本實驗使用具有巨大分子結構之樟腦磺酸(camphor sulfonic acid, CSA)與奎寧（ Quinine, Qu ）形成錯合 物達到抑制分子內轉動 (restricted intramolecular rotation, RIR) 進而顯現聚集誘導放光效應(aggregation-induced emission ，AIE)。不發光的鹼性奎寧與兩當量的樟腦磺酸質子化形成具備 AIE性質的離子錯合物 Qu(CSA)2。 第二部分則選用羅丹胼（Rhodamine hydrazide,RdH）作為具 AIE 性質的螢光基團，其用不具放光羅丹胼的與樟腦磺酸形成離子錯合物 RdH (CSA)3。 樟腦磺酸除了使羅丹胼開環使放光增強，同時也可以增強對離子錯合物 RdH (CSA)X的 RIR 效應。而具有離子鍵的 Qu(CSA)2和 RdH(CSA)3同時對於數個外部的刺激具有反應，因此可以作為金屬離子、 有機胺、pH 值的螢光感測器。而藉由 Qu(CSA)2 和 RdH (CSA)3 對天然蛋白質牛血清白蛋白（BSA）導致鏈展開，此可做為 BSA 的生物感測器。

Bulky camphorsulfonic acid (CSA) was used to complex with quinine (Qu) to impose the restricted intramolecular rotation (RIR) required for aggregation-induced emission (AIE) properties. After complexation with two equivalents of CSA, the
non-emissive quinine (Qu) base can be protonated to result in ionic complex Qu(CSA)2 with AIE properties. AIE-active rhodamine-based luminogen was prepared by complexation reaction between non-emissive rhodamine hydrazide (RdH) and bulky camphorsulfonic acid (CSA). Besides acting to open the spirolactam ring of RdH, CSA also imposes rotational restriction on the resultant ionic complex RdH(CSA)x. The ionic bonds of Qu(CSA)2 and RdH(CSA)3 are sensitive to several external stimuli and therefore, it is a luminescent sensor for metal ions, organic amines, pH value and the blood protein of bovine serum albumin (BSA); through the use of Qu(CSA)2 and RdH(CSA)3, the unfolding process of the BSA chains was evaluated.

Outline of contents
Chinese Abstract i
English Abstract ii
Outline of contents iii
List of Scheme vi
List of Figure vii

Chapter 1
Ionic Complex of Quinine and Camphor sulfonic Acid with Aggregation-Induce Emission
1. 1 Introduction 1
1. 1. 1 Fluorescence of quinine 1
1. 1. 2 Aggregation Induced Emission Phenomenon (AIE) 1
1. 1. 3 Fluorescence of protein 3
1. 1. 4 Ionic complex with Qu(CSA)2 4
1.2. Experimental sections 6
1.2.1 Materials 6
1.2.2 Instrumentations 7
1.3 Results and discussion 8
1.3.1 Emission behavior of Qu(CSA)x 9
1.3.2 Solution emission of Qu(CSA)x complexes 12
1.3.3 AIE property of Qu(CSA)2 13
1.3.4 NMR spectrum analysis 14
1.3.5 Emission variations at different pHs 17
1.3.6 Metal ions-driven emission variations 18
1.3.7 Bovine Serum Albumin-Driven emission variations 19
1.4. Conclusion 31
1.5. References 33
Chapter 2
Ionic complex of rhodamine dye with aggregation-induced emission property
2. 1 Introduction 40
2. 1. 1 Fluorescence of Rhodamine 40
2. 1. 2 Ionic complex with RdH(CSA)3 41
2.2. Experimental sections 42
2.2.1 Materials 42
2.2.2 Instrumentations 43
2.3 Results and discussion 44
2.3.1 Solution emission of RdH(CSA)x complexes 44
2.3.2 AIE property of RdH(CSA)3 46
2.3.3 NMR spectrum analysis 48
2.3.4 Metal ions-driven emission variations 51
2.3.5 RdH(CSA)3 as sensor for organic amines 52
2.3.6 Bovine Serum Albumin-Driven emission variations 54
2.4. Conclusion 61
2.5. References 62
Supporting Information 67

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