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研究生: 陳書婷
Shu-ting Chen
論文名稱: 具推拉電子基之二苯基苯、萘、蒽之合成及其光物理研究
Study on Synthesis and Photophysics of Diphenyl Benzene, Naphthalene, Anthracene with Electron Donor and Acceptor Groups
指導教授: 何郡軒
Jinn-Hsuan Ho
口試委員: 蔡伸隆
Shen-Long Tsai
蔡協致
none
學位類別: 碩士
Master
系所名稱: 工程學院 - 化學工程系
Department of Chemical Engineering
論文出版年: 2014
畢業學年度: 102
語文別: 中文
論文頁數: 140
中文關鍵詞: 推拉電子基二苯基萘二苯基蒽
外文關鍵詞: donor acceptor, diphenylnaphthalene, diphenylanthracene
相關次數: 點閱:196下載:2
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具π共軛(π conjugation)之分子及高分子已廣泛應用於有機光電材料,而材料的吸收及放射光波長之調控,可以由有機分子結構之設計來達成。除了利用增長線性π共軛分子之長度外,加入推拉電子基(ElectronDonor and Acceptor)於π共軛分子的兩側所形成之D-π-A分子,會具有分子內電荷轉移之能力,也是有效使吸收及螢光光譜紅移並調控其波長的方法。
當分子結構中同時含有推電子基(Donor)與拉電子基(Acceptor)的共軛系統,
透過光的激發和π軌域重疊的共軛性,電子可由推電子基轉移到拉電子基上,使
分子具有分子內電荷轉移(intramolecular charge transfer,ICT)的特性,此分子構
形經常被拿來探討。
聚聯苯化合物(polyphenylenes)為常見的π共軛系統,其具推拉電子基的衍生物顯示其具有分子內電荷轉移的效果3。而近年來,萘(naphthalene)及蒽(anthracene) 也逐漸成為光電材料研究的π共軛單元。相較於聚苯化合物,其結構特徵為「具有垂直於線型π共軛主鏈之額外苯環」。運用萘及蒽單元於π共軛系統中,可能提供更多共軛π軌域之好處,但也可能存在具較大兩面角之結構破壞軌域重疊之缺點。因此,我們合成了具推拉電子基之1,4-二苯基苯、1,4-二苯基萘、1,4-二苯基蒽及9,10-二苯基蒽四個系列化合物及其相對應之分子,有系統的研究萘及蒽在D-π-A分子系統中之影響。


π-conjugatedmolecular and polymeric materials have been used on the organic photoelectronics, and we can design the molecular structure of organic materials to regulate the molecular absorption and emission wavelength.In addition to increase the linear π conjugation length ,adding the electron donor and acceptor in π-conjugated D-π-A molecule will have the ability to cause charge transfer within the molecule and regulate its photophysics .The molecular structure which has a πconjugated system with electron donor and acceptor, through the light excitation and electron transfer via overlapped π orbitalsfrom electron donor to acceptor,has the characteristics of intramolecular charge transfer .
In recent years, naphthalene and anthracene are studied in application on the π conjugated units of optoelectronic materials. Compared with polyphenylenes, naphthalene and anthracene possess the structure of " with an additional benzene perpendicular to the π-conjugated main chain ",the use of naphthalene and anthracene units in π-conjugated systems may either provide more conjugated π orbitals or lead to a larger dihedral angle that may destroy the original π conjugation.
Thus, we study on synthesis and photophysics of diphenyl benzene, naphthalene, anthracene with electron donor and acceptor groups.

第一章 緒論 1 1.1 有機光電材料(Organic photovoltaic materials) 1 1.2光物理程序(Photophysical process)8,9 2 1.3分子電子躍遷形式 4 1.4在D-π-A系統電荷轉移 6 1.5溶劑效應(solvent effect) 7 1.6 Stokes shift31 9 1.7偶極矩探討 10 1.8螢光量子產率(fluorescence quantum yield) 13 1.9相關文獻回顧 15 1.10研究動機與探討 17 第二章結果與討論 19 2.1 化合物結構與代號 19 2.2 化合物的合成 22 2-3 化合物於溶液中之光物理研究 25 2-3 結構對化合物光物理性質的影響 53 2-3-1以萘為主體的推電子、拉電子、具推拉電子化合物比較 53 2-3-2以蒽為主體的推電子、拉電子、具推拉電子化合物比較 55 2-3-4 各化合物比較 60 2-4 Stokes shift 62 2-5 分子基態及激發態偶極矩 64 2-6螢光量子產率 76 第三章結論 77 第四章實驗部份 80 4-1 實驗儀器 80 4-2 實驗藥品與溶劑 81 4.3 吸收度量測方法 83 4.4 螢光量子產率之量測方法 85 4.5化合物結構、分子式與分子量 86 4.6化合物之合成步驟 88 References 102

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