羊毛甾醇被報導具有減少水晶體上的蛋白結晶，可以眼藥水方式有效的治療白內障，並透過實驗也發現了羊毛甾醇的濃度對於白內障的治療具有相關性。由於大部分羊毛甾醇衍生物的水溶性不佳，故無法提高治療區域濃度而侷限期臨床應用。本篇論文將具有不同水溶性的官能團結合到羊毛甾醇骨架上，期盼改善這些新衍生羊毛甾醇化合物的水溶性，並利用這些化合物對白內障進行生物試驗。
另外，近期聚集誘導發光(aggregation induced emission, AIE)特性引起許多人的興趣。目前已經發現許多分子結構顯示出AIE現象。目前已被報導具有AIE性質常見的分子架構並不多，主要為四苯乙烯和六苯基噻咯兩類，因此尋找具AIE現象的新分子架構將成為未來進展基礎和應用拓展關鍵。在本論文中，結合上述兩者的結構特性開發了三苯基(三苯基乙炔基)苯，期待展現AIE現象。

Lanosterol derivatives were reported to show effective reduction of aggregation of lens crystalline proteins for treating cataract which is known to be caused by clumping of crystalline proteins to cloud eyes. The reduction of aggregation of crystalline proteins was found to be lanosterol-concentration-dependent. However, the lanosterol compounds examined were with low water solubilities which hampered practical applications. In this report, functional groups with different water solubilities are incorporated onto the lanosterol skeleton. The water solubilities of these newly derivatized lanosterol compounds are examined and the biological investigation of these compounds on cataract is studied. 
Aggregation-induced emission (AIE) or aggregation-modulated emission (AME) properties have attracted much attention. There have been several molecular skeletons found to show AIE phenomenon. The two well-known molecular frameworks showing AIE are tetraphenylethene and
hexaphenylsilole. Developing new molecular skeletons showing AIE is a must to advance fundamentals and applications. In this thesis, combining the structural features of the two mentioned above, triphenyl(triphenylethynyl)benzenes has been investigated to show AME phenomenon.

目錄	
目錄		I
圖表目錄	Ⅲ
附圖目錄	Ⅵ
第一章 簡介	1
1.1 白內障與羊毛甾醇簡介與研究動機	1
1.2 聚集誘導放射材料簡介	4
1.2.1 AIE與構像平面化	7
1.22 AIE與RIV	9
1.2.3 AIE與TICT	11
1.2.4 AIE與J-聚集體形成	13
1.2.5 AIE發光材料與應用	15
1.3 聚集誘導放射材料研究動機	16



第二章 實驗與合成	19
2.1 實驗簡介	19
2.2 儀器設備	20
2.3 實驗藥品	23
2.4 合成步驟	25
第三章 結果與討論	32
3.1合成討論	32
3.2羊毛甾醇衍生物之生物試驗	36
3.3 三苯(三炔苯)苯材料之聚集調配放射螢光光譜	38
3.4 晶體結構模擬與解析	44
3.5 結論	50
參考資料	51
附錄		56















圖表目錄
圖1、lanosterol結構	1
圖2、(2-Hydroxypropyl)-β-cyclodextrin結構	2
圖3、利用羊毛甾醇治療前(左)與治療後(右)之照片22	3
圖4、噻咯化合物(silole compound 1-methyl1,2,3,4,5-pentaphenylsilole)的螢光光譜圖。7(A) 水與乙醇90:10體積比溶液下、無水乙醇以及固體薄膜，濃度為10 mM (B) 化合物在不同THF/ H2O體積比下的量子產率。(C) 噻咯化合物 (1-methyl1,2,3,4,5-pentaphenylsilole)分子結構	5
圖5、化合物在不同體積比之acetonitrile/H2O溶液下之吸收與放射光譜 (10 µM) of (A) 1, (B) 2, and (C) 3; 激發波長為350 nm. (D) 化合物在UV燈下之acetonitrile溶液與粉末之圖片。37	7
圖6、TPE、THBDBA與BDBA之結構。(A) THBDBA在不同THF/ H2O體積比下的螢光強度(B) THBDBA與BDBA在不同THF/ H2O體積比下之螢光差異圖。38	9
表7、TPE、THBDBA與BDBA之吸收與放射光譜性質比對圖表	10
圖8、化合物BODIPY 13 (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene derivative)的螢光光譜圖29 (A) 化合物在不同THF/ H2O體積比下之螢光光譜圖比較 (B) 化合物在不同THF/ H2O體積比下的量子產率。	12
圖9、晶體結構與晶體在365nm的UV燈波長下(a)具有J-aggregates的9,10-MADSA 和(b) 具有H-aggregates的9,10-PADSA	13
圖10、365nm的UV燈波長下的固體照片以及兩化合物之螢光光譜(激發波長為355 nm)之 (a)具有J-aggregates的9,10-MADSA 和(b) 具有J-aggregates的9,10-PADSA	14
圖11、文獻已發表常見的AIEgens分子	15
圖12、tetraphenylethene (TPE) 與 hexaphenylsilole (HPS)之結構	16
圖13、(A)為六苯(苯)結構(B)為六炔苯(苯)結構(C)為1,3,5三炔苯三苯(苯)結構(D)為1,2,4三炔苯(三苯)苯結構	17
圖14、吸收光譜在 optical density (OD) = 450 nm 波長下, LS1與羊毛甾醇之澄清水晶體能力之比較。	37
圖15、化合物5a在(A)不同比例之THF/H2O環境下以302 nm紫外燈照射圖片 (B)化合物5a不同比例THF/ H2O環境下之螢光光譜圖，激發波長為309 nm		39
圖16、化合物5a在不同比例下的THF/ H2O在396 nm波長之螢光相對強度，激發波長為309 nm	40
圖17、化合物5b在(A)不同比例之THF/H2O環境下以302 nm紫外燈照射圖片 (B)化合物5b不同比例THF/ H2O環境下之螢光光譜圖，激發波長為312 nm		41
圖18、化合物5b在不同比例下的THF/ H2O (A) 394 nm與(B) 444 nm波長下之螢光相對強度激發波長為312 nm	42
圖19、LE態轉變至TICT態示意圖	42
表20、分子5a與5b在不同比例下的THF/ H2O之最大螢光波長 (λem)、波長位移 (λshift) 、量子產率 (ΦF)。	43
圖21、化合物5a之單晶分子結構俯視圖與側視圖	44
圖22、化合物5a之苯環與苯環最短間距	45
圖23、化合物5a之spartan軟體模擬的能量最佳化結構之電子雲分布圖			46
圖24、化合物5a的單晶結構氫原子與氟原子的分子間氫鍵關係	46
圖25、化合物5b之單晶分子結構俯視圖與側視圖	47
圖26、化合物5b之spartan軟體模擬的能量最佳化結構之電子雲分布圖			48
圖27、化合物5b之stacking 作用力	48
圖28、化合物5b的單晶結構氫原子與氟原子的分子間氫鍵	49


















附圖目錄
附圖1、化合物LS1之1H NMR光譜 (CDCl3, 600 MHz)。	57
附圖2、化合物LS1之13C NMR光譜 (CDCl3, 150 MHz)。	58
附圖3、化合物LS2之1H NMR光譜 (CDCl3, 600 MHz)。	59
附圖4、化合物LS2之13C NMR光譜 (CDCl3, 150 MHz)。	60
附圖5、化合物5a之1H NMR光譜 (CDCl3, 600 MHz)。	61
附圖6、化合物5a之13C NMR光譜 (CDCl3, 150 MHz)。	62
附圖7、化合物5b之1H NMR光譜 (CD2Cl2, 300 MHz)。	63
附圖8、化合物5b之13C NMR光譜 (CD2Cl2, 150 MHz)。	64
附圖9、化合物之LS2質譜分析。	65
附圖10、化合物之5a質譜分析。	66
附圖11、化合物之5b質譜分析。	67
附圖12、化合物5b之元素分析測量。	68
附圖13、化合物4之單晶繞射分析結果。	69
附表14、化合物4之單晶繞射數據及結構分析。	70
附圖15、化合物5a之單晶繞射分析結果。	73
附表16、化合物5a之單晶繞射數據及結構分析。	74
附圖17、化合物5b之單晶繞射分析結果。	83
附圖18、化合物5b之單晶繞射數據及結構分析。	84
附圖19、化合物5a粒徑在不同比例THF/H2O溶劑下測量。	88
附圖20、化合物5b粒徑在不同比例THF/H2O溶劑下測量。	90
附圖21、化合物5a於偏光顯微鏡下，在液相以速率為10 oC/min回溫至固相圖。(38 oC，scale bar: 100 μm，物鏡倍率: 10X)	92
附圖22、化合物5b於偏光顯微鏡下，在液相以速率為10 oC/min回溫至固相圖。(155 oC，scale bar: 100 μm，物鏡倍率: 10X)	92
附圖23、化合物5a之UV/PL疊圖，PL激發波長為309 nm，濃度為1x10-5 M in THF	93
附圖24、化合物5b之UV/PL疊圖，PL激發波長為309 nm，濃度為1x10-5 M in THF	93

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