共晶化合物的篩選、製備、鑑定、分子辨認及應用：

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研究生：	汪璞芸 Pu-Yun Wang
論文名稱：	共晶化合物的篩選、製備、鑑定、分子辨認及應用： Screening, Manufacturing, Characterization, Molecular Recognition and Applications of Co-crystals: Cytosine with Dicarboxylic Acids
指導教授：	李度 Tu Lee
口試委員:
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程與材料工程學系 Department of Chemical & Materials Engineering
畢業學年度：	98
語文別：	英文
論文頁數：	190
中文關鍵詞：	胞嘧啶、分子辨認、光致螢光、共晶化合物
外文關鍵詞：	co-crystal, cytosine, molecular recognition, photoluminescence
相關次數：	點閱：14 下載：0
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晶體材料從固體中分子的排列，及改變分子之間位置和/或相互作用，其通常對一特定固體的特性有直接影響，藉以獲得基本的物理特性。該晶體形式的多樣性驅動獨特的物化性質。固體形式的發現和設計取決於感興趣分子的性質和其在發展上面臨各種物性的挑戰。
結晶工程已發展出以自組裝現有分子的方式產生廣泛的新型固體形式，而不需破壞或形成共價鍵。此結構特徵可以被視為經由特定的相互作用進行一系列分子辨認的結果。以共晶化合物來量身訂作材料特性，已激發許多研究人員在結晶工程領域的興趣。
儘管有大量關於共晶化合物的文獻，但大部分仍主要集中在活性藥物成分的探討。本論文的目的是採用目前發展在活性藥物成分上的優勢，來創造奇特的超分子結構，並調控一方便的、有系統的、有效率的，及貼近量產條件的方法來篩選，製造和鑑定共晶化合物。胞嘧啶(cytosine)已被選定為這項研究中作為共晶化合物的主成分，和一系列增加脂肪鏈長度的二羧酸(dicarboxylic acids)，HOOC(CH2)nCOOH (n= 0 至 2)被選定為共晶化合物的共同組成者。選擇溶劑微量研磨法(solvent-drop grinding)為共晶化合物的篩選方法，而採用溶液結晶法(solution crystallization)製備共晶化合物。我們製造的共晶化合物中胞嘧啶間的分子辨認和超分子異模塊(supramolecular heterosynthons)可能被用於研究胞嘧啶特有的分子印記和DNA蛋白質結合的理論設置。實驗室常見的分析工具，如PXRD，DSC，TGA，IR，OM，EA和SXD被用來了解超分子結構，並確認共晶化合物的品質。結果共產生4:1胞嘧啶－草酸二水合物、2:1胞嘧啶－丙二酸，和2:1胞嘧啶－琥珀酸的共晶化合物。之前，大多數研究共晶化合物的物理和化學性質主要來自製藥業，因此沒有提到共晶化合物關於光學性質的文獻。因此，我們希望製作共晶化合物用於光學元件上，其中具有光電特性的共晶化合物之光致發光強度，可以透過改變各種共晶化合物的共同組成者來調整，如果經由控制與優化，將可廣泛用於有機發光二極管(OLED)，甚至生物發光二極管(BioLED)的製程上。

The crystalline materials obtain their fundamental physical properties from the molecular arrangement within the solids, and altering the placement and/or interactions between these molecules can usually have a direct impact on the properties of a particular solid. The crystal form diversity drive unique physicochemical properties. Solid form discovery and design depends on the nature of the molecule of interest and the type of physical property challenges faced in its development.
Crystal engineering has evolved in such a manner that it invokes self-assembly of existing molecules to generate a wide range of new solid forms without the need to break or form covalent bonds. The structural features can be regarded as the result of a series of molecular recognition events via specific interactions. Co-crystals have excited the interest of many researchers in the crystal engineering field as a way to tailor-make material properties.
Despite of a large number of literatures about co-crystals, most paper focused mainly on active pharmaceutical ingredients (APIs). The aim of this thesis is to take the full advantage of those current advancements in APIs to creat exotic supramolecular architectures and to concoct a convenient, systematic, efficient, and close-to-scale-up-conditions method for screening, manufacturing, and characterization of co-crystal. Cytosine has been chosen for this study mainly as a co-crystal component with a series of dicarboxylic acids of increasing aliphatic chain length, HOOC(CH2)nCOOH (n= 0 to 2) were selected as co-crystal co-formers. The solvent-drop grinding method was selected to be the co-crystal screening method and solution crystallization was used for co-crystal manufacturing. The molecular recognition among cytosines and the supramolecular heterosynthons of our fabricated co-crystals might be used for the investigation of theoretical sites of cytosine specific to molecular imprint and DNA-binding proteins. Common laboratory analytical tools such as PXRD, DSC, TGA, FT-IR, OM, EA, and SXD were used to understand the supramolecular architectures and to ensure the quality of co-crystals. 4:1 co-crystal of cytosine-oxalic acid dihydrate, 2:1 co-crystal of cytosine-malonic acid, and 2:1 co-crystal of cytosine-succinic acid were manufactured.
Formerly, most of those who study the physical and chemical properties of the co-crystal compound were from the pharmaceutical industry, and thus there was no literature mentioning the optical properties of co-crystals. Therefore, we hope to fabricate co-crystal compounds for optical devices in which the photoluminescence (PL) intensity of the co-crystal compounds having optoelectronic properties could be tuned by varying the kinds of co-crystal co-formers. It could widely be applied in the manufacturing process of organic light-emitting diodes (OLED), or even biologic light-emitting diodes (BioLED).

Table of Contents
摘要.............................................................................................................................................i
Abstract	……………………………………………………………………………………….iii
Acknowledgement	v
Table of Contents	vii
List of Tables	xi
List of Figures	xii
Chapter 1  Executive Summary	1
1.1	Introduction	1
1.2	Brief Introduction of Cytosine	5
1.3	Conceptual Framework	7
1.4	References	9
Chapter 2  Analytical Instruments	13
2.1	Introduction	13
2.2	Thermal Analysis	16
2.2.1	Differential Scanning Calorimetry (DSC)	16
2.2.2	Thermal Gravimetric Analysis (TGA)	19
2.3	Crystallography	22
2.3.1	Powder X-ray Diffractometry (PXRD)	22
2.3.2	Single-Crystal X-ray Diffractometry (SXD)	25
2.4	Spectroscopic Instrument	29
2.4.1	Fourier Transform Infrared (FT-IR) Spectroscopy	29
2.4.2	Solid-State Nuclear Magnetic Resonance (SSNMR)	31
2.4.3	Photoluminescence Spectroscopy (PL)	35
2.5	Microscopic Methods	38
2.5.1	Optical Microscopic (OM)	38
2.5.2	Hot Stage & Polarizing Optical Microscopy (HSOM)	40
2.6	Elemental Analysis (EA)	42
2.7	Conclusions	45
2.8	Reference	46
Chapter 3	  Solubility, Polymorphism, Crystallinity, and Crystal Habits of Cytosine by Initial Solvent Screening	51
3.1	Introduction	51
3.1.1	Solubility	53
3.1.2	Crystal Habits	54
3.1.3	Polymorphism	55
3.1.4	Crystallinity	58
3.2	Materials	59
3.2.1	Cytosine	59
3.2.2	Solvents	62
3.3	Experimental Methods	66
3.3.1	Initial solvent screening	66
3.3.2	Instrumental Analysis	69
3.4	Results and Discussion	72
3.4.1	Solubility	72
3.4.2	Crystal Habits	76
3.4.3	Polymorphism	79
3.4.4	Crystallinity	85
3.5	Conclusions	87
3.6	References	88
Chapter 4	  Screening, Manufacturing and Characterization Techniques of Co-Crystals: Cytosine with Dicarboxylic Acids	94
4.1	Introduction	94
4.1.1	Material candidate and design	95
4.1.2	The aim of co-crystal formation	96
4.1.3	Review of co-crystal screening/manufacturing	97
4.2	Materials	100
4.3	Experimental Section	102
4.3.1	Co-crystal screening procedures	102
4.3.2	Co-crystal formation procedures	103
4.3.3	Analytical Instruments	104
4.3.4	Solubility Study	110
4.4	Results and Discussion	112
4.4.1 Screening Results  112
4.4.2 Characterization  115
4.4.3 Solubility Study  147
4.4.4 Photoluminescence (PL)  151
4.5 Conclusions  153
4.6 References  154
Chapter 5 Conclusions and Future Works 162
5.1 Initial Solvent Screening  162
5.2 The Co-crystals of Cytosine with Dicarboxylic Acids 163
 
List of Tables
Table 2.1 Summary on the characterization capacities of the analytical apparatuses	15
Table 3.1 23 kinds of solvents in our experiments.	63
Table 3.2 Form space of cytosine, the solvents were arranged by Hildebrand values.	73
Table 3.3 Molar enthalpy and entropy of dissolution of cytosine in different solvents.	75
Table 3.4 Aspect ratios of the cytosine recrystallized by temperature cooling method in different good solvents.	77
Table 3.5 Aspect ratios of cytosine crystals re-crystallized from 4 kinds of anti-solvents.	78
Table 3.6 The enthalpy of melting and crystallinity of cytosine crystals by temperature cooling in 2 kinds of good solvents.	86
Table 3.7 The enthalpy of melting and crystallinity of cytosine monohydrate by an anti-solvent method.	86
Table 4.1 The information of the chemicals.	101
Table 4.2 IR assignments of cytosine, dicarboxylic acids, and co-crystals of cytosine with dicarboxylic acids.	124
Table 4.3 Elemental analysis of co-crystals of cytosine-oxalic acid dihydrate, cytosine-malonic acid, and cytosine-succinic acid.	132
Table 4.4 Crystallographic data of co-crystals and cytosine monohydrate.	138
Table 4.5 Selected bond lengths (Å) of the co-crystals and cytosine monohydrate.a	139
Table 4.6 Selected bond angles (o) of the co-crystals and cytosine monohydrate.a	140
List of Figures
Figure 1.1 Schematic map of the common solid forms and their respected compounds.1	2
Figure 1.2 The chemical structure of cytosine.	6
Figure 2.1 Schematic diagram of a DSC. The triangles are amplifiers that determine the difference in the two input signals.  The sample heater power is adjusted to keep the sample and the reference at the same temperature during the DSC scan.	18
Figure 2.2 (a) Heat flux DSC, (b) power-compensated DSC (S = Sample pan; R = Reference pan).	19
Figure 2.3 A Perkin Elmer DSC 7 differential scanning calorimeter.	19
Figure 2.4 A Perkin Elmer TGA 7 thermogravimetric analyzer.	21
Figure 2.5 Diffraction of Bragg’s Law.	23
Figure 2.6 A Bruker Axs D8 Advance PXRD.	25
Figure 2.7 Schematic representation of a four-circle diffractometer.	27
Figure 2.8 The steps involved in a crystal structure determination.	27
Figure 2.9 A Siemens SMART CCD-based X-ray diffractometer equipped with Oxford Cryosystems low temperature device.	28
Figure 2.10 A schematic illustration of FTIR operation system.	30
Figure 2.11 A Perkin Elmer Spectrum One FT-IR spectrometer (Perkin Elmer, New York, USA).	31
Figure 2.12 Schematic representation of the MAS technique.  The spinning axis of the sample is at an angle of 54.74o (magic angle) with respect to static magnetic field B0.	32
Figure 2.13 Solid-state NMR experiments were performed on a Varian Infinityplus-500 NMR spectrometer.	35
Figure 2.14 Schematic illustration of luminescence processes.	37
Figure 2.15 Perkin Elmer LS-55 Fluorescence spectrometer..	37
Figure 2.16 Light paths of the optical microscopy	39
Figure 2.17 Olympus SZII (Tokyo, Japan) optical microscopy.	39
Figure 2.18 Olympus BX-51 optical microscope and Linkam Scientific Instruments Ltd CI94 hot stage.	41
Figure 2.19 Schematic diagram of an automatic C, H, and N analyzer.	43
Figure 2.20 Heraeus vario EL-III-NCSH (Elementar Company, Germany) elemental analyzer.	43
Figure 2.21 The workflow for screening and manufacturing co-crystals which contained of all of the used analytical instruments.	45
Figure 3.1 Typical Solubility curve and a cooling crystallization path from A to D.	54
Figure 3.2 Solubility diagram for enantiotropic polymorphism.  Form I was the stable form below the transition temperature, while Form II was the metastable one.  Above the transition point (Ttr), Form I became metastable, while Form II became stable.	56
Figure 3.3 Solubility diagram for monotropic polymorphism.  Form I was considered the thermodynamically stable polymorph, while Form II was the kinetically stable (metastable) polymorph.	57
Figure 3.4 The molecule structure of anhydrous cytosine.	60
Figure 3.5 The structure (a) cytidine is the nucleoside of cytosine in RNA and (b) deoxycytidylate is the nucleotide of cytosine in DNA.	60
Figure 3.6 (a) The Watson-Crick base pair, cytosine forms three hydrogen bonds with guanine and (b) the Hoogsteen base pair, thymine forms two hydrogen bonds with adenine.	60
Figure 3.7 Cytosine has two tautomeric forms, the amino form and imino form.	61
Figure 3.8 (a) TGA data and (b) DSC thermogram at a heating rate of 10oC/min of the purchased cytosine for use test.	62
Figure 3.9 The recrystallization of cytosine by temperature cooling.	67
Figure 3.10 Solubility curve of cytosine in the good solvents.	74
Figure 3.11 The Van’t Hoff plots of the solubility values of cytosine in 2 different kinds of good solvents.	76
Figure 3.12 OM images of (a) cytosine monohydrate solids grown from water, and (b) cytosine solids grown from DMSO.	77
Figure 3.13 OM images of the cytosine monohydrate crystals recrystallized from 4 kinds of anti-solvents in an aqueous solution.  (a) THF at 60oC, (b) 1,4-dioxane at 60oC, (c) acetonitrile at 60oC, and (d) acetone at 50oC.	78
Figure 3.14 (a) TGA data and (b) DSC thermogram at a heating rate of 10oC/min the cytosine monohydrate re-crystallized from water by the cooling method.	80
Figure 3.15 The PXRD pattern of (a) cytosine monohydrate and (b) the purchased cytosine .	80
Figure 3.16 The FT-IR spectra of (a) the cytosine monohydrate and (b) the purchased cytosine .	81
Figure 3.17 (a) TGA scan and (b) DSC thermogram at a heating rate of 10 oC/min of cytosine re-crystallized from DMSO by temperature cooling.	82
Figure 3.18 The PXRD pattern of (a) cytosine re-crystallized from DMSO by temperature cooling and (b) purchased cytosine.	82
Figure 3.19 The FT-IR spectra of (a) cytosine re-crystallized from DMSO by temperature cooling and (b) the purchased cytosine.	83
Figure 3.20 DSC thermograms of cytosine monohydrate recrystallized for three different anti-solvents of (a) 1,4-dioxane at 60oC, (b) acetonitrile at 60oC, and (c) acetone at 50oC, which compared with (d) the purchased anhydrous cytosine.	84
Figure 3.21 The TGA thermograms of cytosine monohydrate recrystallized for three different anti-solvents of (a) 1,4-dioxane at 60oC ((100-13.56)g/ 111.1 g/mol : 13.56g/ 18g/mol = 0.778: 0.753 = 1:1), (b) acetonitrile at 60oC ((100-13.24)g/ 111.1 g/mol : 13.24g/ 18g/mol = 0.781: 0.736 = 1:1), and (c) acetone at 50oC ((100-13.66)g/ 111.1 g/mol : 13.66g/ 18g/mol = 0.777: 0.753 = 1:1).	84
Figure 3.22 The PXRD pattern of cytosine monohydrate recrystallized for the three different anti-solvents of (a) 1,4-dioxane at 60oC, (b) acetonitrile at 60oC, and (c) acetone at 50oC, which compared with (d) the purchased anhydrous cytosine, and (e) cytosine monohydrate. (where * represented the anhydrous cytosine peak.)	85
Figure 4.1 Molecular Structures of (a) cytosine, (b) oxalic acid, (c) malonic acid, and (d) succinic aicd.	100
Figure 4.2 DSC heating curves of (a), (b) and (c) are physical mixtures of cytosine and malonic acid at 1:1, 1:2, 2:1 molar ratios respectively. The purchased compounds of (d) cytosine, and (e) malonic acid.	112
Figure 4.3 PXRD data for the complex prepared by the solvent-drop grinding method of (a) cytosine-oxalic acid dihydrate (2:1), and the purchased compounds of (b) oxalic acid dihydrate, (c) cytosine. (* represented the new peak relative to the starting materials.)	114
Figure 4.4 PXRD data for the complex prepared by the solvent-drop grinding method of (a) cytosine-malonic acid (2:1), and the purchased compounds of (b) malonic acid, (c) cytosine.  (* represented the new peak relative to the starting materials.)	114
Figure 4.5 PXRD data for the complex prepared by the solvent-drop grinding method of (a) cytosine-succinic acid (2:1), and the purchased compounds of (b) succinic acid, (c) cytosine.  (* represented the new peak relative to the starting materials.)	115
Figure 4.6 The optical micrographs of (a) cytosine monohydrate, the co-crystals of (b) CmOAn, (c) CmMAn, and (d) CmSAn.	116
Figure 4.7 PXRD patterns of (a) solution crystallized co-crystal of CmOAn, (b) water-drop ground mixture of cytosine and oxalic acid dihydrate , (c) oxalic acid dehydrate, and (d) cytosine (* indicated the new appearing diffraction peak).	117
Figure 4.8 PXRD patterns of (a) solution crystallized co-crystal of CmMAn, (b) water-drop ground mixture of cytosine and malonic acid, (c) malonic acid, and (d) cytosine (* indicated the new appearing diffraction peak).	117
Figure 4.9 PXRD patterns of (a) solution crystallized co-crystal of CmSAn, (b) water-drop ground mixture of cytosine and succinic acid, (c) succinic acid, and (d) cytosine (* indicated the new appearing diffraction peak).	118
Figure 4.10 (a) TGA data and (b) DSC thermogram at a heating rate of 10oC/min for the co-crystal of CmOAn•xH2O prepared by the cooling method.	119
Figure 4.11 (a) TGA data and (b) DSC thermogram at a heating rate of 10oC/min for the co-crystal of CmMAn prepared by the cooling method.	119
Figure 4.12 (a) TGA data and (b) DSC thermogram at a heating rate of 10oC/min for the co-crystal of CmSAn prepared by the cooling method.	120
Figure 4.13 FTIR spectra of (a) cytosine, (b) oxalic acid dihydrate, and (c) the cocrystal of CmOAn•xH2O.	122
Figure 4.14 FTIR spectra of (a) cytosine, (b) malonic acid, and (c) the cocrystal of CmMAn.	122
Figure 4.15 FTIR spectra of (a) cytosine, (b) succinic acid, and (c) the cocrystal of CmSAn.	123
Figure 4.16 1H MAS NMR spectra of (a) cytosine, (b) oxalic acid dihydrate, (c) the cocrystal of CmOAn•xH2O.	127
Figure 4.17 1H MAS NMR spectra of (a) cytosine, (b) malonic acid, (c) the cocrystal of CmMAn.	127
Figure 4.18 1H MAS NMR spectra of (a) cytosine, (b) succinic acid, (c) the cocrystal of CmSAn. (* indicated the –COOH peak).	128
Figure 4.19 13C CP MAS NMR spectra of (a) cytosine, (b) oxalic acid dihydrate, (c) the cocrystal of CmOAn•xH2O.	128
Figure 4.20 13C CP MAS NMR spectra of (a) cytosine, (b) malonic acid, (c) the cocrystal of CmMAn.	129
Figure 4.21 13C CP MAS NMR spectra of (a) cytosine, (b) succinic acid, (c) the cocrystal of CmSAn. (* indicated the –COOH peak).	129
Figure 4.22 (a) PXRD pattern from solution crystallization by cooling, and (b) theoretical PXRD pattern from SXD of the co-crystal of C4OA1•2H2O.	136
Figure 4.23 (a) PXRD pattern from solution crystallization by cooling, and (b) theoretical PXRD pattern from SXD of the co-crystal of C2MA1.	136
Figure 4.24 (a) PXRD pattern from solution crystallization by cooling, and (b) theoretical PXRD pattern from SXD of the co-crystal of C2SA1.	137
Figure 4.25 Visualization of the (a) ORTEP plot of the molecular entities in the asymmetric unit of cytosine monohydrate, (b) hydrogen bonded layer formed by cytosine monohydrate, and (c) the packing diagram of the hydrogen-bonded layers of cytosine monohydrate as depicted by a computer software (Diamond 3.1, Crystal Impact Gbr, Brandenberg, Germany).  A dimeric unit of cytosine was labeled in a green dashed box.	142
Figure 4.26 Visualization of the (a) ORTEP plot of the molecular entities in the asymmetric unit of the cocrystal C4OA1•2H2O, (b) hydrogen bonded layer formed by cytosine and water molecules in the cocrystal C4OA1•2H2O, and (c) hydrogen-bonded layer formed by cytosine and oxalic molecules in the cocrystal C4OA1•2H2O (d) the packing diagram of the hydrogen-bonded layers of the cocrystal C4OA1•2H2O as depicted by a computer software (Diamond 3.1, Crystal Impact Gbr, Brandenberg, Germany). A dimeric unit of cytosine was labeled in a green dashed box.	144
Figure 4.27 Visualization of the (a) ORTEP plot of the molecular entities in the asymmetric unit of the cocrystal C2MA1, (b) hydrogen-bonded layer formed by cytosine and malonic molecules in the cocrystal C2MA1, and (c) the packing diagram of the hydrogen-bonded layers of the cocrystal C2MA1 as depicted by a computer software (Diamond 3.1, Crystal Impact Gbr, Brandenberg, Germany). A dimeric unit of cytosine was labeled in a blue dashed box.	145
Figure 4.28 Visualization of the (a) ORTEP plot of the molecular entities in the asymmetric unit of the cocrystal C2SA1, (b) hydrogen-bonded layer formed by cytosine and succinic molecules in the cocrystal C2SA1, and (c) the packing diagram of the hydrogen-bonded layers of the cocrystal C2SA1 as depicted by a computer software (Diamond 3.1, Crystal Impact Gbr, Brandenberg, Germany). A dimeric unit of cytosine was labeled in a blue dashed box.	146
Figure 4.29 The solubility curves of the cytosine (■), cytosine monohydrate (●), co-crystal C4OA1•2H2O (▲), co-crystal of C2MA1 (2:1) cocrystal (▼), and co-crystal of C2SA1 (◆).	147
Figure 4.30 PSD for cytosine-oxalic acid-water system at 25oC showing reactant solution concentrations ([cyt]T and [oxa]T) of the cocrystal (■) . Symbols indicated experimental data. Solid line represented the predicted dependence according to [cyt]T  = ( Ksp / [oxa]T )0.25 with Ksp = 8.21×10-12 m5. Measured solubility of cytosine and the cocrystal in pure RO water were indicated by ▲ and ●, respectively. The dashed line represented reactant stoichiometry in solution corresponding to that of co-crystals.	150
Figure 4.31 PSD for cytosine-malonic acid-water system at 25oC showing reactant solution concentrations ([cyt]T and [mal]T) of the cocrystal (■). Symbols indicated experimental data. Solid line represented the predicted dependence according to [cyt]T  = ( Ksp / [mal]T )0.5 with Ksp = 4.90×10-5 m3. Measured solubility of cytosine and the cocrystal in pure RO water were indicated by▲ and ●, respectively. The dashed line represented reactant stoichiometry in solution corresponding to that of cocrystals.	151
Figure 4.32 PSD for cytosine-succinic acid-water system at 25oC showing reactant solution concentrations ([cyt]T and [suc]T) of the cocrystal (■). Symbols indicated experimental data. Solid line represented the predicted dependence according to [cyt]T = ( Ksp / [suc]T )0.5 with Ksp = 3.11×10-6 m3. Measured solubility of cytosine and the cocrystal in pure RO water were indicated by ▲ and ●, respectively. The dashed line represented reactant stoichiometry in solution corresponding to that of cocrystals.	152
Figure 4.33 The PL emission spectra of commercially purchased (a) cytosine, (b)oxalic acid d1hydrate, (c) malonic acid, and (d) succinic acid.	153
Figure 4.34 The PL emission spectra of (a) the co-crystal C2MA1, (b) cytosine, (c) cytosine monohydrate, (d) the co-crystal C2SA1, and (e) the co-crystal C4OA1•2H2O.	153

                                

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