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研究生:林家弘
研究生(外文):Chia-Hung Lin
論文名稱:合成能用肉眼辨識陰離子之感測器
論文名稱(外文):Development of colorimetric chemosensors for anions
指導教授:顏耀平
指導教授(外文):Yao-Pin Yen
學位類別:碩士
校院名稱:靜宜大學
系所名稱:應用化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2006/07/
畢業學年度:94
語文別:中文
論文頁數:251
中文關鍵詞:發色團陰離子感測器
外文關鍵詞:chemosensordicarboxylate anion
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開發三個新的colorimetric chemosensor經由實驗整理結果發現,化合物13在與無機陰離子F-,Cl-,Br-,I-,OH-,AcO-,NO3-,HSO4-結合時發現只有F-與OH-離子與13結合產生顏色變化,由藍色變為綠色。而化合物13與dicarboxylate anions malonate,succinate,glutarate,adipate
,結合時發現只有與malonate結合產生顏色變化,由藍色變為綠色。13與dicarboxylate anions (cis/trans)及(ortho-/meta-/para-)結合時發現只有與maleate(cis)及o-phthalate產生顏色變化,由藍色變為綠色。
化合物14與所有測定離子結合時發現到只有與fumarate(trans)結合產生顏色變化,由紫色變為黃色。
化合物15與所有測定離子結合時發現到只有與OH-產生顏色變化,由藍色變為綠色。
Through this experiment, I develop three new colorimetric chemosensor, compound 13 with inorganic anion F-, Cl-, Br-, I-, OH-, AcO-, NO3-, HSO4- discovered only F- and the OH- products color change, becomes the green by the blue color. As well as compound 13 with the malonate, maleate (cis) and o-phthalate. Compound 14 makes color change, the color yellow by purple, with fumarate (trans) in all determined ions.Compound 15 products color change, the color green by blue, with OH- in all determined ions.
摘要………………………………………………………….1
壹、緒論…………………………………………………….3
貳、結果與討論…………………………………………….8
參、結論…………………………………………………..209
肆、實驗藥品與儀器……………………………………..212
伍、實驗步驟與數據…………………………………......215
陸、參考文獻……………………………………………...244
柒、附錄…………………………………………………...245

圖目錄
Fig.1 Effect of anions (as (C4H9)4N+ salt) on color changes of 1 in
DMSO……………………………………………………………...6

Fig.2 Family of spectra taken in the course of the titration of a 5×10-5 M DMSO solution in 13 with a standard solution of malonate at 25℃titration profiles(insert) indicate the formation of a 1:1 complex..20
Fig.3 compound 13 (5×10-5M)與malonate作用後顏色改變…………..21
Fig.4 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of succinate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..25
Fig.5 compound 13 (5×10-5M)與succinate作用後顏色的改變………..26
Fig.6 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of glutarate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..30
Fig.7 compound 13 (5×10-5M)與glutarate作用後顏色的改變……….31
Fig.8 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of adipate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..35
Fig.9 compound 13 (5×10-5M)與adipate作用後顏色的改變…………36
Fig.10 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of maleate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..40
Fig.11 compound 13 (5×10-5M)與maleate作用後顏色的改變………..41
Fig.12 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of fumarate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..45
Fig.13 compound 13 (5×10-5M)與fumarate作用後顏色的改變……...46
Fig.14 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of o-phthalate at 25
℃ titration profiles(insert) indicate the formation of a 1:1 complex
……………………………………………………………………50
Fig.15 compound 13 (5×10-5M)與o-phthalate作用後顏色的改變……51
Fig.16 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of m-phthalate at
25℃ titration profiles(insert) indicate the formation of a 1:1
complex…………………………………………………………55
Fig.17 compound 13 (5×10-5M)與m-phthalate作用後顏色的改變…..56
Fig.18 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of p-phthalate at 25
℃ titration profiles(insert) indicate the formation of a 1:1 complex
……………………………………………………………………60
Fig.19 compound 13 (5×10-5M)與p-phthalate作用後顏色的改變……61
Fig.20 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+OH- at 25℃
……………………………………………………………………63
Fig.21 compound 13 (5×10-5M)與TBA+OH-作用後顏色的改變……..63
Fig.22 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+F- at 25℃
…………………………………………………………………..65
Fig.23 compound 13 (5×10-5M)與TBA+F-作用後顏色的改變……….65
Fig.24 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+Cl- at 25
℃…………………………………………………………………67
Fig.25 compound 13 (5×10-5M)與TBA+Cl-作用後顏色的改變……….67
Fig.26 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+Br- at 25
℃…………………………………………………………………69
Fig.27 compound 13 (5×10-5M)與TBA+Br-作用後顏色的改變………69
Fig.28 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+I- at 25
℃………………………………………………...........................71
Fig.29 compound 13 (5×10-5M)與TBA+I-作用後顏色的改變………..71
Fig.30 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+NO3- at 25
℃……………………………………………….........................73
Fig.31 compound 13 (5×10-5M)與TBA+NO3-作用後顏色的改變……73
Fig.32 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+AcO- at 25
℃………………………………...................................................75
Fig.33 compound 13 (5×10-5M)與TBA+AcO-作用後顏色的改變…….75
Fig.34 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 13 with a standard solution of TBA+HSO4- at
25℃………………………………………………………………77
Fig.35 compound 13 (5×10-5M)與TBA+HSO4-作用後顏色的改變…...77
Fig.36 UV-vis change of 13 operated in DMSO (5×10-5M) after the
addidion of 2 equiv.of anion…………………………………….78
Fig.37 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of malonate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..82
Fig.38 compound 14 (5×10-5M)與malonate作用後顏色的改變……..83
Fig.39 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of succinate at 25℃
titration profiles(insert) indicate the formation of a 1:1complex...87
Fig. 40 compound 14 (5×10-5M)與succinate作用後顏色的改變……..88
Fig. 41 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of glutarate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..92
Fig. 42 compound 14 (5×10-5M)與glutarate作用後顏色的改變……..93
Fig. 43 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of adipate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex..97
Fig. 44 compound 14 (5×10-5M)與adipate作用後顏色的改變……….98
Fig. 45 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of maleate at 25℃
titration profiles(insert) indicate the formation of a 1:1complex...102
Fig. 46 compound 14 (5×10-5M)與maleate作用後顏色的改變……103
Fig. 47 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of fumarate at 25℃
titration profiles(insert) indicate the formation of a 1:1complex.107
Fig. 48 compound 14 (5×10-5M)與fumarate作用後顏色的改變…108
Fig. 49 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of o-phthalate at 25
℃titration profiles(insert) indicate the formation of a 1:1 complex
…………………………………………………………………112
Fig. 50 compound 14 (5×10-5M)與o-phthalate作用後顏色的改變…113
Fig. 51 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of m-phthalate at
25℃ titration profiles(insert) indicate the formation of a 1:1
complex……………………………………………………….117
Fig. 52 compound 14 (5×10-5M)與m-phthalate作用後顏色的改變…118
Fig. 53 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of p-phthalate at 25
℃titration profiles(insert) indicate the formation of a 1:1
complex……………………………………………………….122
Fig. 54 compound 14 (5×10-5M)與p-phthalate作用後顏色的改變…123
Fig. 55 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+OH- at 25
℃……………………………………………………………....125
Fig. 56 compound 14 (5×10-5M)與TBA+OH-作用後顏色的改變……125
Fig. 57 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+F- at 25
℃………………………………………………………………127
Fig. 58 compound 14 (5×10-5M)與TBA+F-作用後顏色的改變………127
Fig. 59 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+Cl- at 25
℃………………………………………………………………129
Fig. 60 compound 14 (5×10-5M)與TBA+Cl-作用後顏色的改變…….129
Fig. 61 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+Br- at 25
℃……………………………………………………………....131
Fig. 62 compound 14 (5×10-5M)與TBA+Br-作用後顏色的改變……..131
Fig. 63 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+I- at 25
℃………………………………………………………………133
Fig. 64 compound 14 (5×10-5M)與TBA+I-作用後顏色的改變………133
Fig. 65 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+NO3- at 25
℃……………………………………………………………....135
Fig. 66 compound 14 (5×10-5M)與TBA+NO3-作用後顏色的改變…..135
Fig. 67 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+AcO- at 25
℃………………………………………………………………137
Fig. 68 compound 14 (5×10-5M)與TBA+AcO-作用後顏色的改變…...137
Fig. 69 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 14 with a standard solution of TBA+HSO4- at
25℃……………………………………………………………139
Fig. 70 compound 14 (5×10-5M)與TBA+HSO4-作用後顏色的改變…139
Fig. 71 UV-vis changes of 14 operated in DMSO (5×10-5 M) after the
addition of 2 equiv. of anion…………………………………..140
Fig. 72 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of malonate at 25
℃ titration profiles(insert) indicate the formation of a 1:1
complex………………………………………………………144
Fig. 73 compound 15 (5×10-5M)與malonate作用後顏色的改變……145
Fig. 74 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of succinate at 25
℃ titration profiles(insert) indicate the formation of a 1:1
complex………………………………………………………..149
Fig. 75 compound 15 (5×10-5M)與succinate作用後顏色的改變……150
Fig. 76 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of glutarate at 25℃
titration profiles(insert) indicate the formation of a 1:1complex
…………………………………………………………………154
Fig. 77 compound 15 (5×10-5M)與glutarate作用後顏色的改變…….155
Fig. 78 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of adipate at 25℃
titration profiles(insert) indicate the formation of a 1:1 complex
…………………………………………………………………159
Fig. 79 compound 15 (5×10-5M)與adipate作用後顏色的改變………160
Fig. 80 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of maleate at 25℃
titration profiles(insert) indicate the formation of a 1:1
complex……………………………………………………….164
Fig. 81 compound 15 (5×10-5M)與maleate作用後顏色的改變…….165
Fig. 82 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of fumarate at 25℃
titration profiles(insert) indicate the formation of a 1:1
complex………………………………………………………169
Fig. 83 compound 15 (5×10-5M)與fumarate作用後顏色的改變…..170
Fig. 84 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of o-phthalate at 25
℃ titration profiles(insert) indicate the formation of a 1:1
complex…………………………………………………………174
Fig. 85 compound 15 (5×10-5M)與o-phthalate作用後顏色的改變…175
Fig. 86 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of m-phthalate at
25℃ titration profiles(insert) indicate the formation of a 1:1
complex………………………………………………………..179
Fig. 87 compound 15 (5×10-5M)與m-phthalate作用後顏色的改變….180
Fig. 88 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of p-phthalate at 25
℃ titration profiles(insert) indicate the formation of a 1:1
complex……………………………………………………....184
Fig. 89 compound 15 (5×10-5M)與p-phthalate作用後顏色的改變…185
Fig. 90 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of TBA+OH- at 25
℃ titration profiles(insert) indicate the formation of a 1:1
complex………………………………………………………..189
Fig. 91 compound 15 (5×10-5M)與TBA+OH- 作用後顏色的改變….190
Fig. 92 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of TBA+F- at 25
℃………………………………………………………………192
Fig. 93 compound 15 (5×10-5M)與TBA+F- 作用後顏色的改變……..192
Fig. 94 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of TBA+Cl- at 25
℃………………………………………………………………194
Fig.95 compound 15 (5×10-5M)與TBA+Cl- 作用後顏色的改變……194
Fig. 96 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of TBA+Br- at 25
℃……………………………………………………………...196
Fig. 97 compound 15 (5×10-5M)與TBA+Br- 作用後顏色的改變…..196
Fig. 98 Family of spectra taken in the course of the titration of a 5×10-5 M
DMSO solution in 15 with a standard solution of TBA+I- at 25
℃………………………………………………………………198
Fig. 99 compound 15 (5×10-5M)與TBA+I- 作用後顏色的改變……...198
Fig. 100 Family of spectra taken in the course of the titration of a 5×10-5
M DMSO solution in 15 with a standard solution of TBA+NO3-
at 25℃………………………………………………………..200
Fig. 101 compound 15 (5×10-5M)與TBA+NO3- 作用後顏色的改變..200
Fig. 102 Family of spectra taken in the course of the titration of a 5×10-5
M DMSO solution in 15 with a standard solution of TBA+AcO-
at 25℃……………………………………………………….202
Fig. 103 compound 15 (5×10-5M)與TBA+AcO- 作用後顏色的改變202
Fig. 104 Family of spectra taken in the course of the titration of a 5×10-5
M DMSO solution in 15 with a standard solution of TBA+HSO4-
at 25℃………………………………………………………204
Fig. 105 compound 15 (5×10-5M)與TBA+HSO4- 作用後顏色的改變204
Fig. 106 UV-vis changes of 15 operated in DMSO (5×10-5 M) after the
addition of 2 equiv. of anion………………………………….205

Fig. 107 UV-vis changes of 15 operated in DMSO (5×10-5 M) after the
addition of 2 equiv. of anion………………………………….206

Fig. 108 Effect of anions (as (C4H9)4N+ salt) on color changes of 15 in
DMSO………………………………………………………...207

Fig. 109 Possible binding model of 14 with fumarate anion…………..211

Fig. 110 1H NMR plot of 1,4-bis(p-trifluoromethylphenylthiourelyene-
ethene-amino)anthraquinone…………………………………218

Fig. 111 13C NMR plot of 1,4-bis(p-trifluoromethylphenylthiourelyene-
ethene-amino)anthraquinone…………………………………219

Fig. 112 HRMS plot of 1,4-bis(p-trifluoromethylphenylthiourelyene-
ethene-amino)anthraquinone…………………………………220

Fig. 113 NOESY plot of 1,4-bis(p-trifluoromethylphenylthiourelyene-
ethene-amino)anthraquinone………………………………....221

Fig. 114 COSY plot of 1,4-bis(p-trifluoromethylphenylthiourelyene-
ethene-amino)anthraquinone…………………………………222

Fig. 115 UV plot of 1,4-bis(p-trifluoromethylphenylthiourelyene-
ethene-amino)anthraquinone…………………………………223

Fig. 116 1H NMR plot of 1-{2-[4-(2-Amino-ethylamino)-9,10-dioxo-
9,10-dihydro-anthracen-1-ylamino]-ethyl}-3-(4-nitro-
naphthalen-1-yl)-thiourea…………………………………….225
Fig. 117 1H NMR plot of 1-(p-nitronaphthylthiourelyene-ethene-
amino)-4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...228

Fig. 118 13C NMR plot of 1-(p-nitronaphthylthiourelyene-ethene-
amino)-4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………..229

Fig. 119 HRMS plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-
4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...230

Fig. 120 NOESY plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-
4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...231

Fig. 121 COSY plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-4-
(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………..232

Fig. 122 UV plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-4-
(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...233

Fig 123: 1H NMR plot of 1-{2-[4-(2-Amino-ethylamino)-9,10-dioxo-
9,10-dihydro-anthracen-1-ylamino]-ethyl}-3-(4-nitro-phenyl)-
thiourea……………………………………………………….235

Fig. 124 1H NMR plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)
-4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...238

Fig. 125 13C NMR plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)
-4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...239

Fig. 126 HRMS plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-4-
(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...240

Fig. 127 NOESY plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-4
-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...241

Fig. 128 COSY plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-
4-(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………..242

Fig. 129 UV plot of 1-(p-nitronaphthylthiourelyene-ethene-amino)-4-
(p-trifluoromethylphenylthiourelyene-ethene-amino)
anthraquinone………………………………………………...243

























表目錄
Table.1 compound 13 (5×10-5M)與不同濃度的malonate作用後的
UV-VIS變化…………………………………………………18

Table.2 compound 13 (5×10-5M)與不同濃度的succinate作用後的
UV-VIS變化…………………………………………………23

Table.3 compound 13 (5×10-5M)與不同濃度的glutarate作用後的
UV-VIS變化…………………………………………………28

Table.4 compound 13 (5×10-5M)與不同濃度的adipate作用後的
UV-VIS……………………………………………………..33

Table.5 compound 13 (5×10-5M)與不同濃度的maleate作用後的
UV-VIS變化……………………………………………….38

Table. 6 compound 13 (5×10-5M)與不同濃度的fumarate作用後的
UV-VIS變化……………………………………………….43

Table. 7 compound 13 (5×10-5M)與不同濃度的o-phthalate作用後的
UV-VIS變化…………………………………………….....48

Table. 8 compound 13 (5×10-5M)與不同濃度的m-phthalate作用後的
UV-VIS變化……………………………………………….53

Table. 9 compound 13 (5×10-5M)與不同濃度的p-phthalate作用後的
UV-VIS變化….. …………………………………………..58

Table. 10 compound 14 (5×10-5M)與不同濃度的malonate作用後的
UV-VIS變化………………………………………………80

Table. 11 compound 14 (5×10-5M)與不同濃度的succinate作用後的
UV-VIS變化………………………………………………85

Table. 12 compound 14 (5×10-5M)與不同濃度的glutarate作用後的
UV-VIS變化………………………………………………90

Table. 13 compound 14 (5×10-5M)與不同濃度的adipate作用後的
UV-VIS變化………………………………………………95

Table. 14 compound 14 (5×10-5M)與不同濃度的maleate作用後的
UV-VIS變化……………………………………………...100

Table. 15 compound 14 (5×10-5M)與不同濃度的fumarate作用後的
UV-VIS變化……………………………………………105

Table. 16 compound 14 (5×10-5M)與不同濃度的o-phthalate作用後的
UV-VIS變化………………………………………………110

Table. 17 compound 14 (5×10-5M)與不同濃度的m-phthalate作用後的
UV-VIS變化………………………………………………115

Table. 18 compound 14 (5×10-5M)與不同濃度的p-phthalate作用後的
UV-VIS變化……………………………………………....120

Table. 19 compound 15 (5×10-5M)與不同濃度的malonate作用後的
UV-VIS變化………………………………………………142

Table. 20 compound 15 (5×10-5M)與不同濃度的succinate作用後的
UV-VIS變化………………………………………………147

Table. 21 compound 15 (5×10-5M)與不同濃度的glutarate作用後的
UV-VIS變化………………………………………………152

Table. 22 compound 15 (5×10-5M)與不同濃度的adipate作用後的
UV-VIS變化………………………………………………157

Table. 23 compound 15 (5×10-5M)與不同濃度的maleate作用後的
UV-VIS變化……………………………………………...162

Table. 24 compound 15 (5×10-5M)與不同濃度的fumarate作用後的
UV-VIS變化……………………………………………...167

Table. 25 compound 15 (5×10-5M)與不同濃度的o-phthalate作用後的
UV-VIS變化……………………………………………...172

Table. 26 compound 15 (5×10-5M)與不同濃度的m-phthalate作用後的
UV-VIS變化………………………………………………177

Table. 27 compound 15 (5×10-5M)與不同濃度的p-phthalate作用後的
UV-VIS變化………………………………………………182

Table. 28 compound 15 (5×10-5M)與不同濃度的TBA+OH- 作用後的
UV-VIS變化………………………………………………187

Table 29. Ka (M-1) of receptors 13 and 14 ,15 with dicarboxylate anions………………………………………………………208
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