請用此 Handle URI 來引用此文件：
http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/72033完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 楊吉水(Jye-Shane Yang) | |
| dc.contributor.author | Chin-Han Lee | en |
| dc.contributor.author | 李金翰 | zh_TW |
| dc.date.accessioned | 2021-06-17T06:20:03Z | - |
| dc.date.available | 2023-08-21 | |
| dc.date.copyright | 2018-08-21 | |
| dc.date.issued | 2018 | |
| dc.date.submitted | 2018-08-19 | |
| dc.identifier.citation | 1. Beaufils, J. P.; Hennion, M. C.; Rosset, R., Neutron Scattering Study of Alkyl Chain Motion on Reversed-Phase Liquid Chromatographic Packings. Anal. Chem. 1985, 57 (13), 2593-2596.
2. Wang, H.; Zhuang, J.; Raghupathi, K. R.; Thayumanavan, S., A Supramolecular Dissociation Strategy for Protein Sensing. Chem Commun 2015, 51 (97), 17265-17268. 3. Tou, S. L.; Huang, G. J.; Chen, P. C.; Chang, H. T.; Tsai, J. Y.; Yang, J. S., Aggregation-Induced Emission of GFP-Like Chromophores via Exclusion of Solvent-Solute Hydrogen Bonding. Chem Commun 2014, 50 (5), 620-622. 4. Kroeze, J. E.; Hirata, N.; Koops, S.; Nazeeruddin, M. K.; Schmidt-Mende, L.; Gratzel, M.; Durrant, J. R., Alkyl Chain Barriers for Kinetic Optimization in Dye-Sensitized Solar Cells. J. Am. Chem. Soc. 2006, 128 (50), 16376-16383. 5. Jiang, X.; Marinado, T.; Gabrielsson, E.; Hagberg, D. P.; Sun, L.; Hagfeldt, A., Structural Modification of Organic Dyes for Efficient Coadsorbent-Free Dye-Sensitized Solar Cells. J. Phys. Chem. C 2010, 114 (6), 2799-2805. 6. Poirier, G. E.; Pylant, E. D., The Self-Assembly Mechanism of Alkanethiols on Au(111). Science 1996, 272 (5265), 1145-1148. 7. Yang, J. S.; Ko, C. W., Pentiptycene Chemistry : New Pentiptycene Building Blocks Derived from Pentiptycene Quinones. J. Org. Chem. 2006, 71 (2), 844-847. 8. Yang, J.-S.; Swager, T. M., Fluorescent Porous Polymer Films as TNT Chemosensors: Electronic and Structural Effects. J. Am. Chem. Soc. 1998, 120 (46), 11864-11873. 9. Tsumura, A.; Koezuka, H.; Ando, T., Macromolecular Electronic Device: Field‐effect Transistor With a Polythiophene Thin Film. Appl. Phys. Lett. 1986, 49 (18), 1210-1212. 10. Babel, A.; Jenekhe, S. A., Alkyl Chain Length Dependence of the Field-Effect Carrier Mobility in Regioregular Poly(3-alkylthiophene)s. Synth. Met. 2005, 148 (2), 169-173. 11. Salleo, A., Charge Transport in Polymeric Transistors. Mater. Today 2007, 10 (3), 38-45. 12. Saito, S.; Nakakura, K.; Yamaguchi, S., Macrocyclic Restriction with Flexible Alkylene Linkers : A Simple Strategy to Control the Solid-State Properties of Pi-Conjugated Systems. Angew. Chem. Int. Ed. Engl. 2012, 51 (3), 714-717. 13. Ding, L.; Li, H.-B.; Lei, T.; Ying, H.-Z.; Wang, R.-B.; Zhou, Y.; Su, Z.-M.; Pei, J., Alkylene-Chain Effect on Microwire Growth and Crystal Packing of π-Moieties. Chem. Mater. 2012, 24 (10), 1944-1949. 14. Kim, Y.; Zhu, Z.; Swager, T. M., Scanning Tunneling Microscopy of Prochiral Anthracene Derivatives on Graphite: Chain Length Effects on Monolayer Morphology. J. Am. Chem. Soc. 2004, 126 (2), 5318. 15. Inokuchi, H.; Saito, G.; Wu, P.; Seki, K.; Tang, T. B.; Mori, T.; Imaeda, K.; Enoki, T.; Higuchi, Y.; Inaka, K.; Yasuoka, N., A Novel Type of Organic Semiconductors. Molecular Fastener. Chem. Lett. 1986, 15 (8), 1263-1266. 16. Ebata, H.; Izawa, T.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Yui, T., Highly Soluble [1]benzothieno[3,2-b]benzothiophene (BTBT) Derivatives for High-Performance, Solution-Processed Organic Field-Effect Transistors. J. Am. Chem. Soc. 2007, 129 (51), 15732-15733. 17. Kitamura, C.; Ohara, T.; Kawatsuki, N.; Yoneda, A.; Kobayashi, T.; Naito, H.; Komatsu, T.; Kitamura, T., Conformational Polymorphism and Optical Properties in the Solid State of 1,4,7,10-tetra(n-butyl)tetracene. CrystEngComm 2007, 9 (8), 644. 18. Kitamura, C.; Abe, Y.; Ohara, T.; Yoneda, A.; Kawase, T.; Kobayashi, T.; Naito, H.; Komatsu, T., Synthesis and Crystallochromy of 1,4,7,10-tetraalkyltetracenes: Tuning of Solid-State Optical Properties of Tetracenes by Alkyl Side-Chain Length. Chem. Eur. J. 2010, 16 (3), 890-898. 19. Wang, X. Y.; Lin, H. R.; Lei, T.; Yang, D. C.; Zhuang, F. D.; Wang, J. Y.; Yuan, S. C.; Pei, J., Azaborine Compounds for Organic Field-Effect Transistors : Efficient Synthesis, Remarkable Stability, and BN Dipole Interactions. Angew. Chem. Int. Ed. Engl. 2013, 52 (11), 3117-3120. 20. Nagarajan, K.; Gopan, G.; Cheriya, R. T.; Hariharan, M., Long Alkyl Side-Chains Impede Exciton Interaction in Organic Light Harvesting Crystals. Chem Commun 2017, 53 (53), 7409-7411. 21. Chen, X.; Zhang, X.; Zhang, G., Wide-Range Thermochromic Luminescence of Organoboronium Complexes. Chem Commun 2015, 51 (1), 161-163. 22. Mutai, T.; Satou, H.; Araki, K., Reproducible On-Off Switching of Solid-State Luminescence by Controlling Molecular Packing Through Heat-Mode Interconversion. Nat Mater 2005, 4 (9), 685-687. 23. Xiong, Y.; Ma, Y.; Yan, X.; Yin, G.; Chen, L., Significant Effect of Alkyl Chain Length on Fluorescent Thermochromism of 9,10-bis(p-alkoxystyryl)anthracenes. RSC Advances 2015, 5 (66), 53255-53258. 24. Löwe, C.; Weder, C., Oligo(p-phenylene vinylene) Excimers as Molecular Probes: Deformation-Induced Color Changes in Photoluminescent Polymer Blends. Adv. Mater. 2002, 14 (22), 1625-1629. 25. Sagara, Y.; Mutai, T.; Yoshikawa, I.; Araki, K., Material Design for Piezochromic Luminescence : Hydrogen-Bond-Directed Assemblies of a Pyrene Derivative. J. Am. Chem. Soc. 2007, 129 (6), 1520-1521. 26. Ito, H.; Muromoto, M.; Kurenuma, S.; Ishizaka, S.; Kitamura, N.; Sato, H.; Seki, T., Mechanical Stimulation and Solid Seeding Trigger Single-Crystal-to-Single-Crystal Molecular Domino Transformations. Nat Commun 2013, 4, 2009. 27. Ge, C.; Liu, J.; Ye, X.; Han, Q. X.; Zhang, L. L.; Cui, S. Y.; Guo, Q.; Liu, G. F.; Liu, Y.; Tao, X. T., Visualization of Single-Crystal-to-Single-Crystal Phase Transition of Luminescent Molecular Polymorphs. J. Phys. Chem. C 2018, 122 (27), 15744-15752. 28. Yang, W.; Liu, C. L.; Lu, S.; Du, J. Y.; Gao, Q. Y.; Zhang, R. H.; Liu, Y.; Yang, C. Y., AIE-Active Smart Cyanostyrene Luminogens: Polymorphism-Dependent Multicolor Mechanochromism. J. Mater. Chem. C 2018, 6 (2), 290-298. 29. Takahashi, E.; Takaya, H.; Naota, T., Dynamic Vapochromic Behaviors of Organic Crystals Based on the Open-Close Motions of S-Shaped Donor-Acceptor Folding Units. Chem. Eur. J. 2010, 16 (16), 4793-4802. 30. Koenig, M.; Storti, B.; Bizzarri, R.; Guldi, D. M.; Brancato, G.; Bottari, G., A Fluorescent Molecular Rotor Showing Vapochromism, Aggregation-Induced Emission, and Environmental Sensing in Living Cells. J. Mater. Chem. C 2016, 4 (14), 3018-3027. 31. Heller, E.; Schmidt, G. M. J., Topochemistry. Part XXXIII. The Solid-State Photochemistry of Some Anthracene Derivatives. Isr. J. Chem. 1971, 9 (4), 449-462. 32. Becker, H. D.; Langer, V.; Becker, H. C., Photochemistry of 9-Benzoylanthracene. J. Org. Chem. 1993, 58 (23), 6394-6396. 33. Förster, T., Excimers. Angew. Chem. Int. 1969, 8 (5), 333-343. 34. Jones, P. F.; Nicol, M., Excimer Emission of Naphthalene, Anthracene, and Phenanthrene Crystals Produced by Very High Pressures. J. Chem. Phys. 1968, 48 (12), 5440-5447. 35. Birks, J. B.; Christophorou, L. G., Excimer Fluorescence Spectra of Pyrene Derivatives. Spectrochim. Acta 1963, 19 (2), 401-410. 36. Caldwell, R. A.; Creed, D., Exciplex Intermediates in [2 + 2] Photocycloadditions. Acc. Chem. Res. 1980, 13 (2), 45-50. 37. Saltiel, J.; Townsend, D. E.; Watson, B. D.; Shannon, P.; Finson, S. L., Concerning the Participation of the Anthracene/N,N-dimethylaniline Exciplex in Anthracene Photodimerization. J. Am. Chem. Soc. 1977, 99 (3), 884-896. 38. Borsarelli, C. D.; Cosa, J. J.; Previtali, C. M., Exciplex Formation Between Pyrene Derivatives and N,N-dimethylaniline in Aerosol OT Reversed Micelles. Langmuir 1992, 8 (4), 1070-1075. 39. Chandross, E. A.; Thomas, H. T., The Interaction of Amine-Hydrocarbon Exciplexes with Small Dipolar Molecules-Stoichiometric Complex Formation. Chem. Phys. Lett. 1971, 9 (5), 397-400. 40. Beens, H.; Weller, A., Triple Complex Formation in the Excited State. Chem. Phys. Lett. 1968, 2 (3), 140-142. 41. Lin, C. J.; Liu, Y. H.; Peng, S. M.; Shinmyozu, T.; Yang, J. S., Excimer-Monomer Photoluminescence Mechanochromism and Vapochromism of Pentiptycene-Containing Cyclometalated Platinum(II) Complexes. Inorg. Chem. 2017, 56 (9), 4978-4989. 42. Matsunaga, Y.; Yang, J. S., Multicolor Fluorescence Writing Based on Host-Guest Interactions and Force-Induced Fluorescence-Color Memory. Angew. Chem. Int. Ed. Engl. 2015, 54 (27), 7985-7989. 43. Yang, J. S.; Yan, J. L.; Hwang, C. Y.; Chiou, S. Y.; Liau, K. L.; Gavin Tsai, H. H.; Lee, G. H.; Peng, S. M., Probing the Intrachain and Interchain Effects on the Fluorescence Behavior of Pentiptycene-Derived Oligo(p-phenyleneethynylene)s. J. Am. Chem. Soc. 2006, 128 (43), 14109-14119. 44. Kim, Y.; Zhu, Z.; Swager, T. M., Hyperconjugative and Inductive Perturbations in Poly(p-phenylene vinylenes). J. Am. Chem. Soc. 2004, 126 (2), 452-453. | |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/72033 | - |
| dc.description.abstract | 有機分子的螢光性質可受許多外界刺激調控，如熱致螢光變色 (Thermofluorochromism, TFC)、力致螢光變色 (mechanofluorochromism, MFC) 與薰致螢光變色 (vapofluorochromism, VFC)，這些特性讓有機分子具有成為溫度、壓力與有機蒸氣之螢光偵測材料之潛力。本實驗室曾發表由蒽發光團接上兩個五苯荑基團之9,10-An-C8分子，其具有MFC與VFC性質，來自於固態下之放光行為會因為受力研磨與否而由分子單體或激發雙體主導，或者在苯胺蒸氣下會與苯胺分子形成激發錯體進行放光。這些性質與分子在固態中之排列方式有高度相關，而在分子上修飾長短不同之烷基碳鏈，能影響分子在固態下之排列情形，於是本研究中改變9,10-An-Cn (n = 4,8,12,16) 之鏈長，探討鏈長效應對於MFC與VFC之影響。此外，為了增強發光團π-π作用力或促使發光團更易形成激發雙體，我們將中間發光團換成芘，設計一系列1,6-Py-Cn (n = 4,8,12,16) 分子，探討中間發光團之大小與鏈長效應之交互關係。本研究經由歸納分子MFC、VFC性質隨鏈長變化之趨勢，整理出一個理論模型來解釋此類固態分子螢光行為中之鏈長效應，期望能應用於有機螢光偵測材料之分子設計。 | zh_TW |
| dc.description.abstract | Stimuli-responsive fluorescence properties, such as thermofluorochromism (TFC), mechanofluorochromism (MFC) and vapofluorochromism (VFC), of organic molecules are attractive because of their potential application as fluorescent sensors toward temperature, pressure, and organic vapors. A pentiptycene-derived π-conjugated molecule 9,10-An-C8, which is composed of an anthracene group and two pentiptycene moieties, has been previously reported to exhibit MFC and VFC properties in its solid state. The MFC behavior of 9,10-An-C8 was induced by excimer/monomer transformation, while the VFC behavior resulted from the exciplex formation between aniline vapor and 9,10-An-C8. Both the MFC and VFC properties are highly associated with the molelcular packing in the solid state, which might be modified by alkyl chains of different lengths. In this work, we change the alkyl chain length of 9,10-An-Cn (n = 4, 8, 12, 16) to investigate the chain length effect on the MFC and VFC properties. This is also extended to the pyrene-based analogs, 1,6-Py-Cn (n = 4, 8, 12, 16) . A model is proposed to explain the observed chain-length effects. Our results would pave the way for rational design of novel organic materials for stimuli-responsive fluorescence properties. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-17T06:20:03Z (GMT). No. of bitstreams: 1 ntu-107-R05223146-1.pdf: 19139495 bytes, checksum: ceb9ad90491c2a3fa98a004fb18befcc (MD5) Previous issue date: 2018 | en |
| dc.description.tableofcontents | 中文摘要 i
Abstract ii 目錄 iii 圖目錄 vii 表目錄 xvii 附圖目錄 xviii 第一章 前言 1 1-1碳鏈簡介 1 1-1-1碳鏈之角色 1 1-1-2碳鏈如何影響固態分子之排列 6 1-2外部刺激誘導變色 18 1-2-1熱致變色 18 1-2-2力致變色 23 1-2-3薰致變色 27 1-3蒽與芘之激發雙體與激發複合體 29 1-3-1蒽與芘之簡介 29 1-3-2激發雙體與激發複合體 30 1-4激發三重複合體 33 1-5五苯荑基團於固態放光之研究 34 1-6研究動機 38 第二章 結果與討論 40 2-1目標物之合成 40 2-1-1目標物逆合成分析 40 2-1-2目標物合成結果 41 2-2目標物於溶劑中之光物理性質 44 2-2-1 9,10-An-Cn於二氯甲烷中之光物理探討 44 2-2-2 1,6-Py-Cn於二氯甲烷中之光物理探討 46 2-3目標物之力致螢光變色探討 48 2-3-1 9,10-An-Cn之力致螢光變色探討 48 2-3-2 1,6-Py-Cn之力致螢光變色探討 55 2-4目標物之薰致螢光變色探討 61 2-4-1 9,10-An-Cn之薰致螢光變色探討 62 2-4-2 1,6-Py-Cn之薰致螢光變色探討 77 2-4-3 目標物與pMDMA於溶劑中形成激發複合體之探討 94 2-5目標物之粉末X-光繞射分析 103 2-5-1 9,10-An-Cn之X-光繞射分析 103 2-5-2 1,6-Py-Cn之X-光繞射分析 108 2-5-3 1,4-Na-Cn之X-光繞射分析 113 2-6目標物SEM影像圖 116 2-7目標物熱穩定與熱致螢光變色探討 119 2-7-1目標物熱穩定分析 119 2-7-2目標物熱致螢光變色探討 123 2-8目標物26之薰致螢光變色探討 125 第三章 提出分子排列模型 131 第四章 結論 139 第五章 實驗部分 140 5-1實驗藥品與溶劑 140 5-2-1 核磁共振光譜儀 (Nuclear Magnetic Resonance) 143 5-2-2高解析度質譜儀 (High Resolution Mass) 143 5-2-3 紅外線吸收光譜儀 (FT-Infrared Spectrometer) 144 5-2-4 熔點測定儀 (Melting Point Apparatus) 144 5-2-5 溶劑純化系統 145 5-2-6 紫外光/可見光吸收光譜儀 (Ultraviolet/Visible Spectrophotometer) 145 5-2-7 螢光光譜儀 (Fluorescence Spectrometer) 145 5-2-8 掃描式電子顯微鏡 148 5-2-9 X-光粉末繞射儀 148 5-2-10熱重分析儀 149 5-2-11低溫示差掃描量熱儀 (LT-DSC) 149 5-3實驗樣品製備方法 150 5-3-1製備UG-form薄膜之方法 150 5-3-2製備G-form薄膜之方法 150 5-3-3薰陶苯胺分子之方法 150 5-3-4薰陶二氯甲烷使目標物再結晶之方法 151 5-3-5熱致螢光變色之實驗方法 151 5-3-6測量X-光粉末繞射圖譜之樣品製備方法 151 5-3-7測量SEM影像之樣品製備方法 152 5-3-8測量TGA之樣品製備方法 152 5-3-9測量DSC之樣品製備方法 152 5-4合成步驟 153 參考資料 169 附圖 175 | |
| dc.language.iso | zh-TW | |
| dc.title | 五苯荑衍生之π共軛系統之烷基鏈長效應對蒸氣誘導螢光變色行為之探究 | zh_TW |
| dc.title | Alkyl Chain Length Effects on the Vapochromic Fluorescence Properties of Pentiptycene Derived π-Conjugated Systems | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 106-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 蔡蘊明(Yeun-Min Tsai),梁文傑(MAN-KIT LEUNG) | |
| dc.subject.keyword | 烷基鏈長效應,力致螢光變色,薰致螢光變色,熱致螢光變色,激發雙體,激發複合體,激發三重複合體, | zh_TW |
| dc.subject.keyword | alkyl chain length effect,mechanofluorochromsim,vapofluorochromsim,thermofluorochromsim,excimer,exciplex,triplex, | en |
| dc.relation.page | 231 | |
| dc.identifier.doi | 10.6342/NTU201803985 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2018-08-20 | |
| 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-107-1.pdf 目前未授權公開取用 | 18.69 MB | Adobe PDF |
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。