RUI: Synthesis of Heterohelicenes Using Acetylene-Activated SNAr Reactions

化学系化学合成计划支持科尔比学院化学系教员杰弗里·卡茨教授的这一项目。他正在研究一种化学方法，这种方法可以合成被称为螺烯的化合物。螺烯是一种特殊的分子，具有刚性的螺旋(螺旋状)形状。这项资助研究的主要目标是开发一种技术，使人们能够在分子的末端位置获得以前未知的含有氮、氧、硫和硒原子的螺旋烯。这类化合物在化学传感器、有机电子学和新型聚合物材料等方面具有潜在的应用前景。从事这个项目的学生正在获得有机化学合成和材料化学方面的经验。卡茨教授非常积极地招募和留住未被充分代表的少数民族学生进入化学和其他科学领域。他是科尔比科学成就计划(CAPS)的联席主任，这是科尔比学院的夏季桥梁计划，旨在让来自代表性不足的背景的一年级学生进入该计划，在少数学生科学群体中培养成功和领导力的氛围。螺烯及其杂芳烃变体是一种很有前途的化合物类别，可用作手性配体、超分子构建块、聚合单体、液晶、光电材料和分子机器的部件。利用乙炔激活的SnAR/阴离子环化化学作为关键的多样化转化，可以获得多种[n]杂螺烯，这是Katz实验室最近开发的一种反应级联反应。级联方法是高效的、高度模块化的，并允许在合成序列的最后阶段实现结构多样化。此外，研究的目标是通过在级联序列的SNAR步骤中使用手性亲核试剂来生产非外消旋杂螺烯，以及改进该方法以产生端芳烃杂环芳烃。与卡茨教授一起工作的本科生前往科学会议，展示他们的研究成果。Katz教授通过组织和主持本科生背景会议来利用他的出席这些会议，这支持了所有参加本科生的教育环境。这样的会议被包括在有机化学的几个主要会议的一般计划中，并帮助本科生成为越来越多人认识到的计划结构的重点。

The Chemical Synthesis Program of the Chemistry Division supports this project by Professor Jeffrey Katz, a faculty member in the Department of Chemistry at Colby College. He is investigating chemical methods that allow for the synthesis of chemical compounds called helicenes. Helicenes are unusual molecules that possess a rigid helical (screw-like) shape. The primary goal of the funded research is the development of technology that allows access to previously unknown helicenes containing nitrogen, oxygen, sulfur, and selenium atoms on terminal positions of the molecules. Compounds of this type have potential applications as chemical sensors, organic electronics, and new polymeric materials. Students working on this project are obtaining experience in organic chemical synthesis and materials chemistry. Professor Katz is highly active in the recruitment and retention of underrepresented minority students into chemistry and other scientific fields. He serves as co-Director of the Colby Achievement Program in the Sciences (CAPS), a summer bridge program at Colby College for entering first-year students from underrepresented backgrounds that fosters a climate of success and leadership within the minority student science population.Helicenes and their heteroaromatic variants are a promising compound class for use as chiral ligands, supramolecular building blocks, polymerization monomers, liquid crystals, optoelectronic materials, and components of molecular machines. A wide variety of [n]heterohelicenes are being accessed using acetylene-activated SNAr/anionic cyclization chemistry as the key diversifying transformation, a reaction cascade recently developed in the Katz laboratory. The cascade approach is efficient, highly modular, and allows for structural diversification at the final stages of the synthetic sequence. Further, the investigations target the production of non-racemic heterohelicenes through the use of chiral nucleophiles in the SNAr step of the cascade sequence, as well as adaptation of the method to produce heteroarene-terminated phenacenes. Undergraduate students working with Professor Katz travel to scientific conferences to present their research. Professor Katz leverages his attendance at these meetings by organizing and moderating Undergraduate Context Sessions, which support the educational environment for all attending undergraduate students. Such Sessions are included in the general programs of several major conferences in organic chemistry and have helped undergraduate students to become an increasingly recognized focus of the program structures.