Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/3928
標題: 規則樹枝狀分子之製備及其應用研究
Synthesis and Application of Poly(urea/malonamide) Dendrons
作者: 張家振
Chang, Chia-Cheng
關鍵字: dendrimers
規則樹枝狀分子
self-assemibly behavior
honeycomb polymer films
polymer vesicles
macroporous MWNT films
自組裝行為
蜂窩狀高分子薄膜
高分子液胞
多孔性多壁奈米碳管薄膜
出版社: 化學工程學系所
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摘要: 本研究以4-isocyanato-4’(3,3-dimethyl-2,4-dioxo-azetidino) diphenylmethane (IDD)為構築單元,利用IDD一端為具反應性的isocyanate官能基和一端具反應選擇性的azetidine-2,4-dione官能基進行樹枝狀分子(dendrimers)之合成,製備出poly(urea/malonamide) dendrons。製備方式為加成反應,反覆利用IDD與diethyltriamine (DETA)進行反應,製備不同代數之dendrons。研究之dendrons外圍為C18長烷鏈段,相對較為疏水,且分子間具凡德瓦爾作用力;另外,dendrons內部為urea/malonamide結構,具有多氫鍵官能基。本研究主要利用此樹枝狀分子之特性,進行一系列自組裝之相關研究。 研究第一部分針對規則樹枝狀分子自組裝特性進行探討。實驗過程中一代的dendrons本身於THF溶液中有凝膠化(gelation)之現象;透過調配不同濃度之溶液,經XRD和SEM量測之結果顯示,dendrons之自組裝構型為層板(lamella),型態呈現如球莖。另外,實驗利用市售親水性之Jeffamine ED-2003為核心,與dendrons反應製備出具親疏水兩性之dumbbell shaped dendrimers,並於不同濃度下觀察其形態,由AFM、SEM和TEM結果顯示所形成之形態為微胞,隨導入代數增加其分子間作用力增加,穩定性也提升;進一步改變不同溶劑條件亦可以得到逆微胞之型態,進一步證明dendrimers在溶劑中之自組裝行為。 第二部分,實驗將dendrons導入高分子中,製備出側鏈規則樹枝狀高分子(dendritic side-chain polymers),由於dendrons本身具有多氫鍵官能基及分子間凡德瓦爾作用力,預期此特性有助於分子之自組裝;研究中利用Breath-figure程序和二次乳化法兩種方式驅使側鏈規則樹枝狀高分子進行自組裝,分別可自組裝得到蜂窩狀高分子薄膜及高分子液胞。實驗中探討dendrons在breath-figure方法製備蜂窩狀高分子膜中之影響和所扮演的角色,結果發現dendrons與高分子間的共價鍵結、適當的濃度和相對溼度是製備出良好蜂窩狀高分子薄膜的必要條件,合適的親疏水平衡也是重要的因素之一。另外,製備高分子液胞方面,實驗中探討不同pH值及乙醇的導入對製程的影響;研究中首先針對dendrons進行二次乳化程序,dendrons由於上述之特性,可以經此程序自組裝形成液胞;進一步地,側鏈規則樹枝狀高分子亦可經此程序自組裝形成液胞或多層乳化(multi-emulsion)球體,由於高分子主鏈的導入及dendrons自組裝的特性,有助於液胞的自組裝形成及增加液胞之穩定度。最後,研究利用dendrons改質多壁奈米碳管(MWNT),dendrons本身的特性可幫助奈米碳管於溶劑中的分散性;另一方面,由於dendrons經由程序可自組裝排列之特性,研究中直接利用改質碳管進行breath-figure程序,期望可以直接經由自組裝程序形成多孔性之薄膜,做進一步之利用。
In this study, the dual-functional building block 4-isocyanato-4''(3, 3-dimethyl-2, 4-dioxo-azetidino) diphenylmethane (IDD) was used to prepare dendrons via a convergent route. Utilizing high reactivity of isocyanate and selective reactivity of azetidine-2, 4-dione of IDD, the poly(urea/malonamide) dendrons were synthesized via sequential addition reactions of IDD and diethyltriamine (DETA). The dendrons accompanied with peripheral long alkyl chains and urea/malonamide linkages enhance the Van de Waals force at peripheral part and the hydrogen bonding interaction at the focal part, respectively. Herein, based on this advantageous and unique characteristic, a series of self-assembly researches was attempted. First, we focused on the self-assemibly behavior of dendrons. Generation one dendron with peripheral stearyl groups ([G1]-C18) was capable of forming a gel in THF. The morphology of various concentrations of dendrons was characterized by XRD and SEM. In addition, the Jeffamine ED-2003 was utilized as the core to prepare amphiphilic dumbbell shaped dendrimers. The morphology of various concentrations of dumbbell shaped dendrimers was investigated by AFM, SEM and TEM. The results showed that better micelle stability was achieved by the incorporation of the higher generations of dendrons. This is because of the presence of stronger intermolecular or intramolecular interactions. Moreover, ordered micelle morphologies were obtained in the water and organic solvents, respectively. Apart from that, the dendrons were grafted onto polymers to prepare the dendritic side-chain polymers. The dendrons with strong intermolecular hydrogen bonding interactions and Van de Waals forces are expected to facilitate self-assembly of the dendritic side-chain polymers. Consequently, by means of breath-figure and double emulsion process, honeycomb polymer films and polymer vesicles can be easily obtained, respectively. Herein, various factors, including the concentration, the generation of the dendritic side-chain polymers, relative humidity (RH), and the grafting ratio, were taken into account to prepare ordered honeycomb-like polymeric films. In addition, a suitable hydrophobic/hydrophilic segment ratio in the polymer is also an important factor. On the other hand, for the preparation of polymer vesicles, the self-assembly behavor of the dendritic side-chain polymers was investigated by using different pH values and content of ethanol during the double emulsion process. Indeed, vesicles could be obtained from dendrons using double emulsion process. Moreover, vesicles or multi-vesicles could also be obtained from the dendritic side chain polymers via double emulsion process. The presence of the dendrons in the polymer would enhance its self-assembly behavior and the stability of vesicles. Finally, a facile and versatile assembly process for highly entangled carbon nanotube scaffolds was presented. Multi-walled carbon nanotubes (MWNTs) modified with dendrons demonstrated improved dispersion. In addition, macroporous MWNT films were directly prepared by a breath figure process. The macroporous MWNT films are potentially useful for further applications such as optoelectronic devices, electrochemical devices, or energy storage.
URI: http://hdl.handle.net/11455/3928
其他識別: U0005-2908201110360600
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-2908201110360600
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