Synthetic Advances for Conjugated Material Synthesis

点击翻译按钮获取中文摘要

Our research is focused on tackling synthetic challenges posed in the context of conjugated organic materials. These materials are poised to make significant technological breakthroughs that will enable the advancement of flexible, lightweight, low-cost electronic devices such as photovoltaics, light emitting diodes and field-effect transistors. Innovative new synthetic capabilities will allow the design of novel molecular architectures. Ultimately, this will lead to enhanced properties for these new materials and, therefore, improved device performances. This proposal outlines three projects in pursuit of these goals. Thiophenes represent one of the most important classes of compounds found in both conjugated polymer and small molecule organic materials. Herein, a new catalytic thiophene synthesis and polymerization for thiophene-based materials is proposed. The method should improve upon and provide complimentary reactivity to, existing methods allowing for the expedient assembly of novel thiophene-based polymeric materials. The biaryl motif is heavily in a variety of chemical fields and is a prevalent feature of conjugated organic materials. While traditional cross-coupling reactions prove useful synthetic tools, direct C-H bond arylation has recently emerged as a more efficient alternative. However, many drawbacks remain to be solved for direct arylation to become of truly broad synthetic utility. Herein, we propose designing catalyst/ligand structures specifically meant to solve some of these challenges by using a recent emerging mechanistic framework as a guide to catalyst design. Poly(p-phenylene vinylene)s (PPV) are a class of conjugated polymers which were among the first to be utilized for cutting-edge organic electronic applications and yet remain relatively unexploited. This is due in large part to limited synthetic accessibility of PPV-type polymers which not only hampers the design and testing of new derivatives but also restricts available properties of synthetically attainable polymers. Herein, we propose an alternative approach to PPV-type conjugated polymers by utilizing the C-H bond as a synthetic handle and exploiting transition-metal-catalyzed hydroarylation reactivity. The new polymerization reaction should prove valuable given the simple monomers required, its atom economical nature and ability to synthesize otherwise inaccessible polymeric structures. We also outline the opportunity that the proposed synthetic advances will provide an opportunity for the efficient construction of large libraries of functional conjugated organic materials. Long-term goals of this research program include utilizing the synthetic techniques to obtain previously inaccessible conjugated materials to be screened in a variety of exciting organic electronic applications.