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

在这个由化学部门化学合成项目资助的项目中，伊利诺伊大学芝加哥分校化学系的Tom G. Driver教授将探索利用铑（II）催化的C-H键胺化反应，从乙烯基叠氮化物中设计和实现模块化、高效的n -杂芳香材料合成。靶向二吡咯噻吩和n杂环七烯是两类在薄膜有机场效应晶体管中表现出良好性能的低分子量n杂环化合物。通过合理改变n -取代基和芳香族基团，可以确定n -杂芳香族材料的分子结构和体物理性能之间的关系，从而调整薄膜有机场效应晶体管的性能。研究目标的实现可能会改变n -杂芳烃材料的合成策略。从现成的起始材料，C-H键功能化有效地建立了n -杂环核心，并产生了一个N-H键，使材料的溶解度易于修改。通过研究所提出的n -杂芳材料的性质，将获得对这些材料的分子结构和体积物理性质之间关系的基本见解。通过这些研究获得的知识有望使具有可预测体积特性的材料的合理设计能够推进高性能可印刷有机电子产品。此外，该项目将为培养学生在科学事业上的进步提供肥沃的土壤。通过强调女性和未被充分代表的少数族裔学生的参与，该项目将有助于实现总统科学技术顾问委员会（Council of Advisors on Science and Technology）提出的目标，即改变和充实stem学生储备。

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.