跳到主要內容

臺灣博碩士論文加值系統

(44.212.99.208) 您好!臺灣時間:2024/04/23 23:14
字體大小: 字級放大   字級縮小   預設字形  
回查詢結果 :::

詳目顯示

: 
twitterline
研究生:王則盛
研究生(外文):WANG, TSE-SHENG
論文名稱:設計合成與分析鑑定具有苯並噻唑官能基的D-π-A系統有機小分子化合物
論文名稱(外文):Design, Synthesis and Characterization of D-π-A Molecules Containing Benzothiazole Moiety.
指導教授:陳志賢陳志賢引用關係
口試委員:陳奎佑曾怡享
口試日期:2017-06-27
學位類別:碩士
校院名稱:逢甲大學
系所名稱:化學工程學系
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2017
畢業學年度:105
語文別:中文
論文頁數:78
中文關鍵詞:推拉電子基結構分子溶劑效應聚集誘導發光
外文關鍵詞:D-π-A structural compoundsSolvent effectAggregation Induced Emission
相關次數:
  • 被引用被引用:0
  • 點閱點閱:109
  • 評分評分:
  • 下載下載:1
  • 收藏至我的研究室書目清單書目收藏:0
本篇論文將參考已成功合成出具雙光子吸收特性染料的文獻,設計合成出兩種具有推拉電子基的小分子,兩化合物均由苯並噻唑基(Benzothiazole)與胺基所組成,化合物DCNB結構中有著做為電子供體的Dimethylamine與做為電子受體的Benzothiazole,化合物CCNB結構中有著做為電子供體的Carbazole與做為電子受體的Benzothiazole。
將合成出的化合物進行光學性質的測試,發現本論文合成的兩個化合物均具有聚集誘導發光的能力(Aggregation-Induced Emission, AIE),於AIE實驗中,聚集後在500nm-700nm間表現出橘黃色的螢光,並將兩個化合物進行固態螢光量子產率的測試分別得出0.119及0.063的螢光量子產率。利用電化學方法,分別測定出HOMO (Highestoccupied molecular orbital)能階與LUMO(Lowest unoccupied molecular orbital)能階於-5.36ev與-2.79ev以及-5.70ev與-3.03ev。

Recently,small molecules with D-π-A structurehave been widely used in light-emitting diodes, solar cells and two-photon absorption (TPA) dyes. Consequenly,two small molecules with D-π-A structure were designed and synthesizedin which amineand benzothiazolyl groups were chosen as donar and acceptor moieties. Photophysical and electrochemical measurements were utilized, and then, the results showed that thesetwo compounds exhibited aggregation-induced emission(AIE) ranged from 500 to 700 nm. Moreover, the fluorescence quantum yield of CCNB and DCNB was 0.12 and 0.06 in solid state, respectively.On the other hand, theenergy levels of highest occupied and lowest unoccupied molecular orbitalsfor those D-π-Amolecules were also determined.It is expected that this molecular structure might provide an useful platform for further investigation of TPA dye.
致謝 I
摘要 II
ABSTRACT III
目錄 IV
圖目錄 VI
表目錄 VI
第一章緒論 1
1.1 研究背景 1
1.2 研究動機 1
1.3 研究目的 2
第二章文獻回顧 3
2.1 具推拉電子基結構化合物 3
2.2雙光子吸收的發展與歷史 7
2.3 能進行雙光子吸收的化合物 8
2.4 雙光子染料在生物成像上的應用 15
2.5 雙光子染料在光動力療法上的應用 21
2.6 文獻總結 26
第三章實驗方法 27
3.1 實驗藥品 27
3.2 實驗步驟 28
3.3 檢測儀器 34
3.4 檢測方法 35
3.4.1 吸收光譜 35
3.4.2 螢光光譜 35
3.4.3 聚集誘導發光(Aggregation-Induced Emission) 36
3.4.4 固態量子產率 36
3.4.5循環伏安法 37
3.4.6 核磁共振儀 37
第四章結果與討論 38
4.1光化學性質 38
4.1.1 化合物的吸收及螢光光譜 38
4.1.2 溶劑效應 40
4.1.3 聚集誘導發光(Aggregation-Induced Emission) 45
4.1.4固態螢光量子產率 48
4.2 電化學性質 49
4.2.1循環伏安法 49
第五章結論 53
附錄 54
參考文獻 60

1.Goeppert-Mayer M, Über Elementarakte mit zwei quantensprüngen, Annals
of Physics, 1931, 9, 273-95.
2.A. Ishii,Y Makishima, N. Nakata,Red and near-infrared photoluminescence of
D-π-A-type compounds based on a 1,4- diaryl-1-thio-1, 3-butadiene conjugated
system in a dibenzobarrelene skeleton, Journal of Organic Chemistry, 2015,
80, 11598-11604.
3.L. Xue, J. He, X. Gu, Z. Yang, B. Xu, W. Tian, Efficient bulk heterojunction
solar cells based on a symmetrical D-π-A-π-D organic dye molecule, Journal
of Physical Chemistry C, 2009, 113, 12911-12917.
4.X. Qian,R. Yan,C. Xu,L. Shao,H. Li,L. Hou, New effcient organic dyes
employing indeno[1,2-b]indole as the donor moiety for dye-sensitized solar
cells, Journal of Power Sources, 2016, 332, 103-110.
5.W. Zhang, Y. Wu, H. Zhu, Q. Chai; J. Liu; H. Li, X. Song, W. Zhu, Rational
molecular engineering of indoline-based D A-π A organic sensitizers for
long-wavelength-responsive dye-sensitized solar cells, ACS Applied Materials
& Interfaces, 2015, 7, 26802-26810.
6.S. Dai, F. Zhao, Q. Zhang ,T.Lau, T. Li, K. Liu, Q. Ling, C.Wang, X. Lu, W.
You, X.Zhan,Fused nonacyclic electron acceptors for efficient polymer solar
cells, Jorunal of the American, 2017, 139, 1336-1343.
7.Y. Li, Z. Wang, X. Li, G. Xie, D. Chen, Y. Wang, C. Lo, A. Lien, J. Peng, Y.
Cao, S. Su, Highly Efficient Spiro fluorene-9,9 'thioxanthene core derived
blue emitters and fluorescent/phosphorescent hybrid white organic light-
emitting diodes, Chemistry of Materials, 2015, 27, 1100-1109.
8.Ye.O.Shaydyuk, S.M.Levchenko, S.A.Kurhuzenkau, D.Anderson, A.E.Masunov,
O.D.Kachkovsky, Yu.L.Slominsky, J.L.Bricks, K.D.Belfield, M.V. Bondar,
Linear photophysics, two-photon absorption and femtosecond transient
absorption spectroscopy of styryl dye bases, Journal of Luminescence, 2017,
183, 360-367.
9.S. Kato,T. Matsumoto,M. Shigeiwa,H. Gorohmaru, S. Maeda, T. Ishi-i, S.
Mataka,Novel 2,1,3-benzothiadiazole-based red-fluorescent dyes with enhanced
two-photon absorption cross sections, Chemistry : A European Journal, 2006,
12, 2303-2317.
10.C. Sun, S. Lv, Y. Liu, Q. Liao, H. Zhang, H. Fu, J. Yao, Benzoindolic
squaraine dyes with a large two-photon absorption cross-section, Journal of
Materials Chemistry C, 2017, 5, 1224-1230.
11.X. Zhang, Z. Xu, Z. Ge, X. Ouyang, W. Ji, Tunable molecular configuration
for significant enhancement oftwo-photon absorption based on novel octupolar
benzoimidazolederivatives, Journal of Photochemistry and Photobiology A:
Chemistry, 2014, 290, 22-30.
12.J. Xiang, X. Cai, X. Lou, G. Feng, X. Min,W. Luo,BHe, C.Goh, L.Ng, J. Zhou,
Z.Zhao,B. Liu, B. Tang, Biocompatible green and red fluorescent organic
dots with remarkably large two-photon action cross sections for targeted
cellular imaging and real-time intravital blood vascular visualization, ACS
Applied Materials & Interfaces, 2015, 7, 14965-14974.
13.Tatiana V. Esipova; Sergei A. Vinogradov, Synthesis of Phosphorescent
Asymmetrically π-extended porphyrins for two photon applications, The
Journal of Organic Chemistry, 2014, 79, 8812-8825
14.T. Lin, Y. Lee, B. Huang, M. Tsai, J. Lin, Functionalized
tetrafluorenylethylene-type chromophores: Synthesis,two-photon absorption
and effective optical power-limiting properties in the visible-to-near IR
region, Dyes and Pigments, 2016, 134, 325-333.
15.Y. Lv,P.Liu, H.Ding,Y. Wu,Y. Yan,H. Liu,X. Wang,F. Huang, Y. Zhao,Z. Tian,
Conjugated polymer-based hybrid nanoparticles with two-photon excitation
and near-infrared emission features for fluorescence bioimaging within the
biological window, ACS Applied Materials & Interfaces, 2015, 7, 20640-
20648.
16.P. Liu, S. Li, Y. Jin, L. Qian, N. Gao, S. Yao, F.Huang, Q. Xu, Y. Cao,
Red-emitting DPSB-based conjugated polymer nanoparticles with high two-
photon brightness for cell membraneimaging, ACS Applied Materials &
Interfaces, 2015, 7, 6754-6763.
17.R. Guan, H. Wang,Q. Zhang,J. Wu,Y. Tian, Mitochondria-specific imaging in
living cells with two-photon absorption small molecule containing amino
groups, Dyes and Pigments, 2017, 136, 473-479.
18.L. Hua, H. Wang,X. Xu, M. Zhang, X. Tian,J. Wu,H. Zhou, J. Yang, Y. Tian, A
small-molecule with large two-photon action cross-section servesas the
membrane-permeable probe for live cells imaging and bacteriaviability,
Sensors and Actuators B, 2017, 241, 1082-1089.
19.J. Schmitt, V. Heitz, A. Sour, F. Bolze, H. Ftouni, J. Nicoud, L. Flamigni,
B. Ventura, Diketopyrrolopyrrole-Porphyrin conjugates with high two-photon
absorption and singlet oxygen generation for two-photon Photodynamic
therapy, Angewandte Chemie International Edition, 2015, 54, 169-173.
20.O. Mongin, M. Sankar, M. Charlot, Y. Mir, M. Blanchard-Desce, Strong
enhancement of two-photon absorption properties in synergic ‘semi-
disconnected’ multiporphyrin assemblies designed for combined imaging and
photodynamic therapy, Tetrahedron Letters, 2013, 54, 6474-6478.
21.Q. Zou, H.Zhao, Y.Zhao, Y.Fang, D. Chen, J. Ren,X. Wang, Y. Wang, Y. Gu,F.
Wu, Effective two-photon excited photodynamic therapy of xenograft tumors
sensitized by water-soluble bis(arylidene)cycloalkanone photosensitizers,
Journal of Medicinal Chemistry, 2015, 58, 7949-7958.
22.X. Shen, L. Li, A. Chan, N. Gao, S. Yao, Q. Xu, Water-Soluble Conjugated
polymers for simultaneous two-photon cell Imaging and two-photon
photodynamic therapy, Advanced Optical Materials, 2013, 1, 92-99.
23.S. Picard; G. Clermont; Emilie Genin; Mireille Blanchard-Desce, 8-Br-
quinoline derivatives as sensitizers combining two-photon induced
fluorescence and singlet oxygen generation, Tetrahedron, 2015, 71, 1088-
1094.
24.Q. Zou, Y. Fang, Y. Zhao, H. Zhao, Y. Wang, Y. Gu, F. Wu, Synthesis and in
vitro photocytotoxicity of coumarin derivatives for one- and two-photon
excited photodynamic therapy, Journal of Medicinal Chemistry, 2013, 56,
5288-5294.
25.T. Lin,Y. Lee,B. Huang,M. Tsai,J. Lin,Functionalized
tetrafluorenylethylene-type chromophores: Synthesis,two-photon absorption
and effective optical power-limiting properties in the visible-to-near IR
region, Dyes and Pigments, 2016, 134, 325-333.
26.I. N. Tarabara,A. O. Kas’yan,O. V. Krishchik, S. V. Shishkina, O. V.
Shishkin, L. I. Kas’yan, Synthesis, structure, and transformations of new
endic anhydride derivatives, Journal of Organic Chemistry, 2002, 38, 1299-
1308.
27.S. AINeyadi, A. Salem, M. Ghattas, N. Atatreh, I. Abdou, Antibacterial
activity and mechanism of action of the benzazole acrylonitrile-based
compounds : In vitro, spectroscopic, and docking studies, European Journal
of Medicinal Chemistry, 2017, 136, 270-282.
28.G. Han, D. Kim, Y. Park, J. Bouffard, Y. Kim,Excimers Beyond Pyrene: A far-
red optical proximity reporter andits application to the label-free
detection of DNA, Angewandte Communications, 2015, 54, 3912-3916.

QRCODE
 
 
 
 
 
                                                                                                                                                                                                                                                                                                                                                                                                               
第一頁 上一頁 下一頁 最後一頁 top