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毕业论文-聚芘衍生物的合成及其荧光性质的研究，共76页，30988字
中文摘要
共轭聚合物一般指的是具有共轭?键长链结构的聚合物，这类材料具有优异的
光学性能。近年来，共轭聚合物因为其有机电子发光器件、化学及生物传感器等
方面的潜在应用已引起了广泛关注，其中芘和寡聚芘及其衍生物具有较高的荧光
量子产率，是良好的光学探针分子，已在荧光传感方面有所应用。但是由于寡聚
芘主链刚性且缺乏侧链，溶解性差，限制应用。烷氧基是一种可以调节聚合物性
质的取代基，它可以增加聚合物主链上的电子云密度，降低聚合物带隙及氧化电
位，增强聚合物的荧光量子产率，同时改善聚合物的溶解性。本文设计并合成两
种带烷氧基侧链的聚芘衍生物——寡聚（1-甲氧基芘）和寡聚（1-乙氧基亚磷酸
芘钠）并研究其在传感方面的应用。寡聚（1-甲氧基芘）由电化学聚合方法合成，
可以溶于一般有机溶剂中，并在许多溶剂中表现出了溶致荧光变色效应。其荧光
在聚集态时很弱，但是溶剂化后显著增强。据此性质开发了一种通过荧光开启检
测挥发性芳香化合物的传感薄膜。寡聚（1-乙氧基亚磷酸芘钠）综合化学和电化
学方法合成，为水溶性聚电解质。其在水溶液由于分子聚集而荧光极弱，但是加
入一定量的表面活性剂可以使其荧光恢复。三价铁离子的存在可以使寡聚（1-乙
氧基亚磷酸芘钠）荧光淬灭，利用这一性质实现了水溶液中三价铁离子的选择性
检测，检测限可达 10?8 M。
关键词：寡聚芘衍生物；共轭聚电解质；烷氧基侧链；传感

ABSTRACT
Over the past decades, conjugated polymers have been widely investigated
because of their unique structures and properties. Conjugated polymers are usually
have strong fluorescence and can be used as probing molecules for chemical and
biological sensors. Among these polymers, polypyrene or oligopyrene and its
derivatives have high fluorescent quantum yields and have been used as fluorescence
probes in chemical sensing systems. However, the solubility of oligopyrene is rather
low because of its rigid backbone and lacking of grafted chains. On the other hand,
alkoxy can enhance the electron densities of aromatic monomers. As a result, the
oxidation potentials of the monomers are lowered and the band gaps and solubility of
the polymers are improved. In this dissertation, two derivatives of oligopyrene with
alkoxy side groups, oligo( methoxy pyrene) and oligo(oxyethyl orthophosphorous
pyrene acid), are designed and synthesized successfully. Oligo( methoxy pyrene) is
synthesized by electrochemical polymerization and it is soluble in common organic
solvents and exhibits fluorescence solvatochromic effect. The fluorescence emission of
aggregated polymer is weak but the fluorescent can be enhanced dramatically when
polymer chains are solvated. Therefore, a turn-on fluorescent gas sensor was fabricated
based on this polymer. Oligo(oxyethyl orthophosphorous pyrene acid) is synthesized
by the combination of chemical and electrochemical synthesis methods and it is
soluble in water. The emission of its aqueous solution is very weak due to the
aggregation of polymer chains. However, adding surfactant can strongly increase its
fluorescence intensity. The presence of Fe3+ can quench the fluorescence of the
aqueous solution of the oligomer. Thus, oligo(oxyethyl orthophosphorous pyrene acid)
was used as fluorescence probe for the selective detection of Fe3+ in aqueous solution,
and the detection limit was measured to be 10?8 M.
Keywords：oligopyrene derivatives; conjugated polyelectrolyte; alkoxy; sensor

目录
第 1 章 引 言 ....1
1.1 共轭聚合物 1
1.1.1 共轭聚合物的特点及其应用 .1
1.1.2 共轭聚合物的一般合成策略 .2
1.1.3 共轭聚电解质 .......5
1.2 聚芘的合成及应用 ....6
1.2.1 未取代聚芘的合成及应用 .....6
1.2.2 聚芘衍生物的合成及应用 ...10
1.3 课题的提出和研究内容 ...19
第 2 章 寡聚（ 1-甲氧基芘）的合成及基于荧光性质的应用 ..21
2.1 实验方法 .21
2.1.1 原料 ....21
2.1.2 仪器 ....21
2.1.3 OMOPr 的合成 .....22
2.1.4 荧光测试 .....23
2.2 结果与讨论 ......23
2.2.1 OMOPr 的电化学性质 .23
2.2.2 OMOPr 的光谱性质 .....26
2.2.3 荧光传感性质 .....28
2.3 本章小结 .31
第 3 章 寡聚（ 1-乙氧亚磷酸芘钠）的合成及基于荧光性质的应用 .......32
3.1 实验方法 .32
3.1.1 原料 ....32
3.1.2 仪器 ....32
3.1.3 OPPr 的合成 33
3.2 结果与讨论 ......36
3.2.1 1-乙氧基亚磷酸二乙酯芘的电化学性质 ......36
3.2.2 聚合物 OPPrNa 的光谱性质 37
3.2.3 荧光传感性质 .....41
3.3 本章小结 .44
第 4 章 结论 ....45
插图索引 ...46
参考文献 ...50
致 谢 .54
声 明 .55
附录 A 外文资料书面翻译 .......56
在学期间参加课题的研究成果 ..67