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研究生： 陳怡雯
Chen, Yi-Wen
論文名稱： 包含9,10-dithienylanthracene的環狀共軛分子的合成和特徵
Synthesis and characterization of cyclic conjugated molecules comprising 9,10-dithienylanthracene
指導教授： 堀江正樹
Horie, Masaki
口試委員: 周鶴修
Chou, Ho-Hsiu
游進陽
Yu, Chin-Yang
學位類別： 碩士
Master
系所名稱： 工學院 - 化學工程學系
Department of Chemical Engineering
論文出版年： 2019
畢業學年度： 107
語文別： 中文
論文頁數： 91
中文關鍵詞： 蒽噻吩衍生物 、構型異構物 、環二聚體 、光二聚化
外文關鍵詞： anthracene-containing conjugated molecules, conformer, cyclic dimer, photodimerization
相關次數： 點閱：82  下載：0 
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    • 本論文描述了含蒽共軛分子的合成，特徵和光譜性質。 我們已經通過Suzuki偶聯，Vilsmeier-Haack反應和Mcmurry反應合成了蒽單體和用二噻吩官能基的二聚體。 通過NMR和質譜表徵這些化合物。 此外，通過單晶X射線晶體學觀察蒽醛衍生物單體，產物（5）和（5）'的分子結構、由於單體中的側鏈，單體呈現出彼此不同的構型和晶體排列，通過空間效應形成結構屏障。 側鏈甚至影響環狀二聚體Ma的合成。 環狀二聚體可以僅獲得產物（5）'作為前體。 然後，使用紫外 - 可見吸收分光光度計和螢光分光光度計測量光化學性質。 Ma的光二聚化度（PD）估計為84％

    This thesis describes synthesis, characterization, and spectroscopic properties of anthracene-containing conjugated molecules. We have synthesized anthracene monomers and dimer tethered with two thiophenes by Suzuki coupling, Vilsmeier-Haack reaction, and Mcmurry reaction. These compounds were characterized by NMR and field desorption mass spectroscopies. In addition, molecular structures of aldehyde derivative monomers, product (5) and (5)’, were observed by single-crystal X-ray crystallography. The monomers presented different conformation and crystal arrangement to each other due to the side chains in the monomers, forming the structure barrier by steric effect. The side chains even affect the synthesis of cyclic dimer Ma. Cyclic dimer can be obtained only product (5)’ as precursor. Then, the photochemical properties were measured using UV-vis absorption spectrophotometer and fluorescence Spectrophotometer. The photodimerization degree (PD) of Ma was estimated to be 84%

    Abstract I Chapter 1 Introduction 1 1-1 Introduction to conjugated polymers 1 1-1-1 Conjugated polymers 1 1-1-2 Organic photovoltaics based on conjugated polymers 1 1-1-3 Organic field-effect transistors based on conjugated polymers 9 1-2 Introduction to synthesis methods 14 1-2-1 Olefin metathesis 14 1-2-2 Mechanism of ROMP 15 1-2-3 Catalysts for living polymerization ROMP 17 1-2-4 A donor-acceptor conjugated block copolymer of poly(arylenevinylene)s through ROMP 19 1-3 Introduction to anthracene 21 1-3-1 Basic properties of anthracene 21 1-3-2 [4 + 4] Photodimerization of anthracene derivatives 23 1-3-3 Advanced anthracene-containing polymers 33 1-4 Aim of work 39 Chapter 2 Synthesis of dithienyl-anthracene compounds 41 2-1 Synthesis of monomers 41 2-1-1 Synthesis of 9,10-bis(3-hexylthiophen-2-yl)anthracene Ma and Mb 42 2-1-2 X-ray crystallography of 5,5'-(anthracene-9,10-diyl)bis(4-hexylthiophene-2-carbaldehyde) (5) and (5)’ 52 2-1-3 Analysis of 9,10-bis(3-hexylthiophen-2-yl)anthracene Ma and Mb 56 2-2 Optical properties of small molecules in solution 62 2-2-1 Photochemical reaction in solution 62 2.2-2 UV-vis absorption spectra 62 2.2-3 Fluorescence emission spectra 65 Chapter 3 Conclusion 67 Chapter 4 Future work 68 Chapter 5 Experiment section 69 5-1 General methods 69 5-2 Synthesis of monomer 69 5-2-1 Synthesis of 9,10-bis(3-hexylthiophen-2-yl)anthracene M 69 5-2-1-1 Synthesis of 3-hexylthiophene (1) 69 5-2-1-2 Synthesis of 2-bromo-3-hexylthiophene (2) 70 5-2-1-3 Synthesis of 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3) 70 5-2-1-4 Synthesis of 9,10-bis(3-hexylthiophen-2-yl)anthracene (4) (4)’ 71 5-2-1-5 Synthesis of 5,5'-(anthracene-9,10-diyl)bis(4-hexylthiophene-2-carbaldehyde) (5) and (5)’ 72 5-2-1-6 Synthesis of 9,10-bis(3-hexylthiophen-2-yl)anthracene Ma, Mb 74 5-3 Synthesis of oligomer O1 75 References 88

    1. Winder, C.; Sariciftci, N. S., J. Mater. Chem. 2004, 14 (7), 1077-1086
    2. Tang, C. W., Appl. Phys. Lett. 1986, 48 (2), 183-185
    3. Kraabel, B.; Lee, C. H.; McBranch, D.; Moses, D.; Sariciftci, N. S.; Heeger, A. J., Chem. Phys. Lett. 1993, 213 (3-4), 389-394
    4. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J., Science 1995, 270 (5243), 1789-1791
    5. Chao, Y.-H.; Jheng, J.-F.; Wu, J.-S.; Wu, K.-Y.; Peng, H.-H.; Tsai, M.-C.; Wang, C.-L.; Hsiao, Y.-N.; Wang, C.-L.; Lin, C.-Y.; Hsu, C.-S., Adv. Mater. 2014, 26 (30), 5205-5210
    6. Gao, L.; Zhang, Z.-G.; Xue, L.; Min, J.; Zhang, J.; Wei, Z.; Li, Y., Adv. Mater. 2016, 28 (9), 1884-1890
    7. Zhao, W.; Li, S.; Zhang, S.; Liu, X.; Hou, J., Adv. Mater. 2017, 29 (2), 1604059
    8. Kim, J.-H.; Park, J. B.; Xu, F.; Kim, D.; Kwak, J.; Grimsdale, A. C.; Hwang, D.-H., Science 2014, 7 (12), 4118-4131
    9. Zhang, T.; Feng, W.; Wang, W.; Zhen, H.; Chen, P.; Ling, Q., J. Mater. Chem. C 2018, 6 (31), 8418-8428
    10. Lilienfeld, J. JE Lilienfeld US Patent, 1 (1930). US patent 1930, 1, 175.
    11. Arias, A. C.; MacKenzie, J. D.; McCulloch, I.; Rivnay, J.; Salleo, A., Chem. Rev. 2010, 110 (1), 3-24.
    12. Fukuda, K.; Takeda, Y.; Yoshimura, Y.; Shiwaku, R.; Tran, L. T.; Sekine, T.; Mizukami, M.; Kumaki, D.; Tokito, S., Nat. Commun. 2014, 5, 4147.
    13. Guo, X.; Xu, Y.; Ogier, S.; Ng, T. N.; Caironi, M.; Perinot, A.; Li, L.; Zhao, J.; Tang, W.; Sporea, R. A., IEEE Trans. Electron Devices 2017, 64 (5), 1906-1921.
    14. Gundlach, D. J., Nat. Mater. 2007, 6 (3), 173.
    15. Quinn, J. T.; Zhu, J.; Li, X.; Wang, J.; Li, Y., J. Mater. Chem. C 2017, 5 (34), 8654-8681.
    16. Lakshminarayana, A. N.; Ong, A.; Chi, C., J. Mater. Chem. C 2018, 6 (14), 3551-3563.
    17. Hasegawa, T.; Takeya, J., Sci. Technol. Adv. Mater. 2009, 10 (2), 024314.
    18. Lei, T.; Dou, J. H.; Pei, J., Adv. Mater. 2012, 24 (48), 6457-6461
    19. Kanimozhi, C.; Yaacobi-Gross, N.; Chou, K. W.; Amassian, A.; Anthopoulos, T. D.; Patil, S., J. Am. Chem. Soc. 2012, 134 (40), 16532-16535
    20. Kang, I.; Yun, H.-J.; Chung, D. S.; Kwon, S.-K.; Kim, Y.-H., J. Am. Chem. Soc. 2013, 135 (40), 14896-14899
    21. Zhao, Y.; Zhao, X.; Roders, M.; Qu, G.; Diao, Y.; Ayzner, A. L.; Mei, J., Chem. Mater. 2015, 27 (20), 7164-7170
    22. Rivnay, J.; Jimison, L. H.; Northrup, J. E.; Toney, M. F.; Noriega, R.; Lu, S.; Marks, T. J.; Facchetti, A.; Salleo, A., Nat. Mater. 2009, 8 (12), 952.
    23. Tseng, H. R.; Phan, H.; Luo, C.; Wang, M.; Perez, L. A.; Patel, S. N.; Ying, L.; Kramer, E. J.; Nguyen, T. Q.; Bazan, G. C., Adv. Mater. 2014, 26 (19), 2993-2998.
    24. Grubbs, R. H.; Chang, S., Tetrahedron 1998, 54 (18), 4413-4450
    25. Schrock, R. R.; Hoveyda, A. H., Angew. Chem., Int. Ed. 2003, 42 (38), 4592-4633
    26. Trnka, T. M.; Grubbs, R. H., Acc. Chem. Res. 2001, 34 (1), 18-29
    27. Bielawski, C. W.; Grubbs, R. H., Prog. Polym. Sci. 2007, 32 (1), 1-29
    28. Chauvin, Y., Angew. Chem., Int. Ed. 2006, 45 (23), 3740-3747
    29. Bielawski, C. W.; Grubbs, R. H., Prog. Polym. Sci. 2007, 32 (1), 1-29
    30. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W., J. Am. Chem. Soc. 1992, 114 (10), 3974-3975
    31. Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W., J. Am. Chem. Soc. 1993, 115 (21), 9858-9859
    32. Schwab, P.; Grubbs, R. H.; Ziller, J. W., J. Am. Chem. Soc. 1996, 118 (1), 100-110
    33. Yu, C.-Y.; Wen, S.-H.; Yu, S.-H.; Wang, C.-C., J. Polym. Sci., Part A: Polym. Chem. 2018, 56 (1), 67-74
    34. Chen, B.; Sleiman, H. F., Macromolecules 2004, 37 (16), 5866-5872
    35. Nomura, K.; Abdellatif, M. M., Polymer 2010, 51 (9), 1861-1881
    36. Elacqua, E.; Weck, M., Chem. Eur. J. 2015, 21 (19), 7151-7158
    37. Chang, S.-W.; Horie, M., Chem. Commun. 2015, 51 (44), 9113-9116
    38. Van Damme, J.; Du Prez, F., Prog. Polym. Sci. 2018, 82, 92-119
    39. Schuster, P.; Brubaker, E., IEEE Trans. Nucl. Sci. 2016, 63 (3), 1942-1954
    40. Szemenyei, B.; Moczar, I.; Pal, D.; Kocsis, I.; Baranyai, P.; Huszthy, P., Chirality 2016, 28 (7), 562-568
    41. Conoci, S.; Mascali, A.; Pappalardo, F., RSC Adv. 2014, 4 (6), 2845-2850
    42. Lee, H. G.; Kim, K. B.; Park, G. J.; Na, Y. J.; Jo, H. Y.; Lee, S. A.; Kim, C., Inorg. Chem. Commun. 2014, 39, 61-65
    43. Kaur, N.; Dhaka, G.; Singh, J., New J. Chem. 2015, 39 (8), 6125-6129
    44. Almeataq, M. S.; Yi, H.; Al-Faifi, S.; Alghamdi, A. A.; Iraqi, A.; Scarratt, N. W.; Wang, T.; Lidzey, D. G., Chem. Commun. (Camb.) 2013, 49 (22), 2252-4
    45. Liu, C.; Cai, W.; Guan, X.; Duan, C.; Xue, Q.; Ying, L.; Huang, F.; Cao, Y., Polym. Chem. 2013, 4 (14), 3949
    46. Back, J. Y.; An, T. K.; Cheon, Y. R.; Cha, H.; Jang, J.; Kim, Y.; Baek, Y.; Chung, D. S.; Kwon, S.-K.; Park, C. E.; Kim, Y.-H., ACS Appl. Mater. Interfaces 2015, 7 (1), 351-358
    47. Meng, H.; Sun, F.; Goldfinger, M. B.; Jaycox, G. D.; Li, Z.; Marshall, W. J.; Blackman, G. S., J. Am. Chem. Soc. 2005, 127 (8), 2406-2407
    48. Fritzsche, J., J. prakt. Chem. 1866, 97 (1), 290-303
    49. Van Damme, J.; Vlaminck, L.; Van Assche, G.; Van Mele, B.; van den Berg, O.; Du Prez, F., Tetrahedron 2016, 72 (29), 4303-4311
    50. Bringmann, S.; Brodbeck, R.; Hartmann, R.; Schafer, C.; Mattay, J., Org. Biomol. Chem. 2011, 9 (21), 7491-7499
    51. Spinelli, F.; d'Agostino, S.; Taddei, P.; Jones, C. D.; Steed, J. W.; Grepioni, F., Dalton Trans. 2018, 47 (16), 5725-5733
    52. Tamaki, T.; Kokubu, T.; Ichimura, K., Tetrahedron 1987, 43 (7), 1485-1494
    53. Schmidt, G. M. J., J. Chem. Soc. 1964, (0), 2014-2021
    54. Schmidt, G. M. J., Pure Appl. Chem. 1971, 27 (4), 647-678.
    55. Yamada, S.; Uematsu, N.; Yamashita, K., J. Am. Chem. Soc. 2007, 129 (40), 12100-12101
    56. Constable, E. C.; Zhang, G.; Housecroft, C. E.; Zampese, J., Dalton Trans. 2011, 40 (45), 12146-12152
    57. Tung, C.-H.; Wu, L.-Z.; Yuan, Z.-Y.; Su, N., J. Am. Chem. Soc. 1998, 120 (45), 11594-11602
    58. Yamada, S.; Kawamura, C., Org. Lett. 2012, 14 (6), 1572-1575
    59. Wang, R.; Liu, H.; Li, J.; Tian, J.; Li, Z.; Zhao, Y. ASIAN J. ORG. CHEM. Journal 2018, 7 (5), 906-909
    60. Marquis, D.; Desvergne, J.-P.; Bouas-Laurent, H., J. Org. Chem. 1995, 60 (24), 7984-7996
    61. Spinelli, F.; d'Agostino, S.; Taddei, P.; Jones, C. D.; Steed, J. W.; Grepioni, F. Dalton Trans. 2018, 47 (16), 5725-5733
    62. Gui, J.-C.; Yan, Z.-Q.; Peng, Y.; Yi, J.-G.; Zhou, D.-Y.; Su, D.; Zhong, Z.-H.; Gao, G.-W.; Wu, W.-H.; Yang, C., Chin. Chem. Lett. 2016, 27 (7), 1017-1021
    63. Tanabe, J.; Taura, D.; Ousaka, N.; Yashima, E., J. Am. Chem. Soc. 2017, 139 (21), 7388-7398
    64. Liu, Y.; Chang, H.; Jiang, J.; Yan, X.; Liu, Z.; Liu, Z. RSC Adv. 2014, 4 (49), 25912-25915
    65. Rahaman, S. A.; Hossain, M. S.; Baburaj, S.; Biswas, A.; Bag, A. Org. Biomol. Chem. 2019, 17 (20), 5153-5160
    66. Ali, A.; Bullen, G. A.; Cross, B.; Dafforn, T. R.; Little, H. A.; Manchester, J.; Peacock, A. F. A.; Tucker, J. H. R. 2019, 55 (39), 5627-5630
    67. Banerjee, A.; Sahana, A.; Lohar, S.; Sarkar, B.; Mukhopadhyay, S. K.; Das, D., RSC Adv. 2013, 3 (34), 14397-14405
    68. Dadvand, A.; Sun, W.-H.; Moiseev, A. G.; Bélanger-Gariépy, F.; Rosei, F.; Meng, H.; Perepichka, D. F., J. Mater. Chem. C 2013, 1 (16), 2817-2825
    69. Almeataq, M. S.; Yi, H.; Al-Faifi, S.; Alghamdi, A. A. B.; Iraqi, A.; Scarratt, N. W.; Wang, T.; Lidzey, D. G., Chem. Commun. 2013, 49 (22), 2252-2254
    70. Jung, J. W.; Liu, F.; Russell, T. P.; Jo, W. H., Adv. Energy Mater. 2015, 5 (11), 1500065
    71. Yu, B.; Zhao, Y., Polym. Chem. 2017, 8 (28), 4132-4139
    72. Tao, Y.; Zhang, K.; Zhang, Z.; Cheng, H.; Jiao, C.; Zhao, Y., Chem. Eng. J. 2016, 293, 34-43
    73. Grigoras, M.; Sava, M.; Colotin, G.; Simionescu, C. I., J. Appl. Polym. Sci. 2008, 107 (2), 846-853
    74. Biedermann, F.; Ross, I.; Scherman, O., Polym. Chem. 2014, 5 (18), 5375-5382
    75. Durmaz, H.; Hizal, G.; Tunca, U., J Polym. Sci. A Polym. Chem. 2011, 49 (9), 1962-1968
    76. Wang, H.; Zhang, L.; Liu, B.; Han, B.; Duan, Z.; Qi, C.; Park, D.-W.; Kim, I., Macromol. Rapid Commun. 2015, 36 (18), 1646-1650
    77. López-Vilanova, L.; Martínez, I.; Corrales, T.; Catalina, F., Eur. Polym. J. 2014, 56, 69-76
    78. Manhart, J.; Ayalur-Karunakaran, S.; Radl, S.; Oesterreicher, A.; Moser, A.; Ganser, C.; Teichert, C.; Pinter, G.; Kern, W.; Griesser, T.; Schlögl, S., Polymer 2016, 102, 10-20
    79. Sun, H.; Kabb, C. P.; Dai, Y.; Hill, M. R.; Ghiviriga, I.; Bapat, A. P.; Sumerlin, B. S., Nat. Chem. 2017, 9, 817

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