含phenazine單元的多環稠合共軛結構之合成途徑探索與其光學性質鑑定

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姓名

陳子銘(Zi-Ming Chen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

含phenazine單元的多環稠合共軛結構之合成途徑探索與其光學性質鑑定
(Exploration Toward The Synthesis and Optical Property Studies of The Conjugated Structures Based on Polyarene-fused Phenazines)

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摘要(中)

在本論文中，我們致力於開發有效的多環稠合共平面之-二酮的合成方法，並作為合成含吡嗪共軛結構的關鍵單元。至目前為止，我們已成功合成出兩種多環稠合共平面之-二酮的異構物(化合物9與化合物33)，並利用這類已開發成功的-二酮作為前驅物合成了數個小型模型染料分子。
我們對這些新開發的染料分子進行線性和非線性光學測量，並發現了以下特點：
[1] 當在模型分子中引入雜環單元(如:吡啶、塞酚)會使得分子之吸收峰與螢光放射峰產生紅移,但量子產率也會隨之降低。
[2] 增加推電子基的數量對於吸收與螢光的強度及雙光子吸收截面皆有正面幫助,但對於吸收峰與螢光放射峰的位置並沒有正相關。
[3] 提升分子共平面性有助於增加分子之吸收峰與螢光放射峰紅移程度。
[4] 在兩種-二酮的異構物當中,使用彎曲型的-二酮(化合物33)所構成的染料結構有更紅移的吸收峰與螢光放射峰

摘要(英)

In this thesis, we attempted to develop efficient synthetic procedure toward polycyclic and coplanar -diketones as the key synthons for various pyrazine-containing conjugation structures.
So far, we have successfully constructed the desired -diketones and have synthesized several small model compounds based on these developed -diketone isomers.
We have performed linear and non-linear optical property measurements on these newly synthesized chromophors and have found out the following features:
[1] When a heterocyclic unit( i.e. pyridine and thiophene) is introduced into this model system, the absorption peak of the molecule and the fluorescence emission peak are red-shifted, but the quantum yields are decreased.
[2] Increasing the number of electron-donating groups can enhance the intensity of absorption and fluorescence as well as two-photon absorptivities.
[3] Increasing the coplanarity of the molecule helps to increase the extent of red-shift about absorption peak and fluorescence emission peak.
[4] For the isomeric structures, the one constructed by using bent-shaped -diketone as the precursor manifests relatively red-shiftted absorption and emission bands.

關鍵字(中)

★ 多環
★ 共軛結構

關鍵字(英)

★ phenazine
★ Polyarene-fused Conjugated Structures

論文目次

中文摘要 I
Abstract II
目錄 III
表目錄 X
第一章雙光子吸收之特性與願景 1
1-1 雙光子吸收原理與歷史回顧 1
1-1-1 雙光子吸收原理 1
1-1-2 雙光子吸收歷史回顧 2
1-2 雙光子分子設計核心概念 3
1-3雙光子材料應用 5
1-4 研究動機與論文組成 6
參考文獻 7
第二章模型分子之設計理念與合成途徑 8
2-1 合成路徑開發歷史回顧 8
2-2 合成路徑之重大突破 16
2-3 模型分子之設計與合成 18
參考文獻 32
第三章光學性質之測量與探討 34
3-1 線性光學 35
3-2 非線性光學 44
第四章實驗用儀器及藥品 47
4-1 光學量測用儀器 47
4-2 實驗用藥品與溶劑 52
4-3 本論文模型分子之合成細節 54
第五章 NMR結構鑑定 92

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指導教授

林子超(Tzu-Chau Lin)

審核日期

2019-8-21

推文