Skip navigation

DSpace

機構典藏 DSpace 系統致力於保存各式數位資料(如:文字、圖片、PDF)並使其易於取用。

點此認識 DSpace
DSpace logo
English
中文
  • 瀏覽論文
    • 校院系所
    • 出版年
    • 作者
    • 標題
    • 關鍵字
    • 指導教授
  • 搜尋 TDR
  • 授權 Q&A
    • 我的頁面
    • 接受 E-mail 通知
    • 編輯個人資料
  1. NTU Theses and Dissertations Repository
  2. 理學院
  3. 化學系
請用此 Handle URI 來引用此文件: http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/68277
完整後設資料紀錄
DC 欄位值語言
dc.contributor.advisor邱勝賢(Sheng-Hsien Chiu)
dc.contributor.authorShun-Te Tungen
dc.contributor.author董順德zh_TW
dc.date.accessioned2021-06-17T02:16:25Z-
dc.date.available2023-01-04
dc.date.copyright2018-01-04
dc.date.issued2017
dc.date.submitted2017-09-29
dc.identifier.citation1. J.-M. Lehn, Science 1993, 260, 1762–1763.
2. a) L. R. Pratt, D. J. Chandler, Chem. Phy. 1977, 67, 3683–3704; b) D. Chandler, Nature 2005, 437, 640–647.
3. G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37–44.
4. a) C. A. Hunter, J. K. M. Sanders, J. Am Chem. Soc. 1990, 112, 5525–5534; b) D. G. Hamilton, J. E. Davies, L. Prodi, J. K. M. Sanders, Chem. Eur. J. 1998, 4, 608–620.
5. a) D. Dougherty, Science 1996, 271, 163–168; b) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303–1324; c) G. W. Gokel, S. L. De Wall, E. S. Meadows, Eur. J. Org. Chem. 2000, 17, 1967–1978; d) G. W. Gokel, L. J. Barbour, R. Ferdani, J. Acc. Chem. Res. 2002, 35, 878–886.
6. J. C. Chambron, S. Chardon-Noblat, C. O. Dietrich-Buchecker, V. Heitz, J. -P. Sauvage, Macrocyle Synthesis 1996, 207–246.
7. a) H. Krause, H. Neusser, J. Chem. Rev. 1994, 94, 1829–1843; b) C. Desfrancois, S. Carles, J. P. Schermann, Chem. Rev. 2000, 100, 3943–3962.
8. G. G. Ferenczy, G. Naray-Sazbo, Chem. Rev. 1995, 95, 829–847.
9. a) C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495–2496; b) D. J. Cram, Angew. Chem. Int. Ed. Engl. 1988, 27, 1009–1020; c) C. J. Pedersen, Angew. Chem. Int. Ed. Engl. 1988, 27, 1021–1027.
10. a) C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495–2496; b) G. W. Gokel, Crown Ethers and Cryptands, Royal Society of Chemistry: London, 1991; c) F. N. Diedrich, Cyclophanes, Royal Society of Chemistry: London, 1991; d) C. D. Gutsche, Calixarenes, Royal Society of Chemistry: London, 1989; e) F. Vögtle; Weber E. (Eds), Host Guest Complex Chemistry: macrocycles Springer: New York, 1985; f) D. J. Cram, J. M. Cram, Container Molecules and Their Guests, Royal Society of chemistry: London, 1994.
11. J. L. Atwood (Ed.), Inclusion Phenomena and Molecular Recognition, Plenum Press: New York, 1988.
12. Please refer to a special issue: Nature 2001, 413, 185–230.
13. a) G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312–1319; b) L. F. lindoy, I. M. Atkinson, Self-assembly in Supramolecular Systems, Royal Society of Chemistry: Cambridge, 2000; c) G. M. Whitesides, B. Grzybowski, Science 2002, 295, 2418–2421; d) M. Boncheva, D. A.Bruzewicz, Pure Appl. Chem. 2003, 75, 621–630.
14. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017–7036.
15. N. H. Evans, P. D. Beer, Chem. Soc. Rev. 2014, 43, 4658–4683.
16. a) E. Wasserman, J. Am. Chem. Soc. 1960, 82, 4433–4434; b) E. Wasserman, Sci. Am. 1962, 207, 94–102.
17. G. Schill, A. Lüttringhaus, Angew. Chem. Int. Ed. 1964, 3, 546–547.
18. a) D. H. Busch, J. Incl. Phen. 1992, 12, 389–395; b) D. H. Busch, N. A. Stephenson, Coord. Chem. Rev. 1990, 100, 119–154.
19. a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J.-P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095–5098; b) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. M. Kern, J. Am. Chem. Soc. 1984, 106, 3043–3045.
20. P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. Int. Ed. 1989, 28, 1396–1399.
21. C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303–5311.
22. D. Armspach, P. R. Ashton, C. P. Moore, N. Spencer, J. F. Stoddart, T. J. Wear, D. J.Williams, Angew. Chem. Int. Ed. 1993, 32, 854–858.
23. M. R. Sambrook, P. D. Beer, J. A. Wisner, R. L. Paul, A. R. Cowley, J. Am. Chem. Soc. 2004, 126, 15364–15365.
24. For reviews, see a) K. Kim, Chem. Soc. Rev. 2002, 31, 96–107; b) K. E. Griffiths, J. F. Stoddart, Pure Appl. Chem. 2008, 80, 485–506; c) Z. Niu, H. W. Gibson, Chem. Rev. 2009, 109, 6024–6046; d) P. Gavina, S. Tatay, Curr. Org. Synth. 2010, 7, 24–43; e) N. H. Evans, P. D. Beer, Self-Assembled Links: Catenanes. Supramolecular Chemistry: From Molecules to Nanomaterials, Wiley, Chichester, UK, 2012; f) V. N. Vukotic, S. J. Loeb, Chem. Soc. Rev. 2012, 41, 5896–5906; g) Y. Tachibana, K. Nakazono, T. Takata, Self-Assembly of Macromolecular Threaded Systems. Supramolecular Chemistry: From Molecules to Nanomaterials, Wiley, Chichester, UK, 2012; h) J.-C. Chambron, J.-P. Sauvage, New J. Chem. 2013, 37, 49–57.
25. For reviews, see a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966–980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930–944; b) G. A. Breault, C. A. Hunter, P. C. Mayers, Tetrahedron 1999, 55, 5265–5293; c) E. R. Kay, D. A. Leigh, Top. Curr. Chem. 2005, 262, 133–177.
26. For reviews, see a) M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369–378; b) F. B. L. Cougnon, J. K. M. Sanders, Acc. Chem. Res. 2012, 45, 2211–2221; c) G. Barin, A. Coskun, M. M. G. Fouda, J. F. Stoddart, ChemPlusChem 2012, 77, 159–185.
27. a) A. Caballero, F. Zapata, N. G. White, P. J. Costa, V. Felix, P. D. Beer, Angew. Chem. 2012, 124, 1912–1916; Angew. Chem. Int. Ed. 2012, 51, 1876–1880; b) G. T. Spence, P. D. Beer, Acc. Chem. Res. 2013, 46, 571–586.
28. For reviews, see a) B. Champin, P. Mobian, J.-P. Sauvage, Chem. Soc. Rev. 2007, 36, 358–366; b) J. E. Beves, B. A. Blight, C. J. Campbell, D. A. Leigh, R. T. McBurney, Angew. Chem. 2011, 123, 9428–9499; Angew. Chem. Int. Ed. 2011, 50, 9260–9327.
29. a) G. W. Gokel, Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991; b) Crown Ethers and Analogous Compounds (Ed.: M. Hiraoka), Elsevier, Amsterdam, 1992; c) M. C. T. Fyfe, J. F. Stoddart in Advances in Supramolecular Chemistry, Vol. 5 (Ed.: G. W. Gokel), JAI, London, 1999.
30. Y.-L. Huang, W.-C. Hung, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Angew. Chem. 2007, 119, 6749–6753; Angew. Chem. Int. Ed. 2007, 46, 6629–6633.
31. In previous studies we combined one diethylene glycol chain with two aryl rings to develop a new class of “oxygen-deficient” hosts for the binding of dibenzylammonium ions; see a) P.-N. Cheng, P.-Y. Huang, W.-S. Li, S.-H. Ueng, W.-C. Hung, Y.-H. Liu, C.-C. Lai, S.-M. Peng, I. Chao, S.-H. Chiu, J. Org. Chem. 2006, 71, 2373–2383; b) N.-C. Chen, P.-Y. Huang, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Chem. Commun. 2007, 4122–4124; c) Y.-C. You, M.-C. Tzeng, C.-C. Lai, S.-H. Chiu, Org. Lett. 2012, 14, 1046–1049.
32. a) S. H. Strauss, Chem. Rev. 1993, 93, 927–942; b) I. Krossing, I. Raabe, Angew. Chem. 2004, 116, 2116–2142; Angew. Chem. Int. Ed. 2004, 43, 2066–2090; c) J. Pérez, L. Riera, L. Ion, V. Riera, K. M. Anderson, J. W. Steed, D. Miguel, Dalton Trans. 2008, 878–886; d) C. Gaeta, F. Troisi, P. Neri, Org. Lett. 2010, 12, 2092–2095; e) N.-C. Chen, C.-J. Chuang, L.-Y. Wang, C.-C. Lai, S.-H. Chiu, Chem. Eur. J. 2012, 18, 1896–1900; f) L.-Y. Wang, J.-L. Ko, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Chem. Eur. J. 2013, 19, 8850–8860; g) Y.-H. Lin, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Angew. Chem. 2013, 125, 10421–10426; Angew. Chem. Int. Ed. 2013, 52, 10231–10236.
33. For examples of using imine formation to construct rotaxanes from dibenzylammonium or pyridinium ion containing dumbbell-shaped guests, see a) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922–1927; Angew. Chem. Int. Ed. 2001, 40, 1870–1875; b) K. C.-F. Leung, F. Arico, S. J. Cantrill, J. F. Stoddart, J. Am. Chem. Soc. 2005, 127, 5808–5810; c) J. Wu, K. C.-F. Leung, J. F. Stoddart, Proc. Natl. Acad. Sci. USA 2007, 104, 17266–17271; d) Z. Li, W. Liu, J. Wu, S. H. Liu, J. Yin, J. Org. Chem. 2012, 77, 7129–7135; e) A. Pun, D. A. Hanifi, G. Kiel, E. O’Brien, Y. Liu, Angew. Chem. 2012, 124, 13296–13299; Angew. Chem. Int. Ed. 2012, 51, 13119–13122; f) Y. Liu, Z.-T. Li, Aust. J. Chem. 2013, 66, 9–22.
34. The same reagent has been used to “fix” an imine-based [2]rotaxane; see S. J. Cantrill, S. J. Rowan, J. F. Stoddart, Org. Lett. 1999, 1, 1363–1366.
35. The phenanthroline motif of a [2]catenane exhibits enhanced basicity arising from its topology; see M. Cesario, C. O. Dietrich, A. Edel, J. Guilhem, J.-P. Kintzinger, C. Pascard, J.-P. Sauvage, J. Am. Chem. Soc. 1986, 108, 6250–6254.
dc.identifier.urihttp://tdr.lib.ntu.edu.tw/jspui/handle/123456789/68277-
dc.description.abstract第一部分:以鈉離子導引兩條二乙二醇鏈正交排列並合成[2]交環烷
如欲有效率地建構[2]交環烷,常藉由模板導引法將分子個別的前驅物元件適當排列,然而並沒有任何以鹼金屬離子為模板的先例。在本文中,我們報導了以五個元件 (兩個二醛分子、兩個二胺分子、一個鈉離子) 自組裝合成[2]交環烷。這種簡單而有效的合成策略能將鈉離子作為模板,使含有二乙二醇鏈的二胺分子兩兩正交排列,並與二醛分子反應生成[2]交環烷。利用硼氫化鈉還原不穩定的亞胺鍵,以分離並鑑定穩定的[2]交環烷。

第二部分:環狀[2]交環烷二聚體之合成研究
先前我們報導了以鈉離子為模板,使含有二乙二醇鏈的二胺分子兩兩正交排列,並與二醛分子反應生成[2]交環烷。於此,我們希望能延伸此系統,設計具有特定角度的四醛分子,搭配二胺分子與鈉離子模板,以動態亞胺鍵一鍋化自組裝成環狀[2]交環烷寡聚體。利用硼氫化鈉還原不穩定的亞胺鍵,並甲基化所得的二級胺,以分離並鑑定由共價鍵建構且穩定的環狀[2]交環烷二聚體。
zh_TW
dc.description.abstractPart I : Synthesis of a [2]Catenane from the Sodium Ion Templated Orthogonal Arrangement of Two Diethylene Glycol.
An important feature for the efficient construction of a [2]catenane is the appropriate alignment of the individual precursor molecular components by template-directed synthesis. However, we were unaware of any examples of the use of alkali metal ions as a template. Herein, we report the synthesis of a [2]catenane from five components (two diamines, two dialdehydes, one Na+ ion). This simple and efficient synthesis strategy makes use of a Na+ ion as a template to align two di(ethylene glycol)-containing diamines in an orthogonal manner, which can then react with two units of dialdehyde to generate [2]catenanes. NaBH4 mediated reduction of the labile imino bonds enabled the isolation and characterization of the [2]catenane as a stable compound.
Part II : Synthesis of a Cyclic [2]Catenane Dimer.
Previously, we reported that Na+ ions can template the orthogonal alignment of two di(ethylene glycol)-containing diamines, which can then react with two units of dialdehyde to generate [2]catenanes. We wished to extend this concept by applying the tetraaldehyde with specific angle for the corresponding reaction with diamine and Na+ ions to dynamically synthesis cyclic [2]catenane oligomers. NaBH4 mediated reduction of the labile imino bonds of these cyclic [2]catenane oligomers, followed by methylation of the resulting secondary amino groups enabled the isolation and characterization of a dimeric cyclic [2]catenane as stable, covalently linked compounds.
en
dc.description.provenanceMade available in DSpace on 2021-06-17T02:16:25Z (GMT). No. of bitstreams: 1
ntu-106-D01223137-1.pdf: 6584059 bytes, checksum: 9561707a793bea364aecc436ee101477 (MD5)
Previous issue date: 2017
en
dc.description.tableofcontents口試委員會審定...........................................I
中文摘要...............................................II
英文摘要...............................................III
論文發表................................................V
目錄..................................................VII
圖目錄.................................................IX
流程目錄...............................................XI
表目錄................................................XII
第一章、緒論.............................................1
1.1 超分子化學簡介...................................1
1.2 主客化學與冠醚分.................................2
1.3 交環烷分子 (catenane) 簡介.......................4
1.4 早期交環烷的合成.................................5
1.5 以模板導引法合成交環烷............................6
第二章、以鈉離子導引兩條二乙二醇鏈正交排列並合成[2]交環烷...12
2.1 研究動機........................................13
2.2 實驗結果與討論..................................14
2.3 結論...........................................20
第三章、環狀[2]交環烷二聚體之合成研究.....................21
3.1 研究動機........................................22
3.2 60度四醛分子 7 之合成...........................24
3.3 實驗結果與討論..................................25
3.4 結論...........................................30
第四章、實驗部分........................................31
第五章、參考資料........................................37
第六章、附錄............................................42
dc.language.isozh-TW
dc.subject交環烷zh_TW
dc.subject鈉離子模板zh_TW
dc.subject自組裝zh_TW
dc.subjectcatenaneen
dc.subjectsodium Ion templateden
dc.subjectself-assemblyen
dc.title以鈉離子導引兩條二乙二醇鏈正交排列並合成[2]交環烷zh_TW
dc.titleSynthesis of a [2]Catenane from the Sodium Ion Templated Orthogonal Arrangement of Two Diethylene Glycolen
dc.typeThesis
dc.date.schoolyear106-1
dc.description.degree博士
dc.contributor.oralexamcommittee陳平(Richard P. Cheng),徐秀福(Hsiu-Fu Hsu),李文山(Wen-Shan Li),賴建成(Chien-Chen Lai)
dc.subject.keyword交環烷,鈉離子模板,自組裝,zh_TW
dc.subject.keywordcatenane,sodium Ion templated,self-assembly,en
dc.relation.page56
dc.identifier.doi10.6342/NTU201704228
dc.rights.note有償授權
dc.date.accepted2017-09-29
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

文件中的檔案:
檔案 大小格式 
ntu-106-1.pdf
  未授權公開取用
6.43 MBAdobe PDF
顯示文件簡單紀錄


系統中的文件,除了特別指名其著作權條款之外,均受到著作權保護,並且保留所有的權利。

社群連結
聯絡資訊
10617臺北市大安區羅斯福路四段1號
No.1 Sec.4, Roosevelt Rd., Taipei, Taiwan, R.O.C. 106
Tel: (02)33662353
Email: ntuetds@ntu.edu.tw
意見箱
相關連結
館藏目錄
國內圖書館整合查詢 MetaCat
臺大學術典藏 NTU Scholars
臺大圖書館數位典藏館
本站聲明
© NTU Library All Rights Reserved