(I) 脂肪性分解酵素於消旋形式2-芳香基環己醇之動力光學分割反應(II) 新型之藍色有機電激發光材料開發與研究

(I) Kinetic Resolution of Racemic 2-Arylcyclohexanols by Lipase (II) Synthesis and Characterization of Novel Blue Organic Light-Emitting Diode Materials

佘怡璇(Yi-Hsuan She)

指導教授 ： 劉行讓

國立清華大學/理學院/化學系/博士(2006年)

摘要

本論文係包含兩部分：第一部分報導利用脂肪性分解酵素(lipase AK)針對消旋形式2-芳香基環己醇，如：(±)-2-(1-萘基)-1-環己醇((±)-2-(1-naphthyl)cyclohexan-1-ol，1)與(±)-苯基環己醇((±)-2-phenylcyclohexanol，2)，進行動力光學分割反應(kinetic resolution)，以製備具高光學純度之鏡像異構物(+)-1與(-)-1，和(+)-2與(-)-2。經由多次實驗條件下，我們除了發現新的脂肪性分解酵素lipase AK可應用於化合物(±)-1與(±)-2的分離，得到具高純度之鏡像異構物，更意外發現其特殊的效果可以大量應用在工業量產上。第二部分報導有機發光二極體(OLED)之藍色電激發光材料的合成研究，並進一步探討其光電、物理、化學與元件特性等性質。這部分的主要工作方向有二，其一為利用有機合成方式合成新型Alq3衍生物。係於Alq3之8-羥基喹嚀(8-hydroxyquinoline)配位基上，嘗試引入不同的拉電子基及推電子基，形成新穎之化合物，再與鋁金屬作用，合成出具橘光、綠光與藍光新型化合物，如化合物7、化合物11、化合物16、化合物21、化合物22、化合物28、化合物35、化合物40、化合物41與化合物48等。另一為設計及製備具多苯取代茚類化合物之藍色電激發光材料，如化合物49與化合物83。這些研究內容之說明，將詳述於本論文。

關鍵字

Alq3衍生物 ； 多苯取代之茚類化合物

並列摘要

In this thesis, the research projects are inclusive of the kinetic resolution of racemic 2-aryl cyclohexanols by Lipase AK and the synthesis and photophysical studies of novel blue electroluminescent materials.
The first chapter of this thesis describes the investigation into the use of Lipase AK (Pseudomonas fluorescens) in the kinetic resolution of 2-arylcyclohexanols, resulting in a robust and effective process towards both (R,S)- and (S,R)-enantiomers of racemic 2-(1-naphthyl)- ((±)-1) and 2-phenylcyclohexanol ((±)-2) in high enantiomeric purity and excellent chemical yields. The low cost of raw materials, independency of reaction time, and the recyclability of the enzyme makes this newly developed process amenable for the large scale production of pure enantiomers of 1 and 2, both of which have found extensive utility as chiral auxiliaries in asymmetric synthesis.
The second chapter details the work towards the development of novel chemical entities suitable for incorporation into the organic light emitting diodes (OLEDs) with blue light emitting properties. The suitability and practicability of the newly generated materials in OLED applications were also investigated by determination of their electroluminescence as well as various photo- and chemophysical parameters. Towards this end, a plethora of substituted Alq3, a well documented electron transporting material, derivatives containing electron withdrawing and/or donating groups have been synthesized and characterized (i.e. 7, 11, 16, 21, 22, 28, 35, 40, 41, and 48).
Additionally, novel polyaryl-substituted indenes (i.e. 49 and 83) have been synthesized and found to possess properties suitable for blue light emitting OLEDs. Details of this project as well as the abovementioned investigation constitute this thesis.

並列關鍵字

Alq3 derivatives ； polyaryl-substituted indene derivatives

參考文獻

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