Achiral and Chiral Nanographene Synthesis Using an Alkyne Linchpin Strategy

在化学系化学合成项目的支持下，内华达大学的Wesley Chalifoux正在研究用小而精确的分子构建块制造纳米石墨烯的方法。纳米石墨烯是一种扁平的碳原子薄片，它模仿了石墨烯的一小部分。纳米石墨烯的光电特性使其在有机发光二极管（oled）、有机场效应晶体管（ofet）和有机太阳能电池等应用中具有吸引力。Chalifoux研究小组正在努力开发制造这些分子的新方法，为下一代设备的设计提供支持。Chalifoux博士和他的学生团队正在温和的条件下将可修改的化学构建块转化为纳米石墨烯，并监测构建块的特定变化如何调整纳米石墨烯的特征，包括它们的三维形状和光学特性。这些活动还支持高中生参与化学研究，以鼓励他们参与科学，并支持他们向成功的科学、技术、工程和数学（STEM）职业发展。Wesley Chalifoux和他的研究小组正在推进炔苄环制程的使用，作为一种温和而通用的策略来制备具有可调光学特性的纳米石墨烯。高能含炔前体的使用允许使用温和的苯并化条件，支持扩展的官能团耐受性，并提供使用其他方法无法实现的各种纳米石墨烯结构。Chalifoux团队将把这一策略应用于高度扭曲和手性纳米石墨烯分子支架的合成，这种支架具有圆偏振光特性，可以用于各种chiroptic应用，如液晶显示、手性传感、全息显示、三维显示和其他信息技术。新的碳氢功能化策略的发展也将与苯并环制相结合，以提供新的和可能容易的途径来获得在吸收和发射光谱中表现出显着红移的更大的纳米石墨烯。这些活动协同为研究生、本科生和高中生提供有机合成和先进分析技术方面的培训。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis Program in the Division of Chemistry, Wesley Chalifoux of the University of Nevada, Reno is studying ways to make nanographenes from small, precise, molecular building blocks. Nanographenes are flat sheets of carbon atoms that mimic small sections of graphene. The optoelectronic properties of nanographenes make them attractive materials in applications such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic solar cells. The Chalifoux research group’s efforts to develop new ways to make these molecules are supporting the design of next-generation devices. Dr. Chalifoux and his team of students are converting modifiable chemical building blocks to nanographenes under mild conditions and monitoring how specific changes in the building blocks tune the characteristics of the nanographenes, including their three-dimensional shape and optical properties. These activities are also supporting the engagement of high school students in chemical research to encourage their engagement in science and to support their progression towards successful science, technology, engineering, and mathematics (STEM) careers.Wesley Chalifoux and his research team are advancing the use of alkyne benzannulation as a mild and versatile strategy for preparing nanographenes with tunable optical properties. The use of high-energy alkyne-containing precursors allows for the use of mild benzannulation conditions that support expanded functional group tolerance and provide access to a variety of nanographene structures that cannot be achieved using other methods. The Chalifoux group will apply this strategy to the synthesis of highly contorted and chiral nanographene molecular scaffolds that exhibit circularly polarized light characteristics and can be envisioned in variety of chiroptic applications such as liquid crystal displays, chiral sensing, holographic displays, three-dimensional displays, and other information technologies. The development of new C-H functionalization strategies will also be explored in combination with benzannulation to provide new and potentially facile routes to larger nanographenes that exhibit significant red shifts in the absorption and emission spectra. These activities are synergistically providing training in organic synthesis and advanced analytical techniques for a diverse cohort of graduate, undergraduate, and high school students.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.