本研究以具有米氏酸官能基之多面體矽氧烷寡聚物(POSS)之合成與應用為主軸。第一階段利用Corner capping縮合反應合成帶有單一氯苯官能基之前驅物POSS-Ph-Cl 並利用FT-IR、1H-NMR、FD-MS、DSC證實其結構及性質。
第二階段將製備所得POSS-Ph-Cl作為反應物分別與米氏酸(MA)、具苯基米氏酸衍生物(MA-P)進行親核取代反應合成出帶有兩POSS取代基單體MA-D-POSS與單側POSS取代基單體MAP-POSS，後續利用FT-IR、1H-NMR、13C-NMR、FD-MS、DSC、TGA證實結構及性質分析。
第三階段為兩單體之後續應用，以米氏酸熱裂解產生之烯酮官能基作為基礎分為兩研究方向，第一部份利用烯酮官能基之自身二聚體反應及與4,4'-dihydroxybiphenyl的親核加成反應分別合成出帶有特定結構之巨型分子D-MA-D-POSS、D-MAP-POSS、L-MAP-POSS，後續利用FT-IR、13C-NMR、FD-MS、DSC、TGA進行各項鑑定，其中D-MA-D-POSS與D-MAP-POSS因無法溶解於各種有機溶劑中而無法確切證實其結構，但透過對於L-MAP-POSS之結構鑑定與性質分析仍可成功證實米氏酸衍生之高反應性烯酮官能基可用於奈米巨型分子之合成。第二部分將MAP-POSS作為添加劑，利用溶液成膜法製備PBz-oda/MAP-POSS複合薄膜並藉由烯酮官能基與PBz-oda開環交聯反應產生之酚基形成反應鍵結以導入POSS於PBz-oda材料之中，然而利用SEM所得到的細微結構觀察結果，可發現儘管利用米氏酸結構對POSS進行官能基改質，於PBz-oda高分子材料中仍可發現分布不均的現象，不過在熱穩定性方面則發揮了減緩裂解速率的作用，而POSS堅硬的籠狀結構也達到了顯著提升機械強度的效果。

This study focuses on the synthesis and application of Meldrum’s acid substituted POSS. In the first stage, mono phenyl chloride substituted POSS monomer, POSS-Ph-Cl is synthesized by corner capping condensation. By means of FT-IR, 1H-NMR, FD-MS and DSC, its structure and property are confirmed.
In the second stage, pre-prepared POSS-Ph-Cl reacts with Meldrum’s acid(MA) and phenyl substituted Meldrum’s acid(MA-P) separately to synthesize bi-POSS substituted Meldrum’s acid(MA-D-POSS) and mono-POSS substituted Meldrum’s acid(MAP-POSS). By means of FT-IR, 1H-NMR, 13C-NMR, FD-MS, DSC and TGA, their structures and properties are confirmed.
In the third stage, the study focus on the application of MA-D-POSS and MAP-POSS on the basis of the heat induced Meldrum’s acid derivative, ketene. This stage has two parts. In the first part, ketene derivatives of MA-D-POSS and MAP-POSS undergo [2+2]dimerization or react with nucleophilic hydroxyl agent of 4,4’-dihydroxyphenyl to obtain D-MA-D-POSS, D-MAP-POSS and L-MAP-POSS. Although the structures of D-MA-D-POSS and D-MAP-POSS aren’t attested exactly due to their poor solubility, successful analysis of L-MAP-POSS still confirm the feasibility of synthesis of nano giant molecule with highly reactive ketene. In the second part, PBz-oda/MAP-POSS composite membranes with different POSS content are prepared via solution method. During the crosslinking process, POSS is introduced into PBz-oda polymer with linkage formed from the reaction between ketene and PBz-oda ring-opening phenol byproduct. With the existence of POSS particle, the composite membranes show elevated performance in enhancing mechanical strength and retarding heat induced decomposition. However, the SEM results of prepared composite membrane show that the partial aggregatioin of MA-POSS still occur.

中文摘要 I
Abstract II
致謝 III
目錄 IV
圖目錄 VI
表目錄 X
第一章 緒論 1
1-1 前言 1
1-2 多面體矽氧烷寡聚物(POSS)之簡介 2
1-3米氏酸之簡介 11
1-4 研究目的 18
第二章 文獻回顧 19
2-1官能基改質POSS於複合材料之應用 19
2-1-1 物理性共混材料之性質與應用 19
2-1-2 具反應鍵結複合材料之性質與應用 25
2-2 具POSS結構巨型分子之構裝現象 31
2-3 米氏酸衍生物於改質之應用 35
第三章 實驗方法 39
3-1　實驗藥品 39
3-2 儀器設備 41
3-3 實驗流程圖 42
3-4 前驅物合成 43
3-4-1 MA-P合成60 43
3-4-2 POSS-Ph-Cl合成73 44
3-5 米氏酸改質POSS合成 45
3-5-1 MAP-POSS合成 45
3-5-2 MA-D-POSS合成 45
3-6 巨型分子製備 46
3-6-1透過烯酮二聚合反應製備 46
3-6-2透過烯酮之親合加成反應製備 46
3-7 PBz-oda高分子複合薄膜製備 47
第四章 結果與討論 48
4-1 前驅物鑑定 48
4-1-1 MA-P之鑑定 48
4-1-2 POSS-Ph-Cl之鑑定 51
4-2 米氏酸改質POSS鑑定 55
4-2-1 MAP-POSS鑑定 55
4-2-2 MA-D-POSS鑑定 61
4-3 Giant Molecule之鑑定 68
4-3-1 D-MAP-POSS之鑑定與分析 68
4-3-2 D-MA-D-POSS之鑑定與分析 71
4-3-3 L-MAP-POSS之鑑定與分析 75
4-4 PBz-oda/MAP-POSS薄膜之鑑定及性質分析 81
第五章 結論 86
第六章 參考文獻 87

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