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Investigations of opto-electronically interesting materials featuring phosphorus-carbon double bonds.

机译:具有磷-碳双键的光电子学材料的研究。

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摘要

Molecules and polymers featuring pi-conjugation have garnered much attention due to their applications in opto-electronic materials. The electronic properties of organic polymers can be "tuned" by altering the band gap between the HOMO and LUMO through doping, changing the length of conjugation, grafting functional groups and side chains onto the building blocks of the polymers, or incorporating elements that are active participants in the conjugation. The introduction (n-type) or removal (p-type) of electrons into the pi-conjugated system of the polymer is critical for the formation of new materials having practical applications as molecular switches, photovoltaics, sensors, and organic light emitting diodes.;Due to the similarities between phosphorus and carbon (based on electronegativity), phosphorus is often referred to as a "carbon copy" and the introduction of phosphorus into carbon-based systems is seen in many examples throughout the literature. Phosphaalkenes are analogous to alkenes and feature a double bond between the phosphorus and carbon atoms. Phosphaalkenes, of the form 4-R-2,6-Mes2C6H2P=C(H)C6H 4-4-R' (where R = H or MeO and R' = H or CN), with potential use in nonlinear optical materials, were studied using cyclic voltammetry to determine the effects of electron-withdrawing and electron-donating substituents on the reduction potential.;Incorporation of phosphorus into the main chain of an oligomeric or polymeric material has met some challenges because of the lack of stability in air, due to the reactive P=C bond, and the lack of planarity, due to steric hindrance, which causes a loss in the pi-conjugation between the P=C pi-system and aromatic pi-system of the phenyl ring. The next step in designing compounds which overcome these issues was by incorporating the P=C unit into a ring structure, thus preventing rotation and loss of conjugation. Heterophospholes, specifically 1,3-benzoxaphospholes and benzobisoxaphospholes, present such an option for study. In this report, detailed efforts to synthesize, characterize, and determine the redox behavior of these two systems has been investigated.
机译:具有π共轭特性的分子和聚合物由于在光电材料中的应用而备受关注。可以通过掺杂改变HOMO和LUMO之间的带隙,改变共轭长度,将官能团和侧链接枝到聚合物的结构单元上,或掺入活性元素,从而“调节”有机聚合物的电子性能。参加变身。将电子引入(n型)或除去(p型)电子到聚合物的π-共轭体系中对于形成具有实际应用的新材料至关重要,例如分子开关,光伏,传感器和有机发光二极管。 ;由于磷和碳之间的相似性(基于电负性),磷通常被称为“碳拷贝”,并且在整个文献中的许多示例中都将磷引入基于碳的系统中。磷烯烃类似于烯烃,并且在磷和碳原子之间具有双键。形式为4-R-2,6-Mes2C6H2P = C(H)C6H 4-4-R'的磷烯烃(其中R = H或MeO,R'= H或CN),可用于非线性光学材料,用循环伏安法研究了吸电子和给电子取代基对还原电势的影响。由于在空气中缺乏稳定性,将磷掺入低聚物或高分子材料的主链中遇到了一些挑战,由于反应性P = C键,并且由于位阻而导致平面度不足,这导致苯环的P = C pi系统和芳族pi系统之间的pi共轭损失。设计克服这些问题的化合物的下一步是将P = C单元并入环结构,从而防止旋转和结合损失。杂磷,特别是1,3-苯并恶唑和苯并二恶唑,为研究提供了这样的选择。在本报告中,已经研究了综合,表征和确定这两个系统的氧化还原行为的详细工作。

著录项

  • 作者单位

    Case Western Reserve University.;

  • 授予单位 Case Western Reserve University.;
  • 学科 Chemistry, Polymer.
  • 学位 Ph.D.
  • 年度 2010
  • 页码 217 p.
  • 总页数 217
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 ;
  • 原文服务方 国家工程技术数字图书馆
  • 关键词

    ;

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