請用此 Handle URI 來引用此文件:
http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/67505
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 | Chiao-Min Cheng | en |
dc.contributor.author | 鄭巧旻 | zh_TW |
dc.date.accessioned | 2021-06-17T01:35:10Z | - |
dc.date.available | 2025-08-24 | |
dc.date.copyright | 2020-09-16 | |
dc.date.issued | 2020 | |
dc.date.submitted | 2020-08-25 | |
dc.identifier.citation | 1. Wang, Z.; Zhu, M.; Gou, S.; Pang, Z.; Wang, Y.; Su, Y.; Huang, Y.; Weng, Q.; Schmidt, O. G.; Xu, J., Pairing of Luminescent Switch with Electrochromism for Quasi-Solid-State Dual-Function Smart Windows. ACS Appl. Mater. Interfaces 2018, 10, 31697-31703. 2. Hai, J.; Wang, H.; Sun, P.; Li, T.; Lu, S.; Zhao, Y.; Wang, B., Smart Responsive Luminescent Aptamer-Functionalized Covalent Organic Framework Hydrogel for High-Resolution Visualization and Security Protection of Latent Fingerprints. ACS Appl. Mater. Interfaces 2019, 11, 44664-44672. 3. 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, 3018-3027. 4. Wang, C.; Yu, Y.; Yuan, Y.; Ren, C.; Liao, Q.; Wang, J.; Chai, Z.; Li, Q.; Li, Z., Heartbeat-Sensing Mechanoluminescent Device Based on a Quantitative Relationship between Pressure and Emissive Intensity. Matter 2020, 2, 181-193. 5. Seki, T.; Ozaki, T.; Okura, T.; Asakura, K.; Sakon, A.; Uekusa, H.; Ito, H., Interconvertible multiple photoluminescence color of a gold(i) isocyanide complex in the solid state: solvent-induced blue-shifted and mechano-responsive red-shifted photoluminescence. Chem. Sci. 2015, 6, 2187-2195. 6. Esser, B.; Swager, T. M., Detection of ethylene gas by fluorescence turn-on of a conjugated polymer. Angew. Chem. Int. Ed. Engl. 2010, 49, 8872-8875. 7. Wu, Y.; Wang, J.; Zeng, F.; Huang, S.; Huang, J.; Xie, H.; Yu, C.; Wu, S., Pyrene Derivative Emitting Red or near-Infrared Light with Monomer/Excimer Conversion and Its Application to Ratiometric Detection of Hypochlorite. ACS Appl. Mater. Interfaces 2016, 8, 1511-1519. 8. Lakowicz, J. R., Principles of fluorescence spectroscopy. Springer science business media: 2013. 9. Liu, H.; Yao, L.; Li, B.; Chen, X.; Gao, Y.; Zhang, S.; Li, W.; Lu, P.; Yang, B.; Ma, Y., Excimer-induced high-efficiency fluorescence due to pairwise anthracene stacking in a crystal with long lifetime. Chem. Commun. 2016, 52, 7356-7359. 10. Hirota, J.; Usui, K.; Fuchi, Y.; Sakuma, M.; Matsumoto, S.; Hagihara, R.; Karasawa, S., Fluorescence Properties and Exciplex Formation of Emissive Naphthyridine Derivatives: Application as Sensors for Amines. Chem. Eur. J. 2019, 25, 14943-14952. 11. Huang, B.; Chen, W. C.; Li, Z.; Zhang, J.; Zhao, W.; Feng, Y.; Tang, B. Z.; Lee, C. S., Manipulation of Molecular Aggregation States to Realize Polymorphism, AIE, MCL, and TADF in a Single Molecule. Angew. Chem. Int. Ed. Engl. 2018, 57, 12473-12477. 12. Li, W.; Huang, Q.; Mao, Z.; Zhao, J.; Wu, H.; Chen, J.; Yang, Z.; Li, Y.; Yang, Z.; Zhang, Y.; Aldred, M. P.; Chi, Z., Selective Expression of Chromophores in a Single Molecule: Soft Organic Crystals Exhibiting Full-Colour Tunability and Dynamic Triplet-Exciton Behaviours. Angew. Chem. Int. Ed. 2020, 59, 3739-3745. 13. Houjou, H.; Kato, T.; Huang, H.; Suzuki, Y.; Yoshikawa, I.; Mutai, T., Re-evaluation of the tert-Butyl Method in Crystal Engineering of Salicylideneanilines by Simultaneous Observation of Photochromism and Thermochromism in Single Crystals. Cryst. Growth Des. 2019, 19, 1384-1390. 14. Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S., Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators. Chem. Rev. 2014, 114, 12174-12277. 15. Liu, G.; Zhang, Y.-M.; Zhang, L.; Wang, C.; Liu, Y., Controlled Photoerasable Fluorescent Behaviors with Dithienylethene-Based Molecular Turnstile. ACS Appl. Mater. Interfaces 2018, 10, 12135-12140. 16. Chung, J. W.; You, Y.; Huh, H. S.; An, B.-K.; Yoon, S.-J.; Kim, S. H.; Lee, S. W.; Park, S. Y., Shear- and UV-Induced Fluorescence Switching in Stilbenic π-Dimer Crystals Powered by Reversible [2 + 2] Cycloaddition. J. Am. Chem. Soc. 2009, 131, 8163-8172. 17. Zhu, L.; Tong, F.; Salinas, C.; Al-Muhanna, M. K.; Tham, F. S.; Kisailus, D.; Al-Kaysi, R. O.; Bardeen, C. J., Improved Solid-State Photomechanical Materials by Fluorine Substitution of 9-Anthracene Carboxylic Acid. Chem. Mater. 2014, 26, 6007-6015. 18. Biradha, K.; Santra, R., Crystal engineering of topochemical solid state reactions. Chem. Soc. Rev. 2013, 42, 950-967. 19. Nagura, K.; Saito, S.; Yusa, H.; Yamawaki, H.; Fujihisa, H.; Sato, H.; Shimoikeda, Y.; Yamaguchi, S., Distinct responses to mechanical grinding and hydrostatic pressure in luminescent chromism of tetrathiazolylthiophene. J. Am. Chem. Soc. 2013, 135, 10322-10325. 20. 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. 21. Wang, K.; Huang, S.; Zhang, Y.; Zhao, S.; Zhang, H.; Wang, Y., Multicolor fluorescence and electroluminescence of an ICT-type organic solid tuned by modulating the accepting nature of the central core. Chem. Sci. 2013, 4, 3288-3293. 22. Li, Q.; Zhu, H.; Huang, F., Alkyl Chain Length-Selective Vapor-Induced Fluorochromism of Pillar[5]arene-Based Nonporous Adaptive Crystals. J. Am. Chem. Soc. 2019, 141, 13290-13294. 23. Mu, B.; Zhao, Y.; Li, X.; Quan, X.; Tian, W., Enhanced Conductivity and Thermochromic Luminescence in Hydrogen Bond-Stabilized Columnar Liquid Crystals. ACS Appl. Mater. Interfaces 2020, 12, 9637-9645. 24. Kaneko, R.; Sagara, Y.; Katao, S.; Tamaoki, N.; Weder, C.; Nakano, H., Mechano- and Photoresponsive Behavior of a Bis(cyanostyryl)benzene Fluorophore. Chem. Eur. J. 2019, 25, 6162-6169. 25. Peng, J.; Ye, K.; Liu, C.; Sun, J.; Lu, R., The photomechanic effects of the molecular crystals based on 5-chloro-2-(naphthalenylvinyl)benzoxazols fueled by topo-photochemical reactions. J. Mater. Chem. C 2019, 7, 5433-5441. 26. Hart, H.; Bashir-Hashemi, A.; Luo, J.; Meador, M. A., Iptycenes: Extended triptycenes. Tetrahedron 1986, 42, 1641-1654. 27. Yang, J.-S.; Huang, Y.-T.; Ho, J.-H.; Sun, W.-T.; Huang, H.-H.; Lin, Y.-C.; Huang, S.-J.; Huang, S.-L.; Lu, H.-F.; Chao, I., A Pentiptycene-Derived Light-Driven Molecular Brake. Org. Lett. 2008, 10, 2279-2282. 28. Tan, W. S.; Lee, T. Y.; Hsu, Y. F.; Huang, S. J.; Yang, J. S., Iptycene substitution enhances the electrochemical activity and stability of polyanilines. Chem. Commun. 2018, 54, 5470-5473. 29. Yang, J.-S.; Liu, C.-P.; Lee, G.-H., Anomalous crystal packing of iptycene secondary diamides leading to novel chain and channel networks. Tetrahedron Lett. 2000, 41, 7911-7915. 30. 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, 4978-4989. 31. Matsunaga, Y.; Yang, J.-S., Multicolor Fluorescence Writing Based on Host–Guest Interactions and Force-Induced Fluorescence-Color Memory. Angew. Chem. Int. Ed. 2015, 54, 7985-7989. 32. Hsu, L. Y.; Maity, S.; Matsunaga, Y.; Hsu, Y. F.; Liu, Y. H.; Peng, S. M.; Shinmyozu, T.; Yang, J. S., Photomechanochromic vs. mechanochromic fluorescence of a unichromophoric bimodal molecular solid: multicolour fluorescence patterning. Chem. Sci. 2018, 9, 8990-9001. 33. Kuo, C.-Z.; Hsu, L.-Y.; Chen, Y.-S.; Goto, K.; Maity, S.; Liu, Y.-H.; Peng, S.-M.; Kang, K. V.; Shinmyozu, T.; Yang, J.-S., Alkyl Chain Length- and Polymorph-Dependent photomechanochromic fluorescence of anthracene photodimerization in molecular crystals: roles of the lattice stiffness. Chem. Eur. J. 2020, DOI: 10.1002/chem.202000353. 34. Lohr, A.; Swager, T. M., Stabilization of the nematic mesophase by a homogeneously dissolved conjugated polymer. J. Mater. Chem. 2010, 20, 8107-8111. 35. Yanus, J. F.; Stolka, M.; Pearson, J. M., Polymerization of Vinylanthracene Monomers. 4. A Spectroscopic Study of the Anionic Polymerization of 1-, 2-, and 9-Vinylanthracenes. Macromolecules 1976, 9, 719-723. 36. Yang, J.-S.; Ko, C.-W., Pentiptycene Chemistry: New Pentiptycene Building Blocks Derived from Pentiptycene Quinones. J. Org. Chem. 2006, 71, 844-847. 37. Arai, T.; Tokumaru, K., Photochemical one-way adiabatic isomerization of aromatic olefins. Chem. Rev. 1993, 93, 23-39. 38. Yang, J.-S.; Swager, T. M., Fluorescent Porous Polymer Films as TNT Chemosensors: Electronic and Structural Effects. J. Am. Chem. Soc. 1998, 120, 11864-11873. | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/67505 | - |
dc.description.abstract | 近年來,刺激響應材料受到科學家的關注,因為其具有多樣化的應用潛力如感應器、光學記憶材料及加密/解密材料等等。常見的外力如光、熱、機械力或是化學蒸氣等等。本實驗室先前所發表的文獻中,以五苯荑連接蒽的化合物1-AnPC8分子,經過光照反應形成二聚體時,有如機械力施加而改變分子的排列,影響了其螢光放光,稱為光致機械力螢光變色 (photomechanofluorochromism, PMFC),這樣特殊的光致機械力螢光變色性質為光控智能材料開啟新的篇章。 本論文試圖探討分子結構上的變化對於晶體結構的影響,以及其對光致機械力螢光變色行為的容忍程度。而分子結構的變化則藉由改變五苯荑與蒽之間的π鍵結橋樑為策略。我們成功合成了兩個目標化合物: YYP及EP。結果顯示,以參鍵延伸共軛的化合物YYP,在固態下放光顏色分布於藍色到綠色之間,顯示了延伸共軛影響到蒽與蒽之間的排列,較不利於進行 [4+4] 光二聚體反應,而減弱了光致機械力螢光變色性質。相反地,將1-AnPC8的參鍵改為雙鍵的分子EP則具有明顯的光致機械力螢光變色的性質。然而,我們發現延伸參鍵後,使得晶體有不同的堆疊外也有不同的溶劑 (客體) 參與其中,具有五種同質多形體。在YYP晶體中發現主要分為兩種堆疊模式,我們試圖分析晶體結構中的排列模式,並且嘗試置換具有電子予體性質的苯胺客體分子,利用主客作用力來調控晶體的放光顏色。 | zh_TW |
dc.description.abstract | Stimuli-responsive materials have drawn much attention recently because of their potential applications as biosensors, optical memory materials, and encryption/decryption system. The common stimuli are light, heat, mechanical force and chemical vapor. Our previous work on 1-AnPC8 showed that the fluorescence of the crystal changed as a result of the mechanical stress generated by the [4+4] photodimerization reaction, which is called photomechanofluorochromism, abbreviated as PFMC. In this work, we tried to investigate crystal packing and photomechanofluorochromisim property of the analogues of 1-AnPC8. We successfully synthesized two new derivatives YYP and EP, which are designed by changing the π-linker between the anthracene and the pentiptycene unit. Our results show that the π-linker can affect the interactions between two adjacent anthracene moieties and the topochemical reaction. On the other hand, YYP shows five polymorphs with different solvent inclusion. We also tried to place electron-donating aniline as the guest molecule to tune the luminescence of the crystal. | en |
dc.description.provenance | Made available in DSpace on 2021-06-17T01:35:10Z (GMT). No. of bitstreams: 1 U0001-1508202016550000.pdf: 16815978 bytes, checksum: afd8455dc96794418a83c47d70802831 (MD5) Previous issue date: 2020 | en |
dc.description.tableofcontents | 謝誌 I 摘要 II Abstract III 圖目錄 VI 表目錄 X 附圖目錄 XI 附錄目錄 XII 第一章 緒論 1 1-1 前言 1 1-2 固態智能放光材料之簡介 2 1-3 放光顏色的調控 2 1-3-1 激發雙體及激發複合體 2 1-3-2 同質多晶形性 (Polymorphsim) 5 1-3-3 固態光化學反應 (photochemical reaction) 6 1-3-3.1 單分子之固態光化學反應 6 1-3-3.2 雙分子之固態光化學反應 8 1-3-3.3 拓樸化學 (topochemistry) 10 1-4 外力刺激響應放光變色材料 11 1-4-1 力致放光變色 (mechanochromic luminescence) 11 1-4-2 薰致放光變色 (vapochromic luminescence) 13 1-4-3 熱致放光變色 (thermochromic luminescence) 14 1-4-4 光致放光變色 (photochromic luminescence) 15 1-5 苯荑分子 (Iptycenes) 之介紹 19 1-5-1 五苯荑蒽之螢光感應材料 21 1-5-2 五苯荑之光致機械力螢光變色 (photomechanofluorochromism) 22 1-6 研究動機 28 第二章 結果與討論 29 2-1 目標化合物的合成 29 2-1-1 目標化合物之逆合成分析 29 2-1-2 目標化合物之合成 30 2-2 目標化合物之液態光物理性質 33 2-3 目標化合物之固態光物理性質 35 2-3-1 目標化合物之同質多形體 35 2-3-2 目標化合物粉末之光物理性質 36 2-3-2.1 化合物YYP之固態粉末 36 2-3-2.2 化合物EP之固態粉末 37 2-3-3 目標化合物晶體之光物理性質 38 2-3-3.1 化合物YYP之晶體 38 2-3-3.2 化合物EP之晶體 40 2-3-3.3 鍵結橋樑對固態放光之影響 41 2-4 化合物YYP之晶體資訊分析 42 2-4-1 主導晶體堆疊的作用力 42 2-4-2 晶體堆疊之緊密程度 48 2-4-3 鍵結橋樑長度以及彎曲角度 53 2-4-4 五苯荑與蒽平面之二面角 54 2-5 與N,N-二甲基苯胺溶劑共晶結果 55 2-6 目標化合物機械力及蒸氣刺激響應 59 2-7 目標化合物之光致機械力螢光變色性質探討 62 2-7-1 目標化合物之晶體篩選 62 2-7-2 機制推測 65 2-7-2.1 化合物EP之Y型光致機械力螢光變色 65 2-7-2.2 化合物EP之G型光致螢光變色 68 2-7-3 鍵結橋樑對光致機械力螢光變色之影響 70 第三章 結論 71 第四章 實驗部分 72 4-1 實驗藥品與溶劑 72 4-2 實驗儀器 75 4-3 樣品準備以及實驗方法 78 4-4 實驗步驟 80 參考資料 90 附圖 94 附錄-化合物YEP 192 | |
dc.language.iso | zh-TW | |
dc.title | π鍵結橋樑效應對蒽-五苯荑衍生物之晶體結構及光致機械力螢光變色之探討 | zh_TW |
dc.title | Study on the Crystal Structure and Photomechanofluorochromism of Anthracene Pentiptycene Derivatives: Effects of the π-linkers | en |
dc.type | Thesis | |
dc.date.schoolyear | 108-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 孫世勝(Shih-Sheng Sun),陳志欣(Chih-Hsin Chen),張慕傑(Mu-Chieh Chang) | |
dc.subject.keyword | 蒽-五苯荑延伸物,光致機械力螢光變色,晶體結構, | zh_TW |
dc.subject.keyword | anthracene-pentiptycene derivatives,photomechanofluorochromisim,crystal strucutre, | en |
dc.relation.page | 217 | |
dc.identifier.doi | 10.6342/NTU202003528 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2020-08-26 | |
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 | |
---|---|---|---|
U0001-1508202016550000.pdf 目前未授權公開取用 | 16.42 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。