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

在这个由化学系化学合成计划资助的项目中，伊利诺伊大学芝加哥分校化学系的Tom G.Driver教授将探索设计和执行模块化、高效地从乙烯基叠氮化物合成N-杂芳烃材料的方法，该反应使用Rh(II)催化的C-H键胺化反应。靶向的二吡咯噻吩类和N-杂环庚烯类化合物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N-杂环化合物。通过对N-取代基和芳香族基团进行合理的改变，可以确定其N-杂芳族材料的分子结构与体物理性质之间的关系，从而使薄膜有机场效应晶体管的性能得以调整。这些研究目标的实现可能会改变用于构建N-杂芳族材料的合成策略。从容易获得的起始材料，C-H键功能化有效地建立了N-杂环核心，并产生N-H键，使材料的溶解度能够容易地改变。通过研究所提出的N-杂芳烃材料的性质，将从根本上深入了解这些材料的分子结构和整体物理性能之间的关系。通过这些研究获得的知识有望使具有可预测的整体性能的材料的合理设计能够促进高性能可打印有机电子设备的发展。此外，该项目将成为培养学生在科学职业生涯中取得进步的沃土。通过强调女性和代表不足的少数族裔学生的参与，该计划将有助于实现总统科学和技术顾问委员会提出的改造和管理STEM-学生渠道的目标。

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.