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研究生：	許秉豐 Hsu, Ping-Feng
論文名稱：	希夫鹼修飾之芘衍生物的合成及其金屬離子螢光感測特性 A novel pyrene-Schiff base fluorescent ‘turn on’ sensor toward Zn2+ and Al3+ with aggregation-induced emission enhancement
指導教授：	陳雲 Chen, Yun
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：	2016
畢業學年度：	104
語文別：	英文
論文頁數：	56
中文關鍵詞：	螢光感測器、希夫鹼、芘、光誘導電子轉移、凝集誘導發光
外文關鍵詞：	fluorescent sensor, pyrene, Schiff base, photoinduced electron transfer, aggregation-induced emission enhancement
相關次數：	點閱：71 下載：1
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本研究合成出以希夫鹼修飾之芘衍生物(PySb)作為金屬離子螢光感測器，此PySb在光誘導電子轉移(photoinduced electron transfer, PET)的作用下，螢光強度非常低。當PySb溶於乙醇溶液中時，加入鋅離子可抑制光誘導電子轉移的發生進而促使螢光增強(λem = 470 nm)。而在二甲基亞碸溶液中，則換成加入鋁離子可抑制光誘導電子轉移的發生進而促使螢光增強(λem = 458 nm)。由核磁共振儀之鑑定亦證實PySb分別與鋅、鋁離子形成錯合物。此外，PySb與鋅離子之螯合比(1:2)、結合常數(2×109 M-1)、偵測極限(2.39×10-8 M) 分別由Job plot和滴定實驗測得。當PySb與鋅離子溶於二甲基甲醯胺中時，增加乙醇的含量可誘發凝集誘導螢光增強效應(aggregation-induced emission enhancement)，使得螢光強度更進一步的增強。PySb在pH = 3至pH = 11的溶液中皆可有效的作為金屬離子螢光感測器，而在pH = 12 之溶液中則因分子內電荷轉移(intramolecular charge transfer)之機制放出綠光(λem = 515 nm)。

A novel fluorescent sensor PySb comprising of pyrene moiety as the fluorophore, benzene ring as the spacer, and 2-(hydroxymethyl)propane-1,3-diol as the ionophore was synthesized. PySb itself exhibited weak fluorescence due to photoinduced electron transfer (PET). It can serve as a highly selective and sensitive fluorescent ‘turn on’ sensor toward (a) Zn2+ in ethanol solution (λem = 470 nm) and (b) Al3+ in DMSO solution (λem = 458 nm). The complexes of PySb-Zn2+ and PySb-Al3+ were further supported by 1H NMR spectra. The 1:2 stoichiometry between PySb and Zn2+ was obtained from Job plot. Excellent detection limit toward Zn2+ (2.39×10-8 M) was derived from titration experiment. Similarly, the binding constant toward Zn2+ was estimated as 2×109 M-1 based on titration experiment. PySb-Zn2+ complex in DMF solution showed aggregation-induced emission enhancement with increasing content of ethanol (0-99%). It could be utilized as a fluorescent sensor in a wide range of pH (3-11). Green emission of PySb (λem = 515 nm) was observed when pH was higher than 12 due to intramolecular charge transfer (ICT).

Table of contents

摘要	I
Abstract	II
致謝	III
Table of contents	IV
List of scheme	VI
List of tables	VI
List of figures	VI
Chapter 1	1
Introduction	1
1-1 Introduction to fluorescent sensor	1
1-2 Photoinduced electron transfer (PET)	2
1-2-1 Mechanism [15]	2
1-2-2 PET sensors	3
1-3 Introduction to Schiff base	5
1-4 Progress of PET sensors based on Schiff base moieties	6
1-5 Research motivation	7
Chapter 2	8
Theoretical background	8
2-1 Theory of photoluminescence[43-45]	8
2-1-1 Pauli exclusion principle	8
2-1-2 Photoluminescence energy level	9
2-1-3 Deactivation processes	10
2-1-3-1 Vibration relaxation	10
2-1-3-2 Internal conversion	10
2-1-3-3 External conversion	10
2-1-3-4 Intersystem conversion	11
2-1-3-5 Fluorescence and phosphorescence	11
2-2 Aggregation-induced emission (AIE) [46]	12
2-3 Suzuki reaction [59]	15
Chapter 3	16
Experimental Section	16
3-1 Instruments of Chemical Synthesis	16
3-2 Measurements	17
3-3 Preparation of Metal Ion Solutions and Titration	18
3-4 Materials	18
3-5 Synthetic Scheme of fluorescent sensor PySb	20
3-6 Synthesis of fluorescent sensor PySb	21
5,5'-(pyrene-2,7-diyl)bis(2-hydroxybenzaldehyde) (1)	21
2,2'-((1E,1'E)-((pyrene-2,7-diylbis(2-hydroxy-5,1-phenylene))bis(methanylylidene))bis(azanylylidene))bis(2-(hydroxymethyl)propane-1,3-diol) (PySb)	21
Chapter 4	22
Results and discussion	22
4-1 Synthesis and Characterization	22
4-1-1 1H NMR of PySb	22
4-1-2 Mass spectra of PySb	23
4-1-3 Elemental Analysis and yields	23
4-2 Optical Properties in ethanol solution	26
4-2-1 UV-Vis spectra	26
4-2-2 Fluorescence spectra	27
4-2-3 Time dependency	29
4-2-4 Job plot	30
4-2-5 Titration experiment	31
4-2-6 Binding Constant	32
4-2-7 Detection limit	33
4-2-8 Competition effect from other metal ions	34
4-2-9 Aggregation-induced emission enhancement (AIEE)	35
4-2-10 Influence of pH	38
4-3 1H NMR of PySb-Zn2+ complex	41
4-4 Optical properties in DMSO solution	42
4-4-1 UV-Vis spectra	42
4-4-2 Fluorescence spectra	43
4-4-3 Titration experiment	44
4-4-4 Competition effect from other metal ions	46
4-5 1H NMR of PySb-Al3+ complex	47
Chapter 5	48
Conclusion	48
References	49


List of scheme
Scheme 3-5-1. Synthetic procedures of PySb.	20


List of tables
Table 2-1-1. Rates of absorption and emission.	9
Table 4-1-1. Elemental analysis and reaction yields of PySb and compound 1.	23


List of figures
Figure 1-2-1. Structure and mechanism of PET sensors.	2
Figure 1-2-2. Examples of PET sensors.	4
Figure 1-3-1. General structure of Schiff base.	5
Figure 1-3-2. Structure of Salen ligand.	5
Figure 1-3-3. enol-keto tautomerism of Schiff base.	5
Figure 1-4-1. Examples of PET sensors based on Schiff base moieties.	6
Figure 2-1-1. The electron spins of the ground state and excited states.	8
Figure 2-1-2. The energy-level diagram for a typical photoluminescent molecule.	9
Figure 2-1-3. Deactivation processes.	10
Figure 2-2-1. Structure of hexaphenylsilole (HPS).	13
Figure 2-2-2. Examples that utilized AIE effect.	14
Figure 2-3-1. Mechanism of Suzuki reaction.	15
Figure 3-2-1. Four types of absorption transition.	17
Figure 4-1-1. 1H NMR spectrum of compound 1.	24
Figure 4-1-2. 1H NMR spectrum of PySb.	24
Figure 4-1-3. Mass spectra of PySb.	25
Figure 4-1-4. Isotope pattern of PySb.	25
Figure 4-2-1. UV-Vis spectra of PySb (10-5 M) with various metal ions (2×10-4 M) in HEPES buffer solution (Ethanol/H2O = 9/1, v/v).	26
Figure 4-2-2. PET mechanism of PySb.	27
Figure 4-2-3. Fluorescence spectra of PySb (10-5 M) with various metal ions (2×10-4 M) in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v), λex = 309 nm.	28
Figure 4-2-4. Photograph of PySb (10-5 M) with various metal ions (2×10-4 M) in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v) under UV-light.	28
Figure 4-2-5. Fluorescence spectra of PySb (0.5×10-5 M) with Zn2+ (9.5×10-5 M) in ethanol, λex = 309 nm.	29
Figure 4-2-6. Job plot of PySb and Zn2+ in in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v). The total concentration of PySb and Zn2+ was 10-5 M (λex = 309 nm, λem = 470 nm).	30
Figure 4-2-7. Fluorescence spectra of PySb (10-5 M) with increasing amount of Zn2+ in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v), (λex = 309 nm, λem = 470 nm).	31
Figure 4-2-8. Benesi–Hildebrand plot of PySb, assuming 1:2 stoichiometry for association between PySb and Zn2+ in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v).	32
Figure 4-2-9. Detection limit of PySb (10-5 M) toward Zn2+ in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v).	33
Figure 4-2-10. Fluorescence spectra of PySb (10-5 M) with various metal ions (2×10-5 M) in HEPES buffer solutions (Ethanol/H2O = 9/1, v/v), λex = 309 nm.	34
Figure 4-2-11. Fluorescence spectra of PySb (10-5 M) with Zn2+ (2×10-4 M) in different DMF/ethanol ratio solutions (λex = 324 nm, λem =470 nm).	36
Figure 4-2-12. UV-Vis spectra of PySb (10-5 M) with Zn2+ metal ion (2×10-4 M) in DMSO and ethanol solutions.	37
Figure 4-2-13. Fluorescence spectra of PySb (10-5 M) in different pH solutions (Ethanol/H2O = 9/1, v/v), λex = 309 nm.	39
Figure 4-2-14. Formation of phenolate at high pH.	39
Figure 4-2-15. Fluorescence spectra of PySb (10-5 M) with Zn2+ (2×10-4 M) in different pH solutions (Ethanol/H2O = 9/1, v/v), λex = 309 nm.	40
Figure 4-2-16. Photograph of PySb (10-5 M) with Zn2+ (2×10-4 M) in different pH solutions (left: pH = 7.0, right: pH = 12.0) under UV-light.	40
Figure 4-2-17. Competition between PET and ICT mechanisms.	40
Figure 4-3-1. 1H NMR of free PySb (bottom), PySb +Zn2+ (middle), and PySb+Zn2++D2O (upper).	41
Figure 4-4-1. UV-Vis spectra of PySb (10-5 M) with Zn2+ and Al3+ metal ions (2×10-4 M) in HEPES buffer solution (DMSO/H2O = 9/1, v/v).	42
Figure 4-4-2. Fluorescence spectra of PySb (10-5 M) with various metal ions (2×10-4 M) in HEPES buffer solutions (DMSO/H2O = 9/1, v/v), λex = 309 nm.	43
Figure 4-4-3. Fluorescence spectra of PySb (10-5 M) with increasing amount of Al3+ in HEPES buffer solutions (DMSO/H2O = 9/1, v/v), (λex = 309 nm, λem = 458 nm).	45
Figure 4-4-4. Fluorescence spectra of PySb (10-5 M) with various metal ions (2×10-5 M) in HEPES buffer solutions (DMSO/H2O = 9/1, v/v), λex = 309 nm.	46
Figure 4-5-1. 1H NMR of free PySb (bottom), PySb +Al3+ (middle), and PySb+ Al3++D2O (upper).	47


                                    

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