在本實驗中，製備了帶有芘官能基的氧代氮代苯并環己烷(Py-Bz)，是一種由芘-1-胺(Py-NH2)、苯酚(Phenol)與多聚甲醛(Paraformaldehyde)在甲苯/乙醇的共溶劑環境下所合成出的小分子。Py-NH2的製備是利用硝酸作為硝化劑合成具有芳香親電性取代的芘，對1-硝基芘(Py-NO2)進行催化還原。其中，利用液態核磁共振氫譜(1H NMR)，液態核磁共振碳譜(13C NMR)、傅立葉紅外線光譜儀(FTIR)與元素分析儀(EA)來鑑定新單體之化學結構，再利用示差掃描量熱儀(DSC)、傅立葉紅外線光譜儀(FTIR)來研究聚氧代氮代苯并環己烷-芘(Py-Bz)的固化反應，之後將Py-Bz與單壁碳管(Single-walled carbonnanotubes, SWCNTs)進行混摻，形成有機-無機(Py-Bz/ SWCNTs)複合材料，發現帶有官能基芘的聚氧代氮代苯并環己烷可以增強單壁碳管在THF溶劑中的分散性。接著利用螢光光譜儀(PL)發現Py-Bz與SWCNTs間存在π-π鍵作用力，再利用示差掃描量熱儀(DSC)、熱重分析儀(TGA)、動態機械性質分析(DMA)瞭解Py-Bz固化後的熱穩定性、熱重損失以及動態機械性質等。

In this study we prepared a new class of pyrene-functionalized benzoxazine (Py-Bz) through the reaction of phenol, paraformaldehyde, and 1-aminopyrene (Py-NH2) in toluene/ethanol co-solvents. 1-Aminopyrene was prepared through the catalytic reduction of the 1-nitropyrene (Py-NO2), which was synthesized by electrophilic aromatic substitution of pyrene by using nitric acid as nitration agent. We used 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared (FTIR) spectroscopy and Elemental analysis (EA) to confirm the chemical structure of this new monomer and then employed differential scanning calorimetry (DSC) and FTIR spectroscopy to study the curing behavior of the new Py-Bz polybenzoxazine. The presence of the pyrene-functionalized benzoxazine can enhance the mixing with single-walled carbon nanotubes (SWCNTs) in THF solution led to the formation of highly dispersible Py-Bz/ SWCNT organic/inorganic hybrid complex materials. Fluorescence emission spectra revealed significant π–π stacking between the Py-Bz and the SWCNTs in these complexes. In addition, incorporating SWCNT into the Py-Bz matrix significantly enhanced the thermal stability of this polybenzoxazine after thermal curing, as evidenced using differential scanning calorimetry, thermogravimetric, and dynamic mechanical analysis.

目錄
摘要 I
ABSTRACTII
目錄 III
圖目錄V
表目錄VIII
圖示目錄IX
第一章 緒論1
1.1 前言1
1.2 研究動機3
第二章 文獻回顧 4
2.1 氧代氮代苯并環己烷之聚合反應4
2.2 聚氧代氮代苯并環己烷之奈米複合材料5
第三章 實驗方法與步驟9
3.2 合成方法11
3.2.1 製備3-(pyren-1-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazin(Py-Bz)11
a. 合成1-Nitropyrene (Py-NO2)11
b. 合成1-aminopyrene (Py-NH2)11
c.合成(pyren-1-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazin (Py-Bz)11
3.2.2 Py-Bz/ SWCNTs之混摻與交聯12
第四章 初步結果與討論15
4.1 1-NITROPYRENE (PY-NO2) 與 1-AMINOPYRENE (PY-NH2) 鑑定分析15
4.1.1 Py-NO2與Py-NH2合成鑑定分析15
4.2PYRENE-BENZOXAZINE (PY-BZ)合成鑑定與性質分析20
4.2.1 Py-Bz合成鑑定分析20
4.2.2 Py-Bz交聯後性質分析 25
4.3 PYRENE- BENZOXAZINE (PY-BZ)與SINGLE-WALLED CARBON NANOTUBES (SWCNTS) 混摻性質分析28
4.3.1 Py-Bz/ SWCNTs分散性質探討28
4.3.2 Py-Bz/ SWCNTs交聯分析31
第五章 結論39
第六章 參考文獻 41

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