Synthesis of High Performance N-Heteroaromatic Organic Field Effect Transistors from Azides

本研究由化学系化学合成项目资助，由Tom G.伊利诺伊大学芝加哥分校化学系的司机将探索使用铑（II）催化的C-H键胺化反应从乙烯基叠氮化物中高效合成N-杂芳族材料的模块化设计和执行。 目标二吡咯并噻吩和N-杂环庚并苯是两类低分子量的N-杂环化合物，在薄膜有机场效应晶体管中表现出有希望的性能。 通过对N-取代基和芳香基团的合理改变，将确定其分子结构与N-芳香杂环材料的体相物理性质之间的关系，从而调控薄膜有机场效应晶体管的性能，这一研究目标的实现可能会改变用于构建N-芳香杂环材料的合成策略。 从容易获得的起始材料，C-H键官能化有效地建立了N-杂环核并产生N-H键，其使得能够容易地改变材料的溶解度。 通过研究所提出的N-杂芳族材料的性能，基本洞察这些材料的分子结构和本体物理性能之间的关系将获得。 通过这些研究获得的知识预计将使具有可预测的整体性质的材料的合理设计，以推进高性能可印刷有机电子产品。 此外，该项目将成为培养学生在科学事业中取得进步的沃土。 通过强调女性和代表性不足的少数民族学生的参与，该计划将有助于实现总统科技顾问理事会概述的目标，以改变和收取STEM学生管道。

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Tom G. Driver of the Department of Chemistry at the University of Illinois at Chicago will explore the design and execution of modular, efficient syntheses of N-heteroaromatic materials from vinyl azides using their rhodium(II)-catalyzed C-H bond amination reaction. The targeted dipyrrolothiophenes and N-heterocyclic heptacenes are two classes of low molecular weight N-heterocycles that exhibit promising properties in thin film organic field effect transistors. By making rational changes to both the N-substituent and aromatic groups, the relationship between the molecular structure and bulk physical properties of their N-heteroaromatic materials will be determined to allow the properties of thin film organic field effect transistors to be tuned.Achievement of the research goals might change the synthetic strategies used for the construction of N-heteroaromatic materials. From readily available starting materials, C-H bond functionalization efficiently establishes the N-heterocyclic core and produces an N-H bond that enables easy modification of the solubility of the material. By examining the properties of the proposed N-heteroaromatic materials, fundamental insight into the relationship between the molecular structure and bulk physical properties of these materials will be gained. The knowledge gained by these studies is anticipated to enable the rational design of materials with predictable bulk properties to advance high performance printable organic electronics. In addition, this project will serve as a fertile ground for the training of students to advance in their scientific careers. By emphasizing the participation of female and underrepresented minority students, this program will help meet the goals outlined by President's Council of Advisors on Science and Technology to transform and charge the STEM-student pipeline.