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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 方俊民(Jim-Min Fang) | |
dc.contributor.author | "Da-Ming, Wang" | en |
dc.contributor.author | 王大明 | zh_TW |
dc.date.accessioned | 2021-06-13T03:15:54Z | - |
dc.date.available | 2006-07-31 | |
dc.date.copyright | 2006-07-31 | |
dc.date.issued | 2006 | |
dc.date.submitted | 2006-07-31 | |
dc.identifier.citation | 1. Valeur, B. in Molecular Fluorescence: Principles and Applications. 2002, 288.
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Convenient and Efficient Tosylation of Oligoethylene Glycols and the Related Alcohols in Tetrahydrofuran-Water in the Presence of Sodium Hydroxide. 21. Brockmann, T. W.; Tour, J. M. J. Am. Chem. Soc. 1995, 117, 4437. Synthesis and Properties of Low-Bandgap Zwitterionic and Planar Conjugated Pyrrole-Derived Polymeric Sensor. Reversible Optical Absorption Maxima from the UV to the Near-IR. 22. 黃如慧,台灣大學化學研究所博士論文,2004 23. Davis, A. P.; James, T. D. in Functional Synthetic Receptors, Schrader, T., Hamilton, A. D., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 45. 24. Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H, J. Am. Chem. Soc. 1988, 110, 634-635. Polar Host-Guest Interaction. Binding of Nonionic Polar Compounds with a Resorcinol-Aldehyde Cyclooligomer as a Lipophilic Polar Host. 25. Bhattarai, K. M., Bonar-Law, R. P. ; Davis, A. P., Murray, B. A. J. Chem. Soc. Chem. Commun. 1992, 752. Diastereo- and Enantio-Selective Binding of Octyl Glucosides by an Artificial Receptor. 26. (a) Mizutani, T.; Murakami, T.; Matsumi, N.; Kurahashi, T.; Ogoshi, H. J. Chem. Soc. Chem. Commun. 1995, 1257. Molecular Recognition of Carbohydrates by Functionalized Zinc Porphyrins. (b) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001. Molecular Recognition of Carbohydrates by Zinc Porphyrins: Lewis Acid/Lewis Base Combinations as A Dominant Factor for Their Selectivity. 27. (a) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416. Molecular Recognition of beta-Ribofuranosides by Synthetic Polypyridine-Macrocyclic Receptors. (b) Inouye, M.; Chiba, J. J. Org. Chem. 1999, 64, 8170-8176. Glucopyranoside Recognition by Polypyridine-Macrocyclic Receptors Possessing a Wide Cavity with a Flexible Linkage. 28. Davis, A. P.; Wareham, R. Angew. Chem. Int. Ed. 1998, 37, 2270. A Tricyclic Polyamide Receptor for Carbohydrates in Organic Media. 29. (a) Liao, J. H.; Chen, C. T.; Chou, H. C.; Cheng, C. C.; Chou, P. T.; Fang, J. M.; Slanina, Z.; Chow, T. J. Org. Lett. 2002, 4, 3107-3110. 2,7-Bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine: An Ultrasensitive Fluorescent Probe for Glucopyranoside. (b) Fang, J. M.; Selvi, S.; Liao, J. H., Slanina, Z.; Chen, C. T.; Chou, P. T. J. Am. Chem. Soc. 2004, 126, 3559. Fluorescent and Circular Dichroic Detection of Monosaccharides by Molecular Sensors: Bis[(Pyrrolyl)ethynyl]naphthyridine and Bis[(Indolyl)ethynyl]naphthyridine. 30. Foster, A. B.; Stacey, M. J. Chem. Soc. 1955, 1778-1781. Ionophoresis of Carbohydrates. II. Pyranose and Furanose Derivs. of D-Glucose. 31. Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769. Polyol Complexes and Structure of the Benzeneboronate Ion. 32. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Specific Complexation with Mono- and Disaccharides that Can Be Detected by Circular Dichroism. 33. (a) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc. Chem. Commun. 1994, 477. Novel Photoinduced Electron-Transfer Sensor for Saccharides Based on the Interaction of Boronic Acid and Amine. (b) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem. Int. Ed. 1994, 33, 2287. A Glucose-Specific Molecular Fluorescence sensor. 34. Kukrer, B.; Akkaya, E. U. Tetrahedron Lett. 1999, 40, 9125. Red to Near IR Fluorescent Signalling of Carbohydrates. 35. Adhikari, D. P.; Heagy, M. D. Tetrahedron Lett. 1999, 40, 7893. Fluorescent Chemosensor for Carbohydrates which Shows Large Change in Chelation-Enhanced Quenching. 36. Ward, C. J.; Patel, P.; James, T. D. J. Chem. Soc., Perkin Trans. 1 2002, 462. Boronic Acid Appended Azo Dyes-Colour Sensors for Saccharides. 37. Springsteen, G.; Wang, B. Chem. Commun. 2001, 1608. Alizarin Red S. as A General Optical Reporter for Studying the Binding of Boronic Acids with Carbohydrates. 38. Bahr, A.; Felber, B.; Schneider, K., Diederich, F. Helv. Chim. Acta. 2000, 83, 1346. Dendritic, 1,1’-Binaphthalene-Derived Cleft-Type Receptors (Dendroclefts) for the Molecular Recognition of Pyranosides. 39. Bhattarai, K. M.; Davis, A. P.; Perry, J. J.; Walter, C. J.; Menzer, S.; Walliams, D. J. J. Org. Chem. 1997, 62, 8463. A New Generation of 'Cholaphanes': Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility. 40. Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. USA 2002, 99, 4863. Phase Transfer of Monosaccharides through Noncovalent Interactions: Selective Extraction of Glucose by a Lipophilic Cage Receptor. 41. Velasco, T.; Lecollinet, G.; Ryan, T.; Davis, A. P. Org. Biomol. Chem. 2004, 2, 645. Tuning Selectivity in Macrotricyclic Carbohydrate Receptors; CH N Mutations in Aromatic Spacers. 42. Klein, E.; Crump, M. P.; Davis, A. P. Angew. Chem. Int. Ed. 2005, 44, 298. Carbohydrate Recognition in Water by a Tricyclic Polyamide Receptor. 43. (a) Newkome, G. R.; Garbis, S. J.; Majestic, V. K.; Fronczek, F. R.; Chiari, G. J. Org. Chem. 1981, 46, 833. Chemistry of Heterocyclic Compounds. 61. Synthesis and Conformational Studies of Macrocycles Possessing 1,8- or 1,5-Naphthyridino Subunits Connected by Carbon-Oxygen Bridges. (b) Ziessel, R.; Suffert, J.; Youinou, M.-T. J. Org. Chem. 1996, 61, 6535. General Method for the Preparation of Alkyne-Functionalized Oligopyridine Building Blocks. 44. Anderson, H. J.; Lee, S.-F. Can. J. Chem. 1965, 43, 409. Pyrrole Chemistry IV. The Preparation and Some Reactions of Brominated Pyrrole Derivatives. 45. Abell, A. D.; Nabbs, B. K.; Battersby, A. R. J. Am. Chem. Soc. 1998, 120, 1741. Synthesis and Properties of Ring-Deactivated Deuterated (Hydroxymethyl)pyrroles. 46. Chen, W.; Cava, M. P. Tetrahedron Lett. 1987, 28, 6025. Convenient Synthetic Equivalents of 2-Lithiopyrrole and 2,5-Dilithiopyrrole. 47. (a) Freed, J. D.; Hart, D. J.; Magomedov, N. A. J. Org. Chem. 2001, 66, 839. Trapping of the Putative Cationic Intermediate in the Morin Rearrangement with Carbon Nucleophiles. (b) Be´langer, G.; Larouche-Gauthier, R.; Me´nard, F.; Nantel, M.; Barabe, F. J. Org. Chem. 2006, 71, 704. Intramolecular Additions of Various pi-Nucleophiles to Chemoselectively Activated Amides and Application to the Synthesis of (±)-Tashiromine. (c) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315. Solvophobically Driven pi-Stacking of Phenylene Ethynylene Macrocycles and Oligomers. | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/31616 | - |
dc.description.abstract | 本篇論文主要分為二部份,分別是水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識,以及口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試。
第一部份︰水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識 在第一部分的研究中,藉著在吡咯環上引進水溶性的ethylene glycol基團以增進BPBP的水溶性,以便於在水溶液中對金屬離子的檢測及研究。我們成功地合成出水溶性BPBP衍生物,其在幾乎為水的條件下 (氰甲烷/水 = 1: 99 ),仍然對銀、銅以及汞離子有辨識效果,且與金屬離子結合後紫外-可見光吸收會造成紅位移的變化。 第二部份︰口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試 口奈啶-双吡咯化合物BPN為本實驗室開發出對醣苷有辨識能力的螢光分子,其具有極佳的光物理性質使得BPN在二氯甲烷下,對正辛烷基葡萄糖苷的螢光偵測極限可達100 pM,但其缺點為水溶性太差,因此醣需經長碳鏈衍生化以增加其對有機溶劑的溶解度以進行檢測。在第二部份中,我們以BPN為主體,藉著引入水溶性的ethylene glycol基團以增進BPN的水溶性。另外也嘗試將BPN應用至兩相系統的萃取中,但空白實驗的結果顯示即使是少量的水藉著萃取溶進二氯甲烷中,也會對BPN的螢光強度變化造成干擾。 | zh_TW |
dc.description.abstract | This thesis consists of two parts. The first part is to prepare water soluble bispyrrole-bipyridine derivatives for recognition of metal ions in water; the second part is to synthesize water soluble bispyrrole-naphthyridine derivatives, and the binding study in two-phase system is also attempted.
Part I: Preparation of water soluble bispyrrole-bipyridine derivatives for recognition of metal ions in water By introduction of ethylene glycol moiety to the pyrrole ring of BPBP molecule, the solubility of such BPBP derivative in water is enhanced, thus sensing metal ions in water becomes possible. The synthesis of a water-soluble BPBP derivative is carried out, and the BPBP compound showed binding affinity toward silver(I), copper(II), and mercury(II) ions in aqueous solution ( CH3CN/H2O = 1: 99 ). The BPBP receptor shows shifts in the UV-Vis spectra on binding with appropriate metal ions. Part II: Synthesis of water soluble bispyrrole-naphthyridine derivatives and the binding study in two-phase system Bispyrrole-naphthyridine molecule BPN (2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine) is a fluorescent molecule designed to bind selectively with octyl glucopyranoside in our lab. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of 100 pM. However, BPN has poor water solubility, thus we have to use alkyl glucopyranoside for the binding study in organic solvents. We thus attempted to incorporate ethylene glycol group to BPN to render an enhanced solubility in water. We also attempted to examine the binding of BPN with sugar in two-phase system. However, the blank tests showed that even little water extracted in dichloromethane would interfere with the fluorescence intensity of BPN. | en |
dc.description.provenance | Made available in DSpace on 2021-06-13T03:15:54Z (GMT). No. of bitstreams: 1 ntu-95-R93223027-1.pdf: 1220027 bytes, checksum: f133929ac8c6f2584fdc095e607d3f08 (MD5) Previous issue date: 2006 | en |
dc.description.tableofcontents | 目錄
目錄........................................................ I 圖目錄...................................................... III 表目錄...................................................... V 流程目錄.................................................... VI 簡稱用語對照表.............................................. VII 中文摘要.................................................... VIII 英文摘要.................................................... X 第一部份:水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識..........................................1 壹、 緒論................................................... 1 一、 前言.............................................. 1 二、 光誘導電子轉移機制................................ 2 三、 光誘導電荷轉移機制................................ 7 貳、 結果與討論............................................. 13 一、 水溶性受體分子的構想與合成........................ 13 二、 BPBP對金屬離子的測試 ........................... 17 三、 水溶性BPBP衍生物對金屬離子的測試結果............ 21 四、 推測的結合模式.................................... 33 參、 結論................................................... 36 第二部份:口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試..37 壹、 緒論................................................... 37 一、 醣類分子辨識...................................... 37 二、 在兩相系統的醣類辨識.............................. 43 貳、 結果與討論............................................. 49 一、 水溶性BPN受體的合成嘗試......................... 49 二、 BPN應用於兩相系統的嘗試.......................... 56 實驗部份..................................................... 59 壹、 一般敘述................................................ 59 一、 測試及實驗儀器.................................... 59 二、 溶劑、試劑之前處理................................ 60 三、 實驗前準備要項.................................... 61 四、 紫外-可見光光譜及螢光光譜實驗一般步驟............. 61 貳、 實驗步驟與光譜數據..................................... 64 參考文獻.................................................... 81 附錄........................................................ 91 圖目錄 圖一 光誘導電子轉移機制........................................3 圖二 光誘導電荷轉移機制........................................8 圖三 水溶性BPBP衍生物分子結構圖..............................13 圖四 在氰甲烷下BPBP與10當量不同金屬離子的紫外-可見光光譜圖..17 圖五 在氰甲烷下BPBP與銅離子的紫外-可見光光譜滴定圖...........18 圖六 在氰甲烷溶液下BPBP與銅離子的Job’s plot圖................. 19 圖七 在氰甲烷溶液下OEG-BPBP與10當量不同金屬離子的紫外-可見光光譜圖........................................................ 22 圖八 在1 % 氰甲烷 / 去離子水溶液下OEG-BPBP與10當量不同金屬離子的紫外-可見光光譜圖.........................................23 圖九 HEPES分子結構圖.........................................24 圖十 在1 % 氰甲烷 / HEPES 緩衝溶液下OEG-BPBP與10當量不同金屬離子的紫外-可見光光譜圖.......................................24 圖十一 在1 % 氰甲烷 / 去離子水溶液下OEG-BPBP與銅離子的紫外-可見光光譜滴定圖................................................25 圖十二 在1 % 氰甲烷 / 去離子水溶液下OEG-BPBP與銅離子的Job’s plot圖........................................................................................26 圖十三 在1 % 氰甲烷 / HEPES 緩衝溶液下OEG-BPBP與銅離子的紫外-可見光光譜滴定圖..............................................27 圖十四 在1 % 氰甲烷 / 去離子水溶液下OEG-BPBP與汞離子的紫外-可見光光譜滴定圖................................................28 圖十五 在1 % 氰甲烷 / HEPES 緩衝溶液下OEG-BPBP與汞離子的紫外-可見光光譜滴定圖..............................................29 圖十六 在1 % 氰甲烷 / 去離子水溶液下OEG-BPBP與汞離子的Job’s plot圖............................................................30 圖十七 在1 % 氰甲烷 / 去離子水溶液下OEG-BPBP與銀離子的紫外-可見光光譜滴定圖................................................31 圖十八 以Specfit/32軟體計算OEG-BPBP在1 % 氰甲烷 / 去離子水溶液下與銀離子滴定過程中物種[MLH]形成或消失的百分比...............32 圖十九 BPBP與單一金屬離子推測可能配位模式,(L)x表示可能的配位子(如CH3CN)..................................................33 圖二十 OEG-BPBP與金屬 (銅、汞) 離子推測可能配位模式..........34 圖二十一 OEG-BPBP與銀離子推測可能配位模式,(L)x表示可能的配位子(如CH3CN)...............................................34 圖二十二 水溶性BPN分子結構圖.................................49 圖二十三 BPN與醣類萃取後的紫外-可見光光譜....................57 圖二十四 BPN與醣類萃取後的螢光光譜...........................57 表目錄 表一 OEG-BPBP在不同pH值溶液下滴定後所形成物種的結合常數 ( logKass ) 比較.................................................30 流程目錄 流程一 6, 6’-二溴-2, 2'-二吡啶的合成..............................14 流程二 2-Ethynylpyrrole-1-carboxylic acid tert-butyl ester之合成........15 流程三 triethylene glycol monomethyl toslate的合成...................15 流程四 BPBP水溶性衍生物1之製備..............................16 流程五 水溶性BPN衍生物的逆合成分析...........................50 流程六 2,7-二氯-1,8-口奈啶的合成步驟.........................51 流程七 合成末端為氫的炔分子的預期步驟......................... 52 流程八 溴化2-pyrrolecarboxyaldehyde的嘗試........................53 流程九 在吡咯上修飾ethylene glycol的嘗試(一).....................53 流程十 在吡咯上修飾ethylene glycol的嘗試(二).....................54 流程十一 在吡咯上修飾triethylene glycol的可能嘗試路徑.............55 流程十二 受體分子BPN的合成...................................56 | |
dc.language.iso | zh-TW | |
dc.title | 合成水溶性含氮雜環化合物及其在分子辨識上之應用(ㄧ)水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識(二)口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試 | zh_TW |
dc.title | Synthesis of Water Soluble Nitrogen Heterocyclic Compounds for Applications in Molecular Recognition
I. Preparation of Water Soluble Bispyrrole-bipyridine Derivatives for Recognition of Metal Ions in Water II Synthesis of Water Soluble Bispyrrole-naphthyridine Derivatives and The Binding Study in Two-Phase System | en |
dc.type | Thesis | |
dc.date.schoolyear | 94-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 周必泰(Pi-Tai Chou),鍾文聖(Wen-Sheng Chung) | |
dc.subject.keyword | 水溶性,分子辨識,兩相系統, | zh_TW |
dc.subject.keyword | Water-Soluble,Molecular Recognition,Two-Phase System, | en |
dc.relation.page | 92 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2006-07-31 | |
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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