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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 邱勝賢 | |
| dc.contributor.author | Tsung-Hsien Ho | en |
| dc.contributor.author | 何宗憲 | zh_TW |
| dc.date.accessioned | 2021-06-17T04:46:27Z | - |
| dc.date.available | 2023-08-24 | |
| dc.date.copyright | 2018-08-24 | |
| dc.date.issued | 2018 | |
| dc.date.submitted | 2018-08-01 | |
| dc.identifier.citation | 1. a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH, 1995; b) Lehn, J.-M. Science 1993, 260, 1762–1763.
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Lin, Y.-H.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Angew. Chem. 2013, 125, 10421–10426; Angew. Chem. Int. Ed. 2013, 52, 10231–10236. 21. a) Strauss, S. H. Chem. Rev. 1993, 93, 927–942; b) Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092–2095; c) Chen, N.-C.; Chuang, C.-J.; Wang, L.-Y.; Lai, C.-C.; Chiu, S.-H. Chem. Eur. J. 2012, 18, 1896–1900; d) Wang, L.-Y.; Ko, J.-L.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Chem. Eur. J. 2013, 19, 8850–8860. 22. Imine formation has been applied to construct rotaxanes by “clipping” macrocycles onto dibenzylammonium or pyridinium ion-containing dumbbell-shaped guests, see: a) Meyer, C. D.; Joiner, C. S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 1705–1723; b) Yin, J.; Dasgupta, S.; Wu, J. Org. Lett. 2010, 12, 1712–1715; c) Liu, Y.; Li, Z.-T. Aust. J. Chem. 2013, 66, 9–22. 23. Using selenophenol (PhSeH) as the reductant in the same reaction, we obtained only 3% of the desired [2]rotaxane 5 after column chromatography. 24. CCDC-960810 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif. 25. Crystal data for 5: [C59H76O3N6]; Mr = 917.26; orthorhombic; space group P2(1)2(1)2(1); a = 10.4439(2); b = 13.3308(4); c = 39.3404(9) Å.; V = 5477.2(2) Å3 ; ρcalcd = 1.112 g cm-3 ; μ(CuKα) = 0.533 mm-1; T = 200(2) K.; colorless plate; 9955 independent measured reflections; F2 refinement; R1 = 0.0768; wR2 = 0.2108. 26. Possibly because of stronger solvation of the templating Na+ ion in more-polar solvents, a similar “clipping” reaction performed in CD3CN provided no observable signals belonging to the corresponding [2]rotaxane in the 1H NMR spectra of the reactants. 27. For more examples of systems related to peptide rotaxanes, see: a) Bottari, G.; Leigh, D. A.; Perez, E. M. J. Am. Chem. Soc. 2003, 125, 13360–13361; b) Leigh, D. A.; Thomson, A. R. Org. Lett. 2006, 8, 5377–5379; c) Fernandes, A.; Viterisi, A.; Aucagne, V.; Leigh, D. A.; Papot, S. Chem. Commun. 2012, 48, 2083–2085. 28. For recent reviews, see: a) Belowich, M. E.; Stoddart, J. F. Chem. Soc. Rev., 2012, 41, 2003; b) Chambron, J.-C.; Sauvage, J.-P. New J. Chem., 2013, 37, 49; c) Black, S. P.; Sanders, J. K. M.; Stefankiewicz, A. R. Chem. Soc. Rev., 2014, 43, 1861; d) Marti-Centelles, V.; Pandey, M. D.; Burguete, M. I.; Luis, S. V. Chem. Rev., 2015, 115, 8736. 29. a) Thompson, M. C.; Busch, D. H. J. Am. Chem. Soc., 1964, 86, 213; b) Curtis, N. F. Coord. Chem. Rev., 1968, 3, 3; c) Costisor, O.; Linert, W. Metal Mediated Template Synthesis of Ligands, World Scientific Publishing, Singapore, 2004. 30. For reviews, see: a) Champin, B.; Mobian, P.; Sauvage, J.-P. Chem. Soc. Rev., 2007, 36, 358; b) Beves, J. E.; Blight, B. A.; Campbell, C. J.; Leigh, D. A.; McBurney, R. T. Angew. Chem., Int. Ed., 2011, 50, 9260. 31. a) Meyer, M.; Albrecht-Gary, A.-M.; Dietrich-Buchecker, C. 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F. in Advances in Supramolecular Chemistry, ed. Gokel, G. W.; JAI, London, 1999, vol. 5, pp. 1–53. 35. a) Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y.-F.; Bond, A. D.; Sanders, J. K. M. Angew. Chem., Int. Ed., 2004, 43, 1959; b) Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J. K. M.; Stoddart, J. F. J. Am. Chem. Soc., 2004, 126, 9884; c) Lin, Y.-H.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H.; Angew. Chem., Int. Ed., 2013, 52, 10231; d) Wu, K.-D.; Lin, Y.-H.; Lai, C.-C.; Chiu, S.-H. Org. Lett., 2014, 16, 1068; e) Ho, T.-H.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Chem. Eur. J., 2014, 20, 4563; f) Lin, Y.-H.; Lai, C.-C.; Chiu, S.-H. Org. Biomol. Chem., 2014, 12, 2907; g) Wu, Y.-W., Chen, P.-N.; Chang, C.-F.; Lai, C.-C.; Chiu, S.-H. Org. Lett., 2015, 17, 2158; h) Wu, Y.-W.; Tung, S.-T.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Angew. Chem., Int. Ed., 2015, 54, 11745. 36. Tung, S.-T.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Angew. Chem., Int. Ed., 2013, 52, 13269. 37. For chemosensors that can differentiate between Na+ and K+ ions, see: a) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Nieuwenhuizen ,M. Chem. Commun., 1996, 1967; b) Jin, T. Chem. Commun., 1999, 2491; c) He, F.; Tang, Y.; Wang, S.; Li, Y.; Zhu, D. J. Am. Chem. Soc., 2005, 127, 12343; d) Barush, M.; Qin, W.; Vallée, R. A. L.; Beljonne, D.; Rohand, T.; Dehaen, W.; Boens, N. Org. Lett., 2005, 7, 4377; e) Hsueh, S.-Y.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Angew. Chem., Int. Ed., 2007, 46, 2013; f) Wang, X.; Zhu, J.; Smithrud, D. B. J. Org. Chem., 2010, 75, 3358; g) Zhou, X.; Su, F.; Tian, Y.; Youngbull, C.; Johnson, R. H.; Meldrum, D. R. J. Am. Chem. Soc., 2011, 133, 18530; h) Kong, X.; Su, F.; Zhang, L.; Yaron, J.; Lee, F.; Shi, Z.; Tian, Y.; Meldrum, D. R. Angew. Chem., Int. Ed., 2015, 54, 12053. 38. We methylated the [2]catenanes to avoid their slow decomposition in CDCl3; similar tertiary amino derivatives have been found to be much more robust (ref. 20h). For other examples of this methylation method, see: a) Nakazono, K.; Kuwata, S.; Takata, T.; Tetrahedron Lett., 2008, 49, 2397; b) Suzuki, S.; Nakazono, K.; Takata, T. Org. Lett., 2010, 12, 712; c) Lu, T.-W.; Chang, C.-F.; Lai, C.-C.; Chiu, S.-H. Org. Lett., 2013, 15, 5742. | |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/70972 | - |
| dc.description.abstract | 第一部分：以鈉離子為模板經夾鎖法合成非共軛醯胺與尿素之車輪烷研究
我們以鈉離子為模板，引導二胺分子與二醛分子形成具亞胺之大環分子，並且和具有單一尿素基團或醯胺基團之客體分子藉由夾鎖法合成出準車輪烷分子，最後將亞胺鍵還原並純化後可得到穩定且具有胺基的車輪烷分子。 第二部分：尺寸效應對於以鹼金族離子模板導引法合成含寡乙二醇鏈的[2]交環烷效率之影響探討 以鈉離子模板導引法提高合成交環烷產率的策略在此研究中被更進一步地探究，我們變換不同大小的鹼金族離子並與不同長度的含寡乙二醇鏈之二胺分子混合，使其與二醛分子反應，而能成功合成出含不同元件的[2]交環烷，同時比較產率，找出各自最適當大小的鹼金族離子模板。 | zh_TW |
| dc.description.abstract | Part I: Rotaxanes Synthesized Through Sodium-Ion-Templated Clipping of Macrocycles Around Nonconjugated Amide and Urea Functionalities
A single urea or amide functionality in a dumbbell-shaped guest can be “clipped” by a macrocycle generated from a diamine and a dialdehyde through the templating effect of a Na+ ion (see scheme). The resulting imine-containing rotaxanes can then be reduced to allow the isolation of stable amine-based rotaxanes. Part II: Size Effects in the Alkali Metal Ion-Templated Formation of Oligo(Ethylene Glycol)-Containing [2]Catenanes. An investigation into the most suitable alkali metal ions for templating the assembly of [2]catenanes from di-, tri-, and tetra(ethylene glycol)-containing guest diamines and isophthalaldehyde has indicated that Na+, K+, and Rb+ ions are optimal for preparing [2]catenanes containing at least one di(ethylene glycol) unit, two tri(ethylene glycol) units, and at least one tetra(ethylene glycol) unit [in the absence of a di (ethylene glycol) unit], respectively. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-17T04:46:27Z (GMT). No. of bitstreams: 1 ntu-107-F00223145-1.pdf: 12058249 bytes, checksum: 55752020d1fac97f105c592812186f7e (MD5) Previous issue date: 2018 | en |
| dc.description.tableofcontents | 中文摘要 i
英文摘要 ii 論文發表 iii 圖目錄 v 流程目錄 vi 表格目錄 vii 第一章、以鈉離子為模板經夾鎖法合成非共軛醯胺與尿素之車輪烷研究 1 1.1 前言 2 1.2 內鎖型分子：車輪烷 3 1.3 以模板導引法合成車輪烷 4 1.4 研究動機 7 1.5 結果與討論 8 1.6 結論 19 第二章、尺寸效應對於以鹼金族離子模板導引法合成含寡乙二醇鏈的[2]交環烷效率之影響探討 20 2.1 研究動機 21 2.2 中間產物的製備與合成 22 2.3 同交環烷的合成暨不同鹼金族模板的測試 23 2.4 異交環烷的合成暨不同鹼金族模板的測試 27 2.5 交環烷與鹼金族的鍵結常數測量 29 2.6 結論 30 第三章 實驗部分 31 第四章 參考文獻 71 第五章 附錄 77 | |
| dc.language.iso | zh-TW | |
| dc.subject | 鈉離子模板 | zh_TW |
| dc.subject | 車輪烷 | zh_TW |
| dc.subject | 夾鎖法 | zh_TW |
| dc.subject | Rotaxanes | en |
| dc.subject | Sodium-Ion-Templated | en |
| dc.subject | Clipping | en |
| dc.title | 以鈉離子為模板經夾鎖法合成非共軛醯胺與尿素之車輪烷研究 | zh_TW |
| dc.title | Rotaxanes Synthesized Through Sodium-Ion-Templated Clipping of Macrocycles Around Nonconjugated Amide and Urea Functionalities | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 106-2 | |
| dc.description.degree | 博士 | |
| dc.contributor.oralexamcommittee | 陳平,徐秀福,李文山,賴建成 | |
| dc.subject.keyword | 車輪烷,夾鎖法,鈉離子模板, | zh_TW |
| dc.subject.keyword | Rotaxanes,Clipping,Sodium-Ion-Templated, | en |
| dc.relation.page | 168 | |
| dc.identifier.doi | 10.6342/NTU201801636 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2018-08-02 | |
| dc.contributor.author-college | 理學院 | zh_TW |
| dc.contributor.author-dept | 化學研究所 | zh_TW |
| 顯示於系所單位： | 化學系 | |
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