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    题名: Ⅰ.具N-苯環取代基之反式- 3 -二苯乙烯胺之合成與螢光性質之研究Ⅱ.具醯胺基與Pentiptycene之α,ω烷類雙硫醇化合物之合成
    作者: 涂志瑋;Zh-Wei Tu
    贡献者: 化學研究所
    关键词: 有機光化學;二苯乙烯
    日期: 2001-07-17
    上传时间: 2009-09-22 10:09:00 (UTC+8)
    出版者: 國立中央大學圖書館
    摘要: 本論文包含兩個部份第一部份為反式-3-二苯乙烯胺衍生物之合成與光化學性質研究,其中亦包括3-胺基和4-N,N-二苯胺基取代之1,2-二芳基乙烯化合物。合成藉由Horner-Emmons 反應、鈀-催化偶合反應、硝基還原反應與N-甲基化反應得到N-苯環取代之反式-3-二苯乙烯胺衍生物。吸收光譜顯示N-苯基會造成反式-3-二苯乙烯胺的主要吸收峰往藍位移方向移動且吸收增強,而螢光光譜則為紅位移且螢光量子產率則隨N-苯環取代數之增加而變小,然而當N-苯環之2,6位置為甲基時,螢光減弱不明顯。這些結果顯示胺基與二苯乙烯間的共軛性與螢光行為有密切關係,且與反式-4-二苯乙烯胺衍生物完全相反。 第二部份為合成一新的含Pentiptycene之雙硫醇分子以供其自我組成於有機金屬表面上之研究。此計畫為本實驗室過去研究之延伸,目的是要藉由具氫鍵形成潛力之醯胺基的加入來改善先前所合成之含Pentiptycene 的烷類雙硫醇化合物於金鉑表面上自我排列之規則度。目標物之合成乃由六個步驟完成,反應種類包括SN2反應、去保護反應、DCC偶合反應。進一步之量測目前仍進行中。 This thesis consists of two independent sections. The first section is the studies on the synthesis and photochemical behavior of trans-3-aminostilbene and its N-phenyl substituted derivatives. Several 3-amino and 4-N,N-diphenylamino substituted 1,2-diarylethylenes are also included. Target compounds were prepared based on the Horner-Emmons olefin synthesis, Pd-catalyzed C-N coupling reaction, and N-methylation reaction. Absorption spectra show blue shifts with increased intensity for 3-aminostilbenes upon N-phenyl substitutions; however, it is red-shifted in fluorescence spectra. Fluorescence quantum yields decrease for N-phenyl substituted 3-aminostilbenes, but the decrease in fluorescence quantum yields is only little for the case of N-phenyl group that contains dimethyl substituents at the 2 and 6 positions. These observations indicate that the fluorescence behavior of N-phenyl substituted 3-aminostilbenes is strongly related to the extent of conjugation between the amine and stilbene groups and is opposite to that of N-phenyl substituted 4-aminostilbenes. The second section is the synthesis of a new pentiptycene-derived dithiol for the investigation of its self-assembly behavior on the metal surface. This project follows the previous work in this laboratory and aims to improve the ordering of self-assembled monolayer by introducing the potential hydrogen-bonding amide groups to the alkyl chains. The synthetic procedures involve six steps, including SN2 reaction, deprotecting reaction, and DCC coupling reaction.
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