Achiral and Chiral Nanographene Synthesis Using an Alkyne Linchpin Strategy

在内华达大学化学系化学合成计划的支持下，雷诺正在研究如何从微小的、精确的分子构件中制造纳米分子。纳米石墨烯是碳原子的扁平片，模仿石墨烯的小部分。纳米薄膜的光电性质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领域具有广泛的应用前景。Chalifoux研究小组努力开发制造这些分子的新方法，这为下一代设备的设计提供了支持。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图形，并监测构建块中的特定变化如何调整纳米图形的特性，包括它们的三维形状和光学性质。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研究，并支持他们走向成功的科学、技术、工程和数学(STEM)职业生涯。Wesley Chalifoux和他的研究团队正在推动将炔苯环化作为一种温和而通用的策略来制备具有可调光学性质的纳米图形。使用高能的含炔前驱体允许使用温和的苯环化条件，该条件支持扩大的官能团容忍度，并提供使用其他方法无法实现的各种纳米茂烯结构的途径。Chalifoux团队将把这一策略应用于合成高度扭曲和手性的纳米分子支架，这种支架具有圆偏振光特性，可用于各种手性应用，如液晶显示器、手性传感、全息显示器、三维显示器和其他信息技术。新的C-H官能化策略的开发也将与苯环化相结合，以提供新的、潜在的容易获得在吸收和发射光谱中表现出显著红移的较大纳米烯的路线。这些活动协同为不同的研究生、本科生和高中生提供有机合成和高级分析技术方面的培训。该奖项反映了NSF的法定使命，并通过使用基金会的智力优势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.