博碩士論文 106223603 詳細資訊




以作者查詢圖書館館藏 以作者查詢臺灣博碩士 以作者查詢全國書目 勘誤回報 、線上人數:138 、訪客IP:3.145.14.167
姓名 瑞斯奇(Rizki Rachmad Saputra)  查詢紙本館藏   畢業系所 化學學系
論文名稱
(Development of Novel Two-photon Active Chromophores Derived from Thiazolothiazole Unit)
相關論文
★ 含五苯荑及異參茚并苯衍生物之合成與光物理行為之研究★ 具雙光子吸收行為之染料分子的合成與其光學性質探討
★ 新型雙光子吸收材料的分子設計與合成及其光學性質的探討★ 新型多叉及樹枝狀染料分子的合成及其非線性光學性質探討
★ 新穎多叉型之雙光子吸收材料的分子設計、合成與光學性質探討★ 新型四取代乙烯類及喹喔啉類染料分子的合成及其光學性質探討
★ 新型具喹喔啉、三嗪和吡嗪結構之染料分子 的合成及其光學性質探討★ Synthesis and Nonlinear Optical Property Characterizations of Novel Chromophores with Extended π-Conjugation Derived from Functionalized Fluorene Units
★ 含四取代乙烯及類喹喔啉結構單元之多分岐染料分子的合成與其非線性光學性質探討★ Synthesis and Nonlinear Optical Property Characterizations of Novel Fluorophores with Multi-Quinoxalinyl Units
★ 新型含茚并喹喔啉結構單元之樹狀共軛染料分子的合成與其非線性光學性質探討★ 含四取代乙烯乙炔及類喹喔啉結構單元之多分歧染料分子的合成與非線性光學性質探討
★ Two-Photon Absorption and Optical Power-limiting Properties of Three- and Six-Branched Chromophores Derived from 1,3,5-Triazine and Fluorene Units★ 新型含喹喔啉及各類拉電子基之染料分子的合成及其非線性光學性質探討
★ 含咔唑、芴及茚并喹喔啉等雜環單元之共軛染料分子的合成 與其非線性光學性質探討★ 合成各類以雜環為核心的分子並研究其非線性光學性質
檔案 [Endnote RIS 格式]    [Bibtex 格式]    [相關文章]   [文章引用]   [完整記錄]   [館藏目錄]   至系統瀏覽論文 ( 永不開放)
摘要(中) 本論文成功合成出含有thiazolothiazole為拉電子基團之模型分子,並完成其線性與非線性光學實驗。非線性光學實驗上利用飛秒脈衝式雷射來激發模型分子,測得其螢光以實驗證明為雙光子機制所誘發之螢光,模型分子1b在800nm光源激發下具有很強的雙光子激發螢光,並在680nm到850nm之間具有良好的雙光子特性(GM> 500),其模型分子在光學功率限幅器與光學功率穩定器之應用上具有很大的潛力。
摘要(英) Two new chromophores using thiazolothiazole as the electron-acceptor and diphenylaminofluorene/diphenylaminofluorene-thiophene as the electron-donor are synthesized and characterized for their linear and non-linear optical properties through corresponding methods. It is found that compound 1b exhibits strong two-photon induced fluorescence under irradiation of femtosecond laser at 800 nm. Two-photon absorption spectrum of chromophores 1b is mapped out by using two-photon excited fluorescence (2PEF) method and it is realized that this chromophore manifests intense two-photon activities (>500 GM) in the spectral range of 680-850 nm, which makes it a potential candidate for optical power-limiter or optical power-stabilizer.
關鍵字(中) ★ 雙光子吸收
★ Thiazolothiazole
★ 雙光子誘導熒光
關鍵字(英) ★ Two-photon absorption
★ Thiazolothiazole
★ Two-photon-induced fluorescence
論文目次 中文摘要 i
ABSTRACT ii
ACKNOWLEDGEMENTS iii
TABLE OF CONTENTS iv
LIST OF FIGURES vi
LIST OF TABLES ix
CHAPTER 1 INTRODUCTION AND OVERVIEW 1
1.1. Background 1
1.2. Two-Photon Absorption 4
1.2.1. Molecular Orbital Description 6
1.2.2. Excited State 8
1.3. Strategies for Design Structure 9
1.3.1. Linear Chromophores 13
1.3.2. Dipolar Molecules 14
1.3.3. Quadrupolar Molecules 15
1.3.4. Core and Central Bridges 16
1.3.5. Length of Conjugation System in Chromophore 18
1.4. Experimental Techniques Used to Quantify 2PA 19
1.4.1. TPEF (Two-Photon-Excited Fluorescence) 19
1.4.2. Nonlinear Transmission and Z-Scan Technique 20
1.5. Applications of Two-Photon Absorption 23
1.5.1. Photoactivation 23
1.5.2. Optical Power Limiting 24
1.5.4. Organic Solar Cells 27
CHAPTER 2 EXPERIMENTAL SECTION 29
2.1. Design and Synthesis 29
2.1.1. Thiazolothiazole Core 30
2.2. Measuring instruments and Methods 32
2.2.1. Linear Optical Measurements 32
• Absorption Measurement 32
• Emission Measurement 33
• Fluorescence Quantum Yield 34
• Fluorescence lifetime 36
2.2.2. Non-Linear Optical Measurements 36
CHAPTER 3 RESULTS AND DISCUSSION 40
3.1. Synthesis Explanation 40
3.2. One-Photon UV-Vis Spectral Properties 42
3.3. Non-linear Properties of TTZ Series 47
CHAPTER 4 CONCLUSION 51
CHAPTER 5 SYNTHESIS DETAIL 53
5.1. Synthesis Procedure 53
5.2 NMR Spectra 62
REFERENCES 76
參考文獻 [1] A. Gaur, H. Syed, B. Yendeti, and V. R. Soma, "Experimental evidence of two-photon absorption and its saturation in malachite green oxalate: a femtosecond Z-scan study," JOSA B, vol. 35, pp. 2906-2914, 2018.
[2] H. M. Kim and B. R. Cho, "Two-photon materials with large two-photon cross sections. Structure–property relationship," Chemical Communications, pp. 153-164, 2009.
[3] M. Pawlicki, H. A. Collins, R. G. Denning, and H. L. Anderson, "Two‐photon absorption and the design of two‐photon dyes," Angewandte Chemie International Edition, vol. 48, pp. 3244-3266, 2009.
[4] J. H. Strickler and W. W. Webb, "Two-photon excitation in laser scanning fluorescence microscopy," in CAN-AM Eastern′90, 1991, pp. 107-119.
[5] D. A. Parthenopoulos and P. M. Rentzepis, "Three-dimensional optical storage memory," Science, vol. 245, pp. 843-845, 1989.
[6] J. H. Strickler and W. W. Webb, "Three-dimensional optical data storage in refractive media by two-photon point excitation," Optics letters, vol. 16, pp. 1780-1782, 1991.
[7] W. Denk, J. H. Strickler, and W. W. Webb, "Two-photon laser scanning fluorescence microscopy," Science, vol. 248, pp. 73-76, 1990.
[8] P. Sperber and A. Penzkofer, "S 0-S n two-photon absorption dynamics of rhodamine dyes," Optical and quantum electronics, vol. 18, pp. 381-401, 1986.
[9] L. W. Tutt and T. F. Boggess, "A review of optical limiting mechanisms and devices using organics, fullerenes, semiconductors and other materials," Progress in quantum electronics, vol. 17, pp. 299-338, 1993.
[10] M. Albota, D. Beljonne, J.-L. Brédas, J. E. Ehrlich, J.-Y. Fu, A. A. Heikal, et al., "Design of organic molecules with large two-photon absorption cross sections," Science, vol. 281, pp. 1653-1656, 1998.
[11] M. Rumi, J. E. Ehrlich, A. A. Heikal, J. W. Perry, S. Barlow, Z. Hu, et al., "Structure− property relationships for two-photon absorbing chromophores: bis-donor diphenylpolyene and bis (styryl) benzene derivatives," Journal of the American Chemical Society, vol. 122, pp. 9500-9510, 2000.
[12] B. A. Reinhardt, L. L. Brott, S. J. Clarson, A. G. Dillard, J. C. Bhatt, R. Kannan, et al., "Highly active two-photon dyes: design, synthesis, and characterization toward application," Chemistry of Materials, vol. 10, pp. 1863-1874, 1998.
[13] Y. S. Yao, J. Xiao, X. S. Wang, Z. B. Deng, and B. W. Zhang, "Starburst DCM‐Type Red‐Light‐Emitting Materials for Electroluminescence Applications," Advanced functional materials, vol. 16, pp. 709-718, 2006.
[14] H. J. Lee, J. Sohn, J. Hwang, S. Y. Park, H. Choi, and M. Cha, "Triphenylamine-cored bifunctional organic molecules for two-photon absorption and photorefraction," Chemistry of Materials, vol. 16, pp. 456-465, 2004.
[15] M. Rumi and J. W. Perry, "Two-photon absorption: an overview of measurements and principles," Advances in Optics and Photonics, vol. 2, pp. 451-518, 2010.
[16] F. Terenziani, C. Katan, E. Badaeva, S. Tretiak, and M. Blanchard‐Desce, "Enhanced two‐photon absorption of organic chromophores: theoretical and experimental assessments," Advanced Materials, vol. 20, pp. 4641-4678, 2008.
[17] S. R. Marder, "Organic nonlinear optical materials: where we have been and where we are going," Chemical communications, pp. 131-134, 2006.
[18] B. Strehmel and V. Strehmel, "Two-photon physical, organic, and polymer chemistry: theory, techniques, chromophore design, and applications," Advances in Photochemistry, vol. 29, pp. 111-354, 2007.
[19] W. L. Peticolas, "Multiphoton spectroscopy," Annual Review of Physical Chemistry, vol. 18, pp. 233-260, 1967.
[20] W. M. McClain, "Two-photon molecular spectroscopy," Accounts of Chemical Research, vol. 7, pp. 129-135, 1974.
[21] J. R. Lakowicz, Principles of fluorescence spectroscopy: Springer Science & Business Media, 2013.
[22] T.-C. Lin, S.-J. Chung, K.-S. Kim, X. Wang, G. S. He, J. Swiatkiewicz, et al., "Organics and polymers with high two-photon activities and their applications," in Polymers for Photonics Applications II, ed: Springer, 2003, pp. 157-193.
[23] J. Ehrlich, X. Wu, I.-Y. Lee, Z.-Y. Hu, H. Röckel, S. Marder, et al., "Two-photon absorption and broadband optical limiting with bis-donor stilbenes," Optics Letters, vol. 22, pp. 1843-1845, 1997.
[24] W. L. Peticolas, J. P. Goldsborough, and K. Rieckhoff, "Double photon excitation in organic crystals," Physical Review Letters, vol. 10, p. 43, 1963.
[25] O. Mongin, L. Porrès, M. Charlot, C. Katan, and M. Blanchard‐Desce, "Synthesis, Fluorescence, and Two‐Photon Absorption of a Series of Elongated Rodlike and Banana‐Shaped Quadrupolar Fluorophores: A Comprehensive Study of Structure–Property Relationships," Chemistry–A European Journal, vol. 13, pp. 1481-1498, 2007.
[26] M. H. Werts, S. Gmouh, O. Mongin, T. Pons, and M. Blanchard-Desce, "Strong modulation of two-photon excited fluorescence of quadripolar dyes by (de) protonation," Journal of the American Chemical Society, vol. 126, pp. 16294-16295, 2004.
[27] R. W. Boyd, Nonlinear optics: Elsevier, 2003.
[28] R. Sutherland, "Handbook of nonlinear optics Marcel Dekker Inc," New York, 1996.
[29] M. Sheik-Bahae, A. A. Said, T.-H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE journal of quantum electronics, vol. 26, pp. 760-769, 1990.
[30] P. Chapple, J. Staromlynska, J. Hermann, T. Mckay, and R. McDuff, "Single-beam Z-scan: measurement techniques and analysis," Journal of Nonlinear Optical Physics & Materials, vol. 6, pp. 251-293, 1997.
[31] P. Tian and W. S. Warren, "Ultrafast measurement of two-photon absorption by loss modulation," Optics letters, vol. 27, pp. 1634-1636, 2002.
[32] K. A. Korzycka, P. M. Bennett, E. J. Cueto-Diaz, G. Wicks, M. Drobizhev, M. Blanchard-Desce, et al., "Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan," Chemical science, vol. 6, pp. 2419-2426, 2015.
[33] C. Bauer, B. Schnabel, E. B. Kley, U. Scherf, H. Giessen, and R. F. Mahrt, "Two‐Photon Pumped Lasing from a Two‐Dimensional Photonic Bandgap Structure with Polymeric Gain Material," Advanced Materials, vol. 14, pp. 673-676, 2002.
[34] Z. M. Wang and A. Neogi, Nanoscale photonics and optoelectronics vol. 9: Springer, 2010.
[35] D. Riehl, N. Izard, L. Vivien, E. Anglaret, E. Doris, C. Ménard, et al., "Broadband optical limiting optimization by combination of carbon nanotubes and two-photon absorbing chromophores in liquids," in Nonlinear Optical Transmission and Multiphoton Processes in Organics, 2003, pp. 124-135.
[36] P. L. Baldeck, Y. Morel, M. Plazanet, P. Feneyrou, C. Andraud, T. Brotin, et al., "Optical limiting properties of organic nonlinear crystals," in Nonlinear Optical Properties of Organic Materials X, 1997, pp. 112-118.
[37] S. Marder and J. Perry, "Two-photon or higher-order absorbing optical materials and methods of use," ed: Google Patents, 2001.
[38] H. S. Nalwa and S. Miyata, Nonlinear optics of organic molecules and polymers: CRC press, 1996.
[39] C. W. Spangler, J. R. Starkey, F. Meng, A. Gong, M. Drobizhev, A. Rebane, et al., "Targeted two-photon photodynamic therapy for the treatment of subcutaneous tumors," in Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy XIV, 2005, pp. 141-149.
[40] C. Spangler and A. Rebane, "Multifunctional photodynamic agents for treating of disease," ed: Google Patents, 2004.
[41] P. Cheng, Q. Shi, Y. Lin, Y. Li, and X. Zhan, "Evolved structure of thiazolothiazole based small molecules towards enhanced efficiency in organic solar cells," Organic Electronics, vol. 14, pp. 599-606, 2013.
[42] G. S. He, T.-C. Lin, P. N. Prasad, R. Kannan, R. A. Vaia, and L.-S. Tan, "Study of two-photon absorption spectral property of a novel nonlinear optical chromophore using femtosecond continuum," The Journal of Physical Chemistry B, vol. 106, pp. 11081-11084, 2002.
[43] G. B. Smith, G. C. Dezeny, D. L. Hughes, A. O. King, and T. R. Verhoeven, "Mechanistic studies of the Suzuki cross-coupling reaction," The Journal of Organic Chemistry, vol. 59, pp. 8151-8156, 1994.
[44] H. C. Zhang, E. Q. Guo, Y. L. Zhang, P. H. Ren, and W. J. Yang, "Donor− acceptor-substituted anthracene-centered cruciforms: synthesis, enhanced two-photon absorptions, and spatially separated frontier molecular orbitals," Chemistry of Materials, vol. 21, pp. 5125-5135, 2009.
[45] D. L. Pavia, G. M. Lampman, G. S. Kriz, and J. A. Vyvyan, Introduction to spectroscopy: Cengage Learning, 2008.
[46] H. Zhou, Z. Zheng, G. Xu, Z. Yu, X. Yang, L. Cheng, et al., "1, 3, 5-Triazine-cored derivatives dyes containing triphenylamine based two-photon absorption: Synthesis, optical characterization and bioimaging," Dyes and Pigments, vol. 94, pp. 570-582, 2012.
[47] J. Shao, Z. Guan, Y. Yan, C. Jiao, Q.-H. Xu, and C. Chi, "Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores," The Journal of organic chemistry, vol. 76, pp. 780-790, 2011.
[48] D. Zhang, Y. Gao, J. Dong, Q. Sun, W. Liu, S. Xue, et al., "Two-photon absorption and piezofluorochromism of aggregation-enhanced emission 2, 6-bis (p-dibutylaminostyryl)-9, 10-bis (4-pyridylvinyl-2) anthracene," Dyes and Pigments, vol. 113, pp. 307-311, 2015.
指導教授 林子超(Lin, Tzu-Chau) 審核日期 2019-8-21
推文 facebook   plurk   twitter   funp   google   live   udn   HD   myshare   reddit   netvibes   friend   youpush   delicious   baidu   
網路書籤 Google bookmarks   del.icio.us   hemidemi   myshare   

若有論文相關問題,請聯絡國立中央大學圖書館推廣服務組 TEL:(03)422-7151轉57407,或E-mail聯絡  - 隱私權政策聲明