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    Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/3688


    Title: 對苯二乙烯衍生物的合成與光電性研究/ 合成含立體選擇性的α次甲基丁內酯化合物;Study of the Synthesis of Oligo(phenylenevinylene)s and Their Photophysical and Optoelectronic Properties / Stereoselective Synthesis of (Z)-a-Phenoxymethy- lene-g-butyrolactone from 2-Propynyloxybenzene
    Authors: 柯勝利;Sheng-Li Ko
    Contributors: 化學工程與材料工程研究所
    Keywords: 對苯二乙烯衍生物;丁內酯化合物;distyrylbenzene derivatives;butyrolactone
    Date: 2003-07-07
    Issue Date: 2009-09-21 12:20:11 (UTC+8)
    Publisher: 國立中央大學圖書館
    Abstract: 本研究主題之一是合成一系列在分子內不同位置上帶有拉電子的氰基 或推電子的甲氧基之二苯乙烯苯,或稱苯乙烯寡分子,並研究其吸收與放射光譜 及在電致發光上的性質。研究顯示,上述這些分子,可作填充劑置於電子傳輸層 內並放出藍光和綠光。正己氧基與2-乙正己氧基及氰基在苯乙烯寡分子的吸收與 放射光譜中的最大吸收與放射波長並無明顯的不同,但2-乙正己氧基在電致發光 二極體中可比正己氧基產生更純的藍光。推電子的甲氧基則會產生較偏綠光的電 致發光波長。研究結果也顯示具有高螢光量子產率的化合物未必具有高電致發光 之量子產率,反而具有較低螢光量子產率的化合物可具有較高的電致發光之量子 產率。帶有氰基及烷氧基之二苯乙烯苯,在鐵氟龍之表面上作摩擦-轉移後可作 取向附生性的生長。而此二苯乙烯苯與鐵氟龍之雙層材料也在吸收與放射光譜上 顯示出非比尋常的非等方性的特性。我們根據其吸收與放射光譜在平行與垂直方 向上呈45 度角的激發光之下得到的結果,提出三種分子在鐵氟龍表面上的可能 之立體排列狀態。亦即,與鐵氟龍之表面上摩擦方向有垂直,平行,和垂直與平 行三種空間的排列。原子力顯微鏡的結果與三種分子在鐵氟龍表面上的可能之立 體排列狀態也非常吻合。共軛型的炔酮類化合物在碘化鈉,氯化三甲基矽及水, 並以乙 作溶劑下,可進行反應得到產率及立體選擇性均佳的非共軛型的(順式)- 碘化烯酮類化合物。研究結果顯示3-癸炔-2-酮的反應是由先產生的碘化氫進行 炔基加成反應,得到(順式)-及(反式)-4-碘-3-癸烯-2-酮,再進行氯化三甲基矽催 化的非共軛化反應產生(順式)-4-碘-4-癸烯-2-酮。利用上述非共軛化反應,我們 成功地開發一種利用碘化非共軛烯酮的分子來合成在α-位置上帶有順式的苯氧 或苯硫取代基之碳-碳環外雙鍵丁內酯化合物。此類化合物可用來作為DNA 的 切割試劑,濃度可低至10 µM。 A series of distyrylbenzene (DSB) derivatives, as oligo(para-phenylene- vinylene) (OPV), were synthesized and assessed as the emitter in organic light emitting diode (OLED) fabrication. The presence of electron-withdrawing cyano group and electron-donating methoxy group at various positions in the molecule to evaluate their influence on the photophysical property and the electroluminescent behavior of these derivatives in OLED were studied. Bright blue emissions were achieved with these materials as a dopant. There were not much difference in the absorption and emission spectra of the compounds containing n-hexyloxy and 2-ethylhexyloxy groups. However, 2-ethylhexyloxy groups produce more saturated blue color in their EL. The compounds with higher fluorescent quantum yield did not result in higher EL quantum efficiency in this multiplayer OLED fabrication as that of compounds with lower fluorescent quantum yield. DSB derivatives with cyano and alkoxy groups grew epitaxially on the friction-transferred poly(tetrafluoroethylene) (PTFE) layer. DSBs/PTFE double layers indicated the remarkable anisotropic feature in absorption and emission properties. We concluded that trans,trans-1,4- di(2-ethyl-hexyloxy)-2,5-bis[2-(4-cyanophenyl)ethenyl]benzene molecules take two kinds of orientations on the PTFE layer in which the long axes of trans,trans-1,4-di(2-ethyl-hexyloxy)-2,5-bis[2-(4-cyanophenyl)ethenyl]benzene are parallel and normal to the substrate surface. On the other hand, the long axes of trans,trans-1,4-di(2-ethylhexyloxy)-2,5-bis[2-(2-cyanophenyl)ethenyl]- benzene and trans,trans-1,4-di(2-ethyl-hexyloxy)-2,5-bis[2-(3-cyanophenyl)-ethenyl]benzene ori- ent inclined and parallel to the substrate, respectively. Treatment of conjugated alkynone with NaI, TMSCl, and water in acetonitrile gave deconjugated (Z)-3-iodo-3-alken-1-one in good yield and with high stereoselectivity (≥95%). Mechanistic study showed that HI, generated from NaI, TMSCl and water, underwent regioselective addition to the conjugated y e.g. 3-decyn-2-one, to form (E)-4-iodo-3-decen-2-one and (Z)-4-iodo-3-decen-2- one. Then, TMSCl catalyzed the deconjugation reaction to form deconjugated (Z)-4-iodo-4-decen-2-one. The application of the above deconjugation reaction was demonstrated by the stereoselective synthesis of (Z)-α-phenoxy-methylene- γ-butyrolactone and its hydrofuran analogues. DNA cleavage study also showed that γ-butyrolactone with (Z)-configuration at α-alkylidene gave better result than its analogue even at 10µM for only 10 min. The development of an efficient method for the preparation of (Z)-α-phenoxy-methylene-γ-butyrolactone and (Z)-α-phenylthiomethyl-γ-butyro- lactone derivatives from 2-propynyoxybenzene and 2-propynylthiobenzene were described.
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