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研究生：	陳亞倫 Chen, Ya-Lun
論文名稱：	銥(III)環金屬錯合物(1)化學感測器研究與應用(2) X-ray分析 The study and application of Ir(III) complex (1) in chemosensors (2) X-ray analysis
指導教授：	黃福永 Huang, Fu-Yung
學位類別：	碩士 Master
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2011
畢業學年度：	99
語文別：	英文
論文頁數：	117
中文關鍵詞：	銥金屬、感測器
外文關鍵詞：	iridium, chemosensor
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在本研究中，我們合成了兩種具有偵測重金屬功能的銥金屬(III)錯合物 : [Ir(pba)2pbi]與[Ir(ppm)2pbi]。配位基pbi上之氮原子所具有的孤電子的存在，是使之能夠偵測到Hg2+、Ce3+、Cr3+以及Fe3+等金屬離子的原因。氮原子與這些金屬離子之間的作用力，可從吸收光譜與放光光譜的變化得知。從吸收光譜中我們可以看到等吸收點的存在，而從放光光譜中我們也發現與金屬離子錯合前後，錯合物的放光強度也會有不同程度的改變。
為了確認錯合物的醛基以及氫氧基的部位確實沒有與金屬陽離子結合的能力,我們合成[Ir(pba)2bpy](PF6)與[Ir(ppm)2bpy](PF6)以作為對照。即使[Ir(pba)2bpy](PF6)的放光強度比起[Ir(pba)2pbi]還要強很多，但是Ir(pba)2bpy](PF6)卻沒有表現出任何能夠偵測金屬的能力。
其次我們利用X-RAY數據分析晶體的鍵長與鍵角,發現到與理論計算方法(DFT)分析結果不ㄧ樣，因此有必要再做進一步的探討。

In this studies, we had successfully synthesized two Ir(III)-complexes, [Ir(pba)2pbi] and [(ppm)2pbi], in which the moiety of pba is 4-(pyridin-2-yl)benzaldehyde, the pbi moiety is 2-(pyridine-2-yl)-H-benzo[d]imidazole, and the ppm mpiety is (4-( pyridine-2-yl)phenyl)methanol. Both complexes are capable of chelating with heavy metal ion and concomitantly appear different color. The lone-paired electrons on the nitrogen atom of the pbi ligand was responsible for chelating with the following metal ions: Hg2+ , Ce3+, Cr3+ and Fe3+ . The interactions between Nitrogen of (pbi) and various metal ions interaction was found based on the data of UV-VIS and luminescence spectra .

In order to examine why the carbonyl group of pba or the hydroxyl oxygen atoms is unable to semi-coordinating with metal ion, [Ir(pba)2bpy](PF6) and [Ir(ppm)2bpy](PF6) had been synthesized and been used as a comparison . The carbonyl oxygen of [Ir(pba)2bpy](PF6) failed to chelating the metal ions, even the luminescence intensities were found much higher than that of [Ir(pba)2pbi] .

We further employed X –RAY crystallographic data to analysis the bond length and bond angle of the complexes, and found that the data obtained from the crystallography is different from that obtained from theory calculations. It is thus interesting to study further.

Table of Contents

Abstract………………………………………………………………………………... I
Acknowledgement……………………………………………………………………III
List of Charts…………………………………………………………………………VII
List of Tables…………………………………………………………………………VII
List of Figures...........................VII


Chapter 1.  Introduction………………………………………………………….1
Chapter 2.  Research background………………………………………………3
   I) Review on Crown ether chemical sensor……………………………………… 3
      A. General crown ethers in use…………………………………………........3
       B. Remarkable Developments………………………………………………..4
                 B-1 Complexing agents for divalent cations……………………4
                 B-2 Crown-based ionsensors……………………………………4
                 B-3 Fluorescence signaling……………………………………..5
                 B-4 sense ion pairs……………………………………………...6
                 B-5 Sensing by emission technique…………………………….6
   (II) Review on Anion Sensing……………………………………………………..7
        A.  Binding Site−Signaling Subunit Approach……………………………8
       B. Displacement Approach…………………………………………………8
        C. Chemodosimeter Approach……………………………………………...9
(III) Review on Fluorescent Sensors Based on Ruthenium and Iridium, 
       Complexes……………………………………………………………………9
         A. Containing Ru(bipy)32+ and other Units………………………………10
        B. Ir(tpy)23+ and other ligands Units…………………………………………..12
    (Ⅳ) Research and Motivation………………………………………………….13 
Chapter 3. Experimental Section…………………………………………..18
    3-1 Instrumentation……………………………………………………………18
    3-2 Materials…………………………………………………………………...20   
    3-3 Synthesize………………………………………………………………….21  
        3-3-1 Synthesis of 2-(2-pyridyl)benzimidazole………………………….21    
        3-5-2 Synthesis of [Ir2 (pba) 4Cl2]…………………………………………22     
        3-5-3 Sythesis of [Ir(pba)2(bpy)](PF6)…………………………………….24     
        3-5-4 Synthesis of [Ir(pba)2(pbi)]………………………………………...27         
        3-5-5 synthesis of [Ir(ppm)2(bpy)](PF6)…………………………………29   
        3-5-6 synthesis of [Ir(ppm)2(pbi)]……………………………………….32 
Chapter 4 . Results and Discussion………………………………………….35
4-A  Crystallographic characterization and analysis…………………………36
4-A-1 Ir2pba4Cl2...........................................................................................36
4-A-2 Complex [Irpba2bpy]PF6,[Irppm2bpy]PF6,Irpba2pbi..........................41
4-A-3 Ir(ppm)2bpy…………………………………………………………42
4-B  Chemosensor and Photophysics………………………………………...48
4-B-1 Complex 3: invalidity of site A for chelation……………………….50
4-B-2 Complex 2: Site B supplied by Ir(pba)2 (pbi)……………………...51  
4-B-3 Complex 5: confirmation of site B in binding metal ions………….52
    4-B-4 Complex 4: chemical sensor suitable for detection in aqueous  systems………………………………………………...53
Chapter 5   Conclusion and extension work……………………………54
Reference…………………………………………………………………………..62
Appendix…………………………………………………………………………..66


List of charts
Chart 1.  The iridium (III) diimine complex [Ir(N-C)2(N-N)](PF6).....13
Chart 2.  iridium complex sensor cation and anion……………………16

List of Table
Table  4A-1. Selective bond-lengths of complex Ir2pba4Cl2…36
Table  4A-2. Bite angles of complex Ir Ir2pba4Cl2…………………….37
Table  4A-3. Crystallographic acquisition parameters for Ir2pba4Cl2…38
Table  4A-4. Crystallographic acquisition parameters for Complexes (2), (3), (5)...39 
Table  4A-5. Selective bond-lengths and angles of complexes (2), (3) and (5)................41

List of figures

Figure 1-1. Two possible sites, A and B, provided by Ir(pba)2bpi cationic complex...….2
Figure 2-1. Cyclo-oligomers of ethylene oxide, from dioxane 18-crown-6………4
Figure 2-2 Crown-based ionsensors………………………………………………...…4
Figure 2-3 De Silva’s anthracenylmethyl lariat ether for fluorescence signaling……..5
Figure 2-4 Luminescent sensor for ion pairs.………………..5
Figure 2-5 Luminescent sensor for divalent cations…………….6
Figure 2-6 Anion chemosensors based on the binding site-signaling subunit approach ………..7
Figure 2-7 Anion chemosensors based on the displacement approach……………………..….…8
Figure 3-1 NMR spectrum of ligand pbi……………………………………………..22
Figure 3-2 NMR spectrum of [Ir2(pba)4Cl2] …………………………………………23
Figure 3-3 IR spectrum of [Ir2(pba)4Cl2]................24
Figure 3-4 NMR spectrum of [Ir(pba)2bpy](PF6)……………….25
Figure 3-5 IR spectrum of [Ir(pba)2bpy](PF6) ………………….26
Figure 3-6 MASS spectrum of [Ir(pba)2bpy](PF6)……………...26
Figure 3-7 NMR spectrum of [Ir(pba)2pbi]…………………………………………..28
Figure 3-8 IR spectrum of [Ir(pba)2pbi]………………………………………...28
Figure 3-9 MASS spectrum of [Ir(pba)2pbi]…………………………………....29
Figure 3-10 NMR spectrum of [Ir(ppm)2(bpy)](PF6)………………...30
Figure 3-11 IR spectrum of [Ir(ppm)2(bpy)](PF6) …………………...31
Figure 3-12 MASS spectrum of [Ir(ppm)2(bpy)](PF6)………………….31
Figure 3-13 NMR spectrum of [Ir(ppm)2(pbi)] …………………………...33
Figure 3-14 IR spectrum of [Ir(ppm)2(pbi)]……………………………….…33
Figure 3-15 MASS spectrum of [Ir(ppm)2(pbi)]………………………….….34
Figure 4A-1 Structural representation of Ir(III) complexes under this study……......35
Figure 4A-2 H-Bonding network……………………………………………..……...42
Figure 4A-3 PF6-centered framework……………………………………………….44
Figure 4A-4 Numbering of atoms in Ir(ppm)2bpy……………………………44
Figure 4A-5 bpy-centered framework………………………………………………..45
Figure 4A-6 bpy-centered framework bond lengt…………………………….46
Figure 4A-7 Enlargement of two N(bpy)-Ir-C(ppm) angles……….46
Figure 4B-1 Structural representation of Ir(III) complexes under this study…….….48
Figure 4B-2 Possible sites provided by (A)Ir(pba)2pbi and (B)Ir(pba)2bpy for chelating metal ions………………………………………. 49
Figure 4B-3 Response of luminescence data of [Ir(pba)2(bpy)](PF6) in the presence of metal ions at different concentration…………….50
Figure 4B-4 Response of luminescence data of [Ir(pba)2(pbi)] in the presence of metal ions at different concentration……………………………….51
Figure 4B-5 Response of luminescence data of [Ir(ppm)2(bpy)](PF6) in the presence of metal ions at different concentration………………………………....52
Figure 4B-6 Response of luminescence data of [Ir(ppm)2(pbi)] in the presence of metal ions at different concentration…………………………………....53
Figure 5-1  (A) absorption spectrum of [Rh(ppy)2(bpym)][PF6] (B) emission polarization spectrum of [Rh(ppy)2(bpym)][PF6]……………..……....57
Figure 5-2  (A) emission spectrum and (B) emission polarization spectrum of [Rh(ppy)2(bpym)][PF6]……………………..58
Figure 5-3  Emission spectra of [Rh(ppy)2(bpym)][PF6] ……….59
Figure 5-4  Cyclic voltammogram of 1.0 mM [Rh(ppy)2(bpym)][PF6]…………….60
Figure 5-5  Cyclic voltammogram of 1.0 mM [Rh(ppy)2(bpym)][PF6]…………….61
Figure.A-1  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Ag+ concentration……66
Figure.A-2  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) i upon addition of different K+ concentration …...67
Figure.A-3  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Na+ concentration …...68
Figure.A-4  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Ba2+ concentration …..69
Figure.A-5  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Ca2+ concentration…...70
Figure.A-6  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Cd2+ concentration…...71 
Figure.A-7  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Co2+ concentration…...72 
Figure.A-8  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Hg2+ concentration…..73 
Figure.A-9  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Ni2+ concentration…...74 
Figure.A-10  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Zn2+ concentration…...75 
Figure.A-11  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Ce3+ concentration…...76 
Figure.A-12  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Cr3+ concentration…...77 
Figure.A-13  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(bpy)](PF6) upon addition of different Fe3+ concentration…...78 
Figure.A-14  Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Ag+ concentration………….79 
Figure.A-15 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different K+ concentration…………...80 
Figure.A-16 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Na+ concentration………….81
Figure.A-17 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Ba2+ concentration…………82 
Figure.A-18 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Ca2+ concentration…………83

Figure.A-19 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Cd2+ concentration…………84 
Figure.A-20 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Co2+ concentration…………85 
Figure.A-21 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Hg2+ concentration…………86 
Figure.A-22 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Ni2+ concentration………….87
Figure.A-23 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Zn2+ concentration…………88
Figure.A-24Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Ce3+ concentration…………89
Figure.A-25 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Cr3+ concentration………….90
Figure.A-26 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(pba)2(pbi)] upon addition of different Fe3+ concentration………….91
Figure.A-27 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Ag+ concentration…...92
Figure.A-28 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different K+ concentration……93
Figure.A-29 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Na+ concentration…...94
Figure.A-30 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Ba2+ concentration…..95
Figure.A-31 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Ca2+ concentration…..96
Figure.A-32 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Cd2+ concentration….97
Figure.A-33 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Co2+ concentration….98
Figure.A-34 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Hg2+ concentration….99
Figure.A-35 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Ni2+ concentration…100
Figure.A-36 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Zn2+ concentration…101
Figure.A-37 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Ce3+ concentration…102
Figure.A-38 Photoluminescence(A) and Absorption spectra (B) changes of  [Ir(ppm)2(bpy)](PF6) upon addition of different Cr3+ concentration…103 
Figure.A-39 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(bpy)](PF6) upon addition of different Fe3+ concentration…104 
Figure.A-40 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Ag+ concentration………..105 
Figure.A-41 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different K+ concentration…………106
Figure.A-42 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Na+ concentration………..107 
Figure.A-43 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Ba2+ concentration……….108 
Figure.A-44 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Ca2+ concentration……….109 
Figure.A-45 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Cd2+ concentration……….110 
Figure.A-46 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Co2+ concentration……….111 
Figure.A-47 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Hg2+ concentration…….....112 
Figure.A-48 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Ni2+ concentration…….....113
Figure.A-49 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Zn2+ concentration……….114
Figure.A-50 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Ce3+ concentration……….115
Figure.A-51 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Cr3+ concentration……….116
Figure.A-52 Photoluminescence(A) and Absorption spectra (B) changes of [Ir(ppm)2(pbi)] upon addition of different Fe3+ concentration……….117

                                    

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