烴之合成條件，藉由三氟化硼的催化下，將含有雙取代基之單體與多聚甲醛在濃度為0.1 M之條件下進行合環反應，成功且快速地合成出高產率之柱形杯芳烴38與83；另外，我們將兩種不同單體以4:1之混合比例，利用上述條件，成功地在柱形杯芳烴上選擇性地引入雙丙炔基95。

This study is divided into two parts. First, two series of lower-rim modified calix[4]arene with pyrazole substituents were synthesized. Using phenyl pyrazole calix[4]arenes as basic synthesis frameworks, we synthesized phenylanthryl pyrazole calix[4]arenes 76 and 77 and control compounds 78 and 79 as fluorogenic ions sensors. Based on the results from UV-Vis, fluorescence and 1H-NMR spectrometry, we found that pyrazole calix[4]arenes 77 and 79 recognized Ag+ and Hg2+ with excellent selectivity in MeOH/CHCl3 (v/v = 4:1), respectively. Compound 77 induced 141% enhancement of fluorescence intensity toward Ag+, and compound 79 showed 51% fluorescence quenching effect toward Hg2+.Furthermore, the complexation of compound 77 with Ag+ and 79 with Hg2+ both showed 1:1 host-guest stoichiometry based on by Job plot obtained from fluorescence and 1H-NMR titration spectra. We also found the binding constants of 77 with Ag+ was (1.12 ± 0.17) × 104 M-1 and 79 with Hg2+ was (1.33 ± 0.20) × 104 M-1.Second, the research was focused on the reaction condition to synthesize pillar[5]arenes. Pillar[5]arenes 38 and 83 were successfully and facile synthesized by cyclization reaction with high yield. These compounds were obtained via borontrifloride etherate catalyzed procedure with 1,4-dialkoxyphenyl monomer and paraformaldehyde under 0.1 M solution. Besides, a synthetic route to difunctional pillar[5]arene 95 was also developed by combining two different monomers with 4:1 ratio using the conditions stated above.

中文摘要 ........................................................... i
Abstract ......................................................... iii
謝誌 ............................................................... v
目錄 ............................................................. vii
圖目錄 ............................................................. x
式圖目錄 .......................................................... xv
表目錄 ......................................................... xviii
附圖目錄 ......................................................... xix
化合物對照表 ................................................... xxiii
第一章 緒論 ........................................................ 1
1.1 超分子化學 ..................................................... 1
1.2 芳杯 ........................................................... 2
1.2.1 芳杯之合成與構形 ............................................. 2
1.2.2 芳杯衍生化反應 ............................................... 3
1.3 化學感測器 ..................................................... 5
1.3.1 設計原理 ..................................................... 5
1.3.2 螢光感測分子之訊號傳遞機制 ................................... 6
1.4 雪梨酮簡介 ..................................................... 9
1.4.1 雪梨酮化合物之合成 .......................................... 11
1.4.2 雪梨酮之反應性 .............................................. 12
1.5 吡唑化合物之簡介 .............................................. 17
1.5.1 吡唑之製備方式 .............................................. 18
1.5.2 吡唑化合物之性質探討 ........................................ 21
1.5.3 吡唑化合物於感測器上之應用例子 .............................. 23
1.6 柱形杯芳烴之簡介 .............................................. 27
1.6.1 柱形杯芳烴之製備方式 ........................................ 29
1.6.2 柱形杯芳烴之結構特性 ........................................ 30
第二章 研究動機與目的 ............................................. 32
第三章 結果與討論 ................................................. 34
3.1 p-tert-Butylcalix[4]arene 之合成研究 .......................... 34
3.2 合成氮上含有取代基之雪梨酮化合物 .............................. 35
3.2.1 路徑一：合成氮上含有取代基之雪梨酮化合物 .................... 36
3.2.2 利用雪梨酮化合物進行1,3-偶極環加成反應 ...................... 41
3.3 路徑二：利用「3-甲基-1-氫-吡唑」形成含有吡唑官能基之化合物 .....57
3.3.1 合成含有苯基之吡唑化合物56 .................................. 57
3.3.2 合成含有苯基蒽之吡唑化合物57 ................................ 59
3.4 將氮上含有取代基之吡唑化合物與芳杯進行取代反應 ................ 61
3.4.1 合成下緣含有苯基吡唑取代之芳杯化合物 ........................ 61
3.4.2 合成下緣含有苯基蒽吡唑取代之芳杯化合物 ...................... 63
3.5 下緣含苯基蒽之吡唑芳杯化合物之金屬離子篩選研究 ................ 65
3.5.1 下緣含有單取代與雙取代之苯基蒽吡唑芳杯化合物76–79於甲醇/氯仿 (v/v = 4:1)之莫耳吸收係數 ......................................... 66
3.5.2 下緣含有單取代與雙取代之苯基蒽吡唑芳杯化合物76–79於甲醇/氯仿 (v/v = 4:1) 中對金屬離子篩選能力之研究 ............................ 68
3.5.3 下緣含有雙取代之苯基蒽吡唑芳杯化合物之詳細滴定研究 .......... 75
3.5.4 下緣含有雙取代之苯基蒽吡唑芳杯化合物77與79之氫核磁共振光譜詳
細滴定研究 ........................................................ 80
3.5.5 含苯基蒽取代之吡唑控制化合物之金屬離子篩選研究 .............. 94
3.6 柱形杯芳烴 (pillar[5]arene)之合成研究 ........................ 100
3.6.1 單一柱形杯芳烴 (monopillar[5]arene) 之合成研究 ............. 101
3.6.2 混摻柱形杯芳烴 (copillar[5]arene)之合成研究 ................ 106
第四章 結論 ...................................................... 110
第五章 實驗部分 .................................................. 112
第六章 參考文獻 .................................................. 154
第七章 附圖 ...................................................... 162
簡歷 ............................................................. 190

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