RUI: Synthesis of Heterohelicenes Using Acetylene-Activated SNAr Reactions

科尔比学院化学系的Jeffrey Katz教授为化学合成项目提供支持。他正在研究一种化学方法，可以合成一种叫做螺旋烯的化合物。螺旋烯是一种不寻常的分子，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，使人们能够接触到分子末端位置上含有氮、氧、硫和硒原子的螺旋烯。这类化合物在化学传感器、有机电子学和新型高分子材料方面具有潜在的应用前景。参与该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少数族裔学生进入化学和其他科学领域。他担任Colby Achievement Program in the Sciences （CAPS）的联合主任，这是Colby College为来自弱势背景的一年级学生开设的夏季桥梁项目，旨在培养少数族裔学生科学群体的成功和领导氛围。螺旋烯及其异芳变体是一种很有前途的化合物，可作为手性配体、超分子构件、聚合单体、液晶、光电材料和分子机器的组成部分。利用乙炔活化SNAr/阴离子环化化学作为关键的多样化转化，可获得多种[n]杂螺旋烯，这是Katz实验室最近开发的反应级联。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旋烯，以及适应该方法来生产端杂芳烃。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。卡茨教授通过组织和主持本科生背景会议来利用他参加这些会议的机会，这些会议为所有参加会议的本科生提供了教育环境。这些课程被包括在几个有机化学主要会议的一般课程中，并帮助本科生成为越来越被认可的课程结构的焦点。

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.