RUI: Aromatic Diimide-Stabilized Acenes, Biradicals, and Radical Ions

在这个项目中，由化学系的化学结构，动力学机制-B计划资助，Macalester学院化学系的Dennis Cao教授正在开发一种稳定分子结构的新方法。 这些结构显示出有前途的有机材料性能，但受到不稳定性的限制，这阻碍了它们的工业和医学应用。有了这些稳定的物种，将有可能开发用于可穿戴电子产品的新碳基材料以及用于医疗诊断的成像剂。该项目位于有机化学和材料化学的交界处。将进一步提供真实的研究经验，本科生在课堂和研究实验室设置。 该研究计划将在Macalester学院进行，这是一个专门的本科机构，并密切涉及本科生在科学过程的各个方面，从假设检验到结果的传播。有机实验室入门课程的研究模块的创建将吸引许多Macalester本科生，否则他们无法参与化学研究体验。该项目旨在利用邻位芳族二酰亚胺，称为mellophanic diimide，为三类不稳定的目标图案提供稳定作用：线性（氮杂）并苯，开壳双自由基物种和自由基离子。预计酰亚胺官能团的吸电子作用可防止长（氮杂）并苯中通常发生的氧化降解。 这些修改将使未来的调查，其半导体性能。将酰亚胺掺入到Clar六重体工程化芳香族化合物上预计将增强其开壳特性，这一特性可用于开发双光子吸收剂和近红外染料。阳离子基团将被利用，以增加在环境条件下的电子接受mellophanic二酰亚胺的还原态的稳定性，设置顺磁性和低能量，自由基-自由基相互作用的调查阶段。该项目的实验工作涵盖有机合成和光谱表征，并将得到计算的进一步支持。该项目的研究成果将有助于发现新的有机光学和电子材料。该奖项反映了NSF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。

In this project, funded by the Chemical Structure, Dynamic & Mechanism-B Program of the Chemistry Division, Professor Dennis Cao of the Chemistry Department at Macalester College is developing a new approach toward stabilizing molecular structures. These structures display promising organic materials properties but are limited by instabilities that prevent their industrial and medical applications. With these stabilized species, it will be possible to develop new carbon-based materials for use in wearable electronics as well as imaging agents for medical diagnosis. The project, which lies at the interface of organic and materials chemistry. will further provide authentic research experiences to undergraduate students in both classroom and research laboratory settings. The research program will take place at Macalester College, an exclusively undergraduate institution, and closely involve undergraduate students in all aspects of the scientific process, ranging from hypothesis testing to the dissemination of results. The creation of research modules for introductory organic laboratory courses will engage many Macalester undergraduates who otherwise could not participate in a chemistry research experience.This project seeks to exploit an ortho-aromatic diimide, known as mellophanic diimide, to provide stabilizing effects to three classes of unstable target motifs: linear (aza)acenes, open-shell biradical species, and radical ions. The electron withdrawing effect of the imide functional group is expected to prevent oxidative degradation that normally takes place in long (aza)acenes. These modifications will enable future investigations into their semiconducting properties. The incorporation of imides onto Clar sextet engineered aromatic compounds is anticipated to enhance their open-shell character, a feature that can be exploited in the development of two-photon absorbers and near-IR dyes. Cationic groups will be leveraged to increase the stability of the reduced states of the electron accepting mellophanic diimide under ambient conditions, setting the stage for paramagnetic and low-energy, radical-radical interaction investigations. The experimental work in the project spans organic synthesis and spectroscopic characterization and will be further supported by computations. It is expected that the findings of this project will facilitate the discovery of new organic optical and electronic materials.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.