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A versatile cross-coupling/cyclization methodology for the synthesis of fused polycyclic aromatics: Application to molecular and polymeric systems.

机译：一种用于合成稠合多环芳族化合物的通用交叉偶联/环化方法：在分子和聚合物系统中的应用。

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摘要

The research reported herein describes synthetic and physical investigations into molecular and polymeric conjugated organic systems; more specifically fused polycyclic aromatic systems. Central to this work was the use of Pd catalyzed cross-coupling chemistry which allowed for the ready construction of a variety of conjugated frameworks. Also critical to this work was the development of an electrophile-induced cyclization reaction which utilizes electron-rich triple bonds. The cyclization, which often proceeds in very high to quantitative yields, constitutes one of only very few direct routes into fused polycyclic systems. Chapter 2 describes the development of this cyclization reaction and describes the all-carbon and heterocyclic systems which have been prepared using the reaction. In addition, the results of studies aimed at elucidating the mechanism will be discussed. The preparation of all-carbon fused polycyclic aromatic polymers or graphite ribbons, the ultimate goal of this research, is described in Chapter 3. Also described are the results of studies performed on substituted pentaphenylene systems which serve as more extended models of the polymer systems. The goal of these studies was to determine the degree to which the polymer or graphite ribbon systems contained structural irregularities.; The use of photoluminesence spectroscopy proved invaluable in these studies and serves as a sensitive probe of structural defects. This sensitivity is derived from the extended conjugated nature of these systems which allows for energy migration over long distances and hence permits efficient sampling of the electronic systems of these materials. The conscious exploitation of this property by carefully choosing defect sites allows for the preparation of materials which may be used as sensory materials. Chapter 4 describes such a system which uses host-guest interactions to provide the structural irregularity. The synthesis and unusual photophysical properties of a calixarene functionalized poly(phenylenebithiophene) which selectively binds Na{dollar}sp+{dollar} over K{dollar}sp+{dollar} and Li{dollar}sp+{dollar} ions is described. The observation of a digital or on/off photoluminescent response is also described.
机译：本文报道的研究描述了对分子和聚合物共轭有机体系的合成和物理研究。更具体地讲，稠合多环芳族体系。这项工作的核心是使用Pd催化的交叉偶联化学技术，可以方便地构建各种共轭骨架。对于这项工作也至关重要的是开发利用富电子三键的亲电试剂诱导的环化反应。环化反应通常以很高的产率进行定量，是进入稠合多环系统的极少数直接途径之一。第2章介绍了该环化反应的进展，并介绍了使用该反应制备的全碳和杂环系统。另外，将讨论旨在阐明该机制的研究结果。全碳稠合多环芳族聚合物或石墨带的制备是本研究的最终目标，在第3章中进行了描述。还描述了对取代的五亚苯基系统的研究结果，该系统用作聚合物系统的更扩展模型。这些研究的目的是确定聚合物或石墨带系统中含有不规则结构的程度。在这些研究中，光致发光光谱学的使用被证明是无价的，并且可以作为结构缺陷的敏感探针。这种敏感性源自这些系统的扩展共轭性质，该共轭性质允许长距离能量迁移，因此可以对这些材料的电子系统进行有效采样。通过仔细选择缺陷部位来有意识地利用此特性，可以制备可用作感觉材料的材料。第4章介绍了这样一种系统，该系统使用主机－来宾交互来提供结构上的不规则性。描述了杯芳烃官能化的聚苯撑联噻吩的合成和非寻常的光物理性质，该聚苯撑噻吩可选择性地在Na +和Na +离子上与Na +离子和Li + +离子结合。还描述了对数字或开/关光致发光响应的观察。

著录项

  • 作者

    Goldfinger, Marc B.;

  • 作者单位

    University of Pennsylvania.;

  • 授予单位 University of Pennsylvania.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 1996
  • 页码 306 p.
  • 总页数 306
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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