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研究生：	林柏成 Lin, Po-Chen
論文名稱：	一、利用電子激發態分子探測釕金屬修飾蛋白質內的長距離電子傳遞及檢測十二烷基硫酸鈉的濃度二、七種台灣精油的化學組成及對大腸桿菌的抗菌效果 (I)Probing long range electron transfer in ruthenium modified proteins and evaluating the SDS concentration by using electronically excited molecules (II) Essential oils from Taiwan: chemical composition and antibacterial activity against Escherichia coli
指導教授：	張一知 Chang, I-Jy
學位類別：	博士 Doctor
系所名稱：	化學系 Department of Chemistry
論文出版年：	2016
畢業學年度：	105
語文別：	英文
論文頁數：	168
中文關鍵詞：	閃光淬熄法、細胞色素c 、雙分子淬熄反應、籠蔽效應、溴化乙錠、十二烷基硫酸鈉、臨界微胞濃度、檢測、抗菌性、化學組成、大腸桿菌、精油、氣相層析質譜儀
英文關鍵詞：	flash-quench, cytochrome c, bimolecular quenching reaction, cage effect, ethidium bromide, sodium dodecyl sulfate, critical micelle concentration, assay, antibacterial activity, chemical composition, Escherichia coli, essential oil, gas chromatography−mass spectrometry
DOI URL：	https://doi.org/10.6345/NTNU202204676
論文種類：	學術論文
相關次數：	點閱：192 下載：16
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本研究合成出釕金屬聯吡啶錯合物([Ru((CH3)2bpy)2(im)2]2+與[Ru((COO−)2bpy)2(im)2]2−)，並將其修飾在細胞色素c (cyt c)上，再藉由閃光淬熄法來探測蛋白質內的電子傳遞。修飾上推電子取代基的[Ru((CH3)2bpy)2(im)2]2+與Ru(NH3)63+反應後，得到25.1%的激發態淬熄率和42.0%的三價釕金屬([RuIII( )2(im)2]3+)生成率；修飾上拉電子取代基的[Ru((COO−)2bpy)2(im)2]2−則有65.2%激發態淬熄率和19.6%的三價釕金屬生成率。同樣將釕金屬修飾蛋白質與Ru(NH3)63+反應，發現Ru((CH3)2bpy)2(im)(His33)-Fe2+-cyt c的分子內電子傳遞之量子產率是17.6%，而Ru((COO−)2bpy)2(im)(His33)-Fe2+-cyt c的分子內電子傳遞之量子產率則是11.9%。儘管反應驅動力預測Ru((COO−)2bpy)2(im)(His33)-Fe2+-cyt c有較大的量子產率，但還要考慮另外兩個變數的影響(籠蔽效應跟化學反應)。
利用Ru(bpy)2dppz2+的光開關性質來檢測十二烷基硫酸鈉的濃度，隨著十二烷基硫酸鈉的濃度增加，Ru(bpy)2dppz2+的磷光強度也增加。然而，當十二烷基硫酸鈉的濃度小於0.1%時，Ru(bpy)2dppz2+會沉澱析出，因此換用溴化乙錠。在低濃度的十二烷基硫酸鈉(0−0.1%)，溴化乙錠的吸收波長最大值會紅位移而螢光強度會降低；當十二烷基硫酸鈉的濃度超過0.1%，溴化乙錠的吸收波長最大值會藍位移而螢光強度會增強；當十二烷基硫酸鈉的濃度超過臨界微胞濃度後，溴化乙錠的螢光強度維持不變。利用上述現象，溴化乙錠可以拿來檢測十二烷基硫酸鈉的濃度。
利用氣相層析質譜儀分離鑑定七種台灣精油，再透過NIST 08資料庫的比對，可以清楚辨識主要的化學成分。藉由定量分析的實驗，可以得知精油的主要成分含量，比較文獻後發現，不同產地的精油其組成成分會有很大的差異。將七種精油分別加入大腸桿菌培養液中，經過24小時後，發現廣藿香的抑菌效果非常好，只要0.05%的濃度就可以完全抑制大腸桿菌的生長；而丁香羅勒和甜馬鬱蘭的抑菌效果也不差，兩者的最低抑菌濃度都是0.1%。

Ruthenium bipyridine-type compounds, [Ru((CH3)2bpy)2(im)2]2+ and [Ru((COO−)2bpy)2(im)2]2−, were synthesized to evaluate the protein electron transfer property by flash-quench method. After reacting with Ru(NH3)63+, [Ru((CH3)2bpy)2(im)2]2+, with electron donating substitutents, gives quenching yield of 25.1% and formation yield of [RuIII( )2(im)2]3+ species of 42.0%. While [Ru((COO−)2bpy)2(im)2]2−, with electron withdrawing substitutents, has 65.2% of quenching yield and 19.6% of formation yield of [RuIII( )2(im)2]3+ species. In those ruthenium modified cytochrome c, Ru((CH3)2bpy)2(im)(His33)-Fe2+-cyt c has the largest quantum yield of intramolecular electron transfer (17.6%) and the smallest for Ru((COO−)2bpy)2(im)(His33)-Fe2+-cyt c (11.9%). Although driving force favors for Ru((COO−)2bpy)2(im)(His33)-Fe2+-cyt c, cage effect and chemical reaction are other variable factors in the trend.
Ru(bpy)2dppz2+, known for its light switch property, had been utilized to evaluate the concentration of SDS. As the concentration of SDS increases, the emission intensity of Ru(bpy)2dppz2+ increases. Unfortunately, at the attempt to lower the SDS concentration below 0.1%, Ru(bpy)2dppz2+ precipitates, therefore, ethidium bromide (EtdBr) was employed. In the low concentration of SDS (0−0.1%), the wavelength of absorption maximum red shifts and the emission intensity decreases. While the concentration of SDS is above 0.1%, the wavelength of absorption maximum blue shifts and the emission intensity is recovering. At above the CMC of SDS, the emission intensity remains unchanged and is higher than that without SDS. An assay for evaluating of SDS concentration by EtdBr has been proposed.
Chemical compositions of seven essential oils from Taiwan had been analyzed by gas chromatography−mass spectroscopy. The eluates had been identified by matching the mass fragment patents to the NIST 08 database. Quantitatively analysis showed the major components are somewhat different from the same essential oils reported that are obtained from other origins. The antibacterial activity of the essential oils against Escherichia coli was evaluated by optical density method. Patchouli is a very effective inhibitor that completely inhibits the growth of E. coli at 0.05%. Clove basil and sweet marjoram are good inhibitors and their upper limits of minimum inhibitory concentration are 0.1%.

Table of contents
List of Figures………………………………………………………………………...iv
List of Tables………………………………………………………………………...xiii
List of Schemes……………………………………………………………………...xiv


Chapter 1………………………………………………………………………………1
Abstract…………………………………………………………………………..2
Introduction………………………………………………………………………3
Experimental Section……………………………………………………………11
Results and Discussion………………………………………………………….18
Electronic absorption and emission spectra of ruthenium model compounds………………………………………………………………...18
Electrochemistry of ruthenium model compounds………………………..19
Radiative and non-radiative decay rate constant of ruthenium model compounds………………………………………………………………...20
Bimolecular quenching reaction of ruthenium model compounds………..22
Driving force dependence of the bimolecular quenching reaction………...24
Comparison of quenching rate constant and driving force of the bimolecular quenching reaction…………………………………………...26
Comparison of the excited state quenching yield and the formation yield of [RuIII(LL)2(im)2]3+ species……………………………………………...29
Photophysical properties of ruthenium modified Fe3+-cytochrome c……..33
Bimolecular quenching reaction of ruthenium modified Fe3+-cytochrome c…………………………………………………………35
Bimolecular quenching reaction of ruthenium modified Fe2+-cytochrome c…………………………………………………………38
Intramolecular electron transfer in ruthenium modified Fe2+-cytochrome c…………………………………………………………40
Driving force dependence of the intramolecular electron transfer reaction…………………………………………………………………….45
Conclusions……………………………………………………………………..49
References………………………………………………………………………51
Supporting Information…………………………………………………………54


Chapter 2……………………………………………………………………………..59
Abstract…………………………………………………………………………60
Introduction……………………………………………………………………..61
Experimental Section…………………………………………………………...65
Results and Discussion………………………………………………………….69
Interaction between Ru(bpy)2dppz2+ and surfactants……………………...69
UV−Visible absorption and luminescence spectra for Ru(bpy)2dppz2+ in SDS aqueous solution……………………………………………………...69
UV−Visible absorption and luminescence spectra for Ru(bpy)2dppz2+ in TX-100 and CTAB aqueous solution……………………………………...72
Summary of the interaction between Ru(bpy)2dppz2+ and surfactants……74
Interaction between EtdBr and surfactants………………………………...75
UV−Visible absorption and luminescence spectra for EtdBr in SDS aqueous solution…………………………………………………………...75
UV−Visible absorption and luminescence spectra for EtdBr in TX-100 aqueous solution…………………………………………….......................84
The effect of micelle formation for EtdBr in SDS and TX-100 aqueous solution…………………………………………………………………….88
UV−Visible absorption and luminescence spectra for EtdBr in CTAB aqueous solution…………………………………………….......................89
Solvatochromic effect for EtdBr in SDS aqueous solution………………..91
Detail discussion with the emissive property of EtdBr in SDS aqueous solution…………………………………………………………………….93
Surfactant chain length effect on the photophysical properties of EtdBr……………………………………………………………………..102
Assay of estimating for the concentration of SDS in aqueous solution….111
Conclusions……………………………………………………………………113
References……………………………………………………………………..116
Supporting Information………………………………………………………..120


Chapter 3……………………………………………………………………………131
Abstract………………………………………………………………………..132
Introduction……………………………………………………………………133
Experimental Section………………………………………………………….135
Results and Discussion………………………………………………………...139
Method development……………………………………………………..139
Qualitative and quantitative analysis of essential oils……………………142
Major component in Taiwan species and comparison with various origins…………………………………………………………………….146
High content of component and its application on biology………………148
Antibacterial activity against E. coli……………………………………..149
Conclusions……………………………………………………………………153
References……………………………………………………………………..154
Supporting Information………………………………………………………..158


List of Figures
Chapter 1
Figure 1. Photosynthetic electron transport chain……………………………………..4
Figure 2. Electron transport chain of cellular respiration……………………………...6
Figure 3. Latimer diagram of [Ru(bpy)3]2+ complex………………………………….7
Figure 4. Structure of the ruthenium model compounds……………………………..12
Figure 5. Structure of the ruthenium modified cytochrome c………………………..12
Figure 6. Electronic absorption and emission spectra of ruthenium model compounds in 50 mM NaPi buffer solution………………………………………….19
Figure 7. Cyclic voltammogram of ruthenium model compounds in 50 mM NaPi buffer solution………………………………………………………………………..20
Figure 8. Emission spectra of [Ru((COO−)2bpy)2(im)2]2− with various concentration of Rua63+………………………………………………………………22
Figure 9. Driving force (−deltaGQ) versus natural logarithm of quenching rate constant for the bimolecular quenching reaction between ruthenium model compound and Rua63+………………………………………………………………...25
Figure 10. Driving force dependence of electron transfer rate constants predicted by semi-classical Marcus theory………………………………………………………...27
Figure 11. Nanosecond transient absorption spectra of ruthenium model compounds without and with Rua63+ at the ground state bleach wavelength……………………..30
Figure 12. The absorption spectra of [Ru((CH3)2bpy)2(im)2]2+ with 5 mM Rua63+ before experiment, after emission measurement and after transient absorption measurement………………………………………………………………………….32
Figure 13. Electronic absorption spectra of ruthenium modified Fe3+-cyt c in 50 mM NaPi buffer solution……………………………………………………………..34
Figure 14. Emission spectra of ruthenium modified Fe3+-cyt c in 50 mM NaPi buffer solution………………………………………………………………………..35
Figure 15. Nanosecond transient absorption spectra of ruthenium modified Fe3+-cyt c with Rua63+ at the ground state bleach wavelength……………………….37
Figure 16. Difference absorption spectrum of oxidized and reduced form of cyt c….39
Figure 17. Nanosecond transient absorption spectra of ruthenium modified Fe2+-cyt c with Rua63+ at 550 nm…………………………………………………….41
Figure 18. Nanosecond transient absorption spectra of ruthenium modified Fe2+-cyt c with Rua63+ at 390 nm…………………………………………………….42
Figure 19. Nanosecond transient absorption spectrum of Ru(bpy)2(im)(His33)-Fe2+-cyt c with Rua63+ and the difference absorption spectrum of oxidized and reduced cyt c………………………………………………………...43
Figure 20. Nanosecond transient absorption spectrum of Ru((CH3)2bpy)2(im)(His33)-Fe2+-cyt c with Rua63+ and the difference absorption spectrum of oxidized and reduced dm-cyt c………………………………………….44
Figure 21. Nanosecond transient absorption spectrum of Ru((COO−)2bpy)2(im)(His33)-Fe2+-cyt c with Rua63+ and the difference absorption spectrum of oxidized and reduced dc-cyt c…………………………………………..44
Figure 22. Driving force (−deltaGET) versus natural logarithm of intramolecular electron transfer rate constant for the ruthenium modified Fe2+-cyt c……………….46
Figure 23. Driving force (−deltaGET) versus quantum yields of intramolecular electron transfer for the ruthenium modified Fe2+-cyt c………………………………………47


Figure S1. Emission spectra of [Ru(bpy)2(im)2]2+ with various concentrations of Rua63+………………………………………………………………………………...54
Figure S2. Emission spectra of [Ru((CH3)2bpy)2(im)2]2+ with various concentrations of Rua63+……………………………………………………………...54
Figure S3. The Stern-Volmer plot of emission intensity of [Ru(bpy)2(im)2]2+ with Rua63+…………………………………………………………………………...........55
Figure S4. The Stern-Volmer plot of emission lifetime of [Ru(bpy)2(im)2]2+ with Rua63+…………………………………………………………………………...........55
Figure S5. The Stern-Volmer plot of emission intensity of [Ru((CH3)2bpy)2(im)2]2+ with Rua63+…………………………………………………………………………...56
Figure S6. The Stern-Volmer plot of emission lifetime of [Ru((CH3)2bpy)2(im)2]2+ with Rua63+…………………………………………………………………………...56
Figure S7. The Stern-Volmer plot of emission intensity of [Ru((COO−)2bpy)2(im)2]2− with Rua63+………………………………………………57
Figure S8. The Stern-Volmer plot of emission lifetime of [Ru((COO−)2bpy)2(im)2]2− with Rua63+………………………………………………57
Figure S9. The Stern-Volmer plot of emission lifetime of [Ru(phen)2(im)2]2+ with Rua63+………………………………………………………………………………58


Chapter 2
Figure 1. Structure of EtdBr and Ru(bpy)2dppz2+……………………………………63
Figure 2. Structures of the three kinds of surfactants………………………………...69
Figure 3. UV−Visible absorption spectra for Ru(bpy)2dppz2+ in 0% and 2% of SDS…………………………………………………………………………………...70
Figure 4. Phosphorescence spectra for Ru(bpy)2dppz2+ between 0−2% of SDS…….71
Figure 5. Emission intensity at 635 nm for Ru(bpy)2dppz2+ between 0−2% of SDS…………………………………………………………………………………...72
Figure 6. UV−Visible absorption spectra for Ru(bpy)2dppz2+ in 0% and 2% of TX-100……………………………………………………………………………….73
Figure 7. UV−Visible absorption spectra for Ru(bpy)2dppz2+ in 0% and 2% of CTAB…………………………………………………………………………………74
Figure 8. UV−Visible absorption spectra for EtdBr in various concentrations of SDS…………………………………………………………………………………...76
Figure 9. UV−Visible absorption spectra for diluted EtdBr between 0−2% of SDS…………………………………………………………………………………...77
Figure 10. Fluorescence spectra for EtdBr in various concentrations of SDS……….78
Figure 11. Absorption maximum of n→pi* transition for EtdBr between 0−2% of SDS…………………………………………………………………………………...79
Figure 12. Job plot for EtdBr-SDS complex by monitoring the change of emission intensity at 615 nm…………………………………………………………80
Figure 13. Diagram of the interaction for (a) EtdBr-SDS complex and (b) EtdBr-SDS micelle…………………………………………………………………...81
Figure 14. Calculating the binding constant from the fitting curve for the plot of EtdBr emission intensity at 623 nm versus SDS concentration……………………...82
Figure 15. Emission intensity ratio at 623 nm for EtdBr between 0−2% of SDS……83
Figure 16. UV−Visible absorption spectra for EtdBr between 0−2% of TX-100……84
Figure 17. Fluorescence spectra for EtdBr between 0−2% of TX-100………………85
Figure 18. Emission intensity ratio at 628 nm for EtdBr between 0−2% of TX-100……………………………………………………………………………….85
Figure 19. Diagram of the interaction for EtdBr-TX-100 micelle…………………...87
Figure 20. Absorption maximum of n→pi* transition for EtdBr in SDS and TX-100 solution……………………………………………………………………………….88
Figure 21. Emission intensity ratio for EtdBr in SDS and TX-100 solution…………89
Figure 22. UV−Visible absorption spectra for EtdBr in 0% and 2% of CTAB……...90
Figure 23. Fluorescence spectra for EtdBr in 0% and 2% of CTAB…………………90
Figure 24. UV−Visible absorption spectra of EtdBr in 0% (H2O), 0.1% and 2% SDS aqueous solution and two organic solvent DCM and DMSO………………......92
Figure 25. Resonance structures of ethidium cation…………………………………94
Figure 26. Emission intensity at 615 nm and absorption maximum of n→pi* transition for EtdBr between pH 0−14 in NaPi buffer solution……………………...95
Figure 27. Emission intensity at 610 nm and absorption maximum of n→pi* transition for EtdBr between pH 1−10 in CH3CN……………....................................95
Figure 28. UV−Visible absorption spectrum of ethidium cation with predicted TD-DFT transition……………………………………………………………………97
Figure 29. UV−Visible absorption spectrum of deprotonated ethidium cation (Etd-RH) with predicted TD-DFT transition…………………………………………97
Figure 30. UV−Visible absorption spectrum of deprotonated ethidium cation (Etd-LH) with predicted TD-DFT transition…………………………………………98
Figure 31. Luminescence decay of EtdBr in 0.1% of SDS…………………………..99
Figure 32. Emission intensity ratio at 623 nm and fluorescence lifetime ratio at 615 nm for EtdBr below 0.1% of SDS……………………………………………...100
Figure 33. Emission intensity ratio at 623 nm and fluorescence lifetime ratio at 615 nm for EtdBr below 1% of SDS………………………………………………..101
Figure 34. UV−Visible absorption spectra for EtdBr in 0%, 0.1% and 1% of sodium sulfate………………………………………………………………………102
Figure 35. Fluorescence spectra for EtdBr in 0%, 0.1% and 1% of sodium sulfate……………………………………………………………………………….103
Figure 36. UV−Visible absorption spectra for EtdBr in 0%, 0.1% and 1% of sodium methyl sulfate………………………………………………………………103
Figure 37. Fluorescence spectra for EtdBr in 0%, 0.1% and 1% of sodium methyl sulfate……………………………………………………………………………….104
Figure 38. UV−Visible absorption spectra for EtdBr in 0%, 0.1%, 0.5% and 1% of sodium hexyl sulfate……………………………………………………………..105
Figure 39. Fluorescence spectra for EtdBr in 0%, 0.1%, 0.5% and 1% of sodium hexyl sulfate………………………………………………………………………...105
Figure 40. UV−Visible absorption spectra for EtdBr in 0%, 0.1%, 0.5% and 1% of sodium octyl sulfate……………………………………………………………...106
Figure 41. Fluorescence spectra for EtdBr in 0%, 0.1%, 0.5% and 1% of sodium octyl sulfate…………………………………………………………………………106
Figure 42. UV−Visible absorption spectra for EtdBr between 0−0.1% of sodium tetradecyl sulfate…………………………………………………………………….108
Figure 43. Fluorescence spectra for EtdBr between 0−0.1% of sodium tetradecyl sulfate……………………………………………………………………………….109
Figure 44. Emission intensity ratio at 615 nm for EtdBr between 0−0.1% of sodium tetradecyl sulfate……………………………………………………………110
Figure 45. Calculating the binding constant from the fitting curve for the plot of EtdBr emission intensity at 615 nm versus sodium tetradecyl sulfate concentration………………………………………………………………………..110
Figure 46. Absorption maximum of n→pi* transition and emission intensity ratio at 623 nm for EtdBr between 0−2% of SDS………………………………………..114
Figure 47. Absorption maximum of n→pi* transition and emission intensity ratio at 628 nm for EtdBr between 0−2% of TX-100…………………………………….114


Figure S1. Phosphorescence spectra for Ru(bpy)2dppz2+ between 0−2% of TX-100……………………………………………………………………………...120
Figure S2. Phosphorescence spectra for Ru(bpy)2dppz2+ between 0−2% of CTAB………………………………………………………………………………..120
Figure S3. Fluorescence spectra for diluted EtdBr between 0−2% of SDS………...121
Figure S4. Emission intensity ratio at 620 nm for diluted EtdBr between 0−2% of SDS………………………………………………………………………………….122
Figure S5. UV−Visible absorption spectra for EtdBr in various pH values of NaPi buffer solution………………………………………………………………………122
Figure S6. Fluorescence spectra for EtdBr in various pH values of NaPi buffer solution……………………………………………………………………………...123
Figure S7. UV−Visible absorption spectra for EtdBr in basic condition of CH3CN……………………………………………………………………………...124
Figure S8. Fluorescence spectra for EtdBr in basic condition of CH3CN………….124
Figure S9. UV−Visible absorption spectra for EtdBr in acidic condition of CH3CN……………………………………………………………………………...125
Figure S10. Fluorescence spectra for EtdBr in acidic condition of CH3CN………..125
Figure S11. Luminescence decay of EtdBr in 0.001% of SDS……………………..126
Figure S12. Luminescence decay of EtdBr in 0.005% of SDS……………………..126
Figure S13. Luminescence decay of EtdBr in 0.01% of SDS………………………127
Figure S14. Luminescence decay of EtdBr in 0.05% of SDS………………………127
Figure S15. Luminescence decay of EtdBr in 0.2% of SDS………………………..128
Figure S16. Luminescence decay of EtdBr in 1% of SDS………………………….128
Figure S17. Luminescence decay of EtdBr in pure water…………………………..129


Chapter 3
Figure 1. GC−MS chromatogram of seven essential oils (linear temperature gradient)…………………………………………………………………………….139
Figure 2. GC−MS chromatogram for tea tree essential oil…………………………140
Figure 3. GC−MS chromatogram for rose geranium essential oil………………….141
Figure 4. GC−MS chromatogram of seven essential oils (step temperature gradient)…………………………………………………………………………….141
Figure 5. Growth curves of E. coli in LB medium in the absence and presence of patchouli essential oil……………………………………………………………….150
Figure 6. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of seven essential oils after 24 hours of incubation…………………………………………..152


Figure S1. GC−MS chromatogram for lemon verbena essential oil……………......158
Figure S2. GC−MS chromatogram for sweet marjoram essential oil………………159
Figure S3. GC−MS chromatogram for clove basil essential oil……………………159
Figure S4. GC−MS chromatogram for patchouli essential oil……………………...160
Figure S5. GC−MS chromatogram for rosemary essential oil……………………...160
Figure S6. The regression relationship between the concentration of geraniol and its integrated area of abundance in the GC−MS chromatogram……………………161
Figure S7. The regression relationship between the concentration of 1,8-cineole and its integrated area of abundance in the GC−MS chromatogram……………….161
Figure S8. The regression relationship between the concentration of beta-caryophyllene and its integrated area of abundance in the GC−MS chromatogram……………………………………………………………………….162
Figure S9. Growth curves of E. coli in LB medium in the absence and presence of clove basil essential oil…………………………………………………………..162
Figure S10. Growth curves of E. coli in LB medium in the absence and presence of sweet marjoram essential oil……………………………………………………..163
Figure S11. Growth curves of E. coli in LB medium in the absence and presence of lemon verbena essential oil………………………………………………………163
Figure S12. Growth curves of E. coli in LB medium in the absence and presence of tea tree essential oil………………………………………………………………164
Figure S13. Growth curves of E. coli in LB medium in the absence and presence of rosemary essential oil…………………………………………………………….164
Figure S14. Growth curves of E. coli in LB medium in the absence and presence of rose geranium essential oil……………………………………………………….165
Figure S15. Inhibitory effect of E. coli growth by 0.01%, 0.02%, 0.05% and 0.1% of patchouli essential oil after 24 hours of incubation……………………………...165
Figure S16. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of clove basil essential oil after 24 hours of incubation……………………………….166
Figure S17. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of sweet marjoram essential oil after 24 hours of incubation………………………….166
Figure S18. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of lemon verbena essential oil after 24 hours of incubation…………………………...167
Figure S19. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of tea tree essential oil after 24 hours of incubation……………………………………….167
Figure S20. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of rosemary essential oil after 24 hours of incubation…………………………………168
Figure S21. Inhibitory effect of E. coli growth by 0.01%, 0.05% and 0.1% of rose geranium essential oil after 24 hours of incubation……………………………168


List of Tables
Chapter 1
Table 1. Absorption and emission maximum of ruthenium model compounds in 50 mM NaPi buffer solution………………………………………………………….19
Table 2. Photophysical properties of ruthenium model compounds in 50 mM NaPi buffer solution………………………………………………………………………..21
Table 3. Quenching efficiency between ruthenium model compounds and Rua63+….24
Table 4. Driving forces of the bimolecular quenching reaction between ruthenium model compounds and Rua63+………………………………………………………..25
Table 5. Bimolecular quenching reaction between ruthenium model compounds and Rua63+…………………………………………………………………………….31
Table 6. Bimolecular quenching reaction between ruthenium modified Fe3+-cyt c and Rua63+…………………………………………………………………………….36
Table 7. Bimolecular quenching reaction between ruthenium modified Fe2+-cyt c and Rua63+…………………………………………………………………………….38
Table 8. Intramolecular electron transfer rate constants for the ruthenium modified Fe2+-cyt c……………………………………………………………………………..42
Table 9. Intramolecular electron transfer within the ruthenium modified Fe2+-cyt c……………………………………………………………………………..46


Table S1. Supplement for the bimolecular quenching reaction between ruthenium modified Fe3+-cyt c and Rua63+………………………………………………………58
Table S2. Supplement for the bimolecular quenching reaction between ruthenium modified Fe2+-cyt c and Rua63+………………………………………………………58


Chapter 2
Table 1. Absorption and emission maximums of EtdBr in H2O, DCM and DMSO with the specific physical properties of solvents……………………………………..92
Table 2. Fluorescence lifetime and normalized emission intensity of EtdBr in various concentrations of SDS……………………………………………………...100


Chapter 3
Table 1. Volatile components of the seven essential oils and their relative abundance…………………………………………………………………………...143
Table 2. The major components and their structures of the seven essential oils……147
Table 3. Comparison for major components with various origins of tea tree essential oils………………………………………………………………………...148


List of Schemes
Chapter 1
Scheme 1. Mechanism of the direct photoinduced electron transfer for Ru2+(bpy)2(dcbpy)-Lys-Fe3+-cyt c……………………………………………………..8
Scheme 2. Mechanism of the flash-quench method for Ru2+(bpy)2(im)(His33)-Fe2+-cyt c……………………………………………………...9
Scheme 3. Synthetic scheme of ruthenium model compounds………………………11


Chapter 2
Scheme 1. Assay of estimating for the concentration of SDS in aqueous solution…112
                                

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