RUI: Carbaporphyrins, Neo-Confused Porphyrins and Related Systems

本研究由化学系化学合成研究计划资助，Timothy D.伊利诺斯州州立大学化学系的Lash将探索卟啉类大环化合物的合成、表征和反应性，包括新混乱的卟啉和其他碳卟啉系统。 具体而言，杂苯并卟啉和杂吡啶卟啉的合成将使用“3 + 1”策略开发。 以前制备的monocarbaporphyrins的化学也将进行研究。 本论文还将研究由环戊烯二醛合成碳卟啉和氨甲酰氯的方法以及由6-甲氧基甘菊环合成苯并碳卟啉的新途径。 将研究合成一类新的卟啉异构体（称为新混淆卟啉）的一般方法。 除了二碳卟啉，三或四碳卟啉系统将进行研究。这项工作不仅会导致更有效的路线carbaporphyrinoid系统，但也将允许获得新类别的卟啉类似物。 这个项目对提高我们对基本化学概念如芳香性的基本理解很重要。 它还具有精细化学品合成的实际应用，因为目标化合物可用于构建化学合成的催化剂。 此外，目标化合物在药物中是重要的，因为它们在光动力治疗中具有潜在的应用。 这些项目不仅为培养有机合成领域的本科生和硕士研究生提供了良好的环境，而且还使他们接触到现代科学研究的多学科性质。

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Timothy D. Lash of the Department of Chemistry at Illinois State University will explore the synthesis, characterization, and reactivity of porphyrin-like macrocycles, including neo-confused porphyrins and other carbaporphyrinoid systems. Specifically, syntheses of heterobenziporphyrins and heteropyriporphyrins will be developed using a "3 + 1" strategy. The chemistry of previously prepared monocarbaporphyrins will also be studied. A strategy for synthesizing carbaporphyrins and carbachlorins from a cyclopentene dialdehyde and a new route to benzocarbaporphyrins from 6-methoxyazulene will be developed. General approaches to the synthesis of a new class of porphyrin isomers known as neo-confused porphyrins will be investigated. In addition to dicarbaporphyrinoids, tri- or tetracarbaporphyrinoid systems will be studied.This work will not only lead to more efficient routes to carbaporphyrinoid systems but will also allow access to new classes of porphyrin analogues. This project is important to improve our basic understanding of fundamental chemistry concepts such as aromaticity. It also has practical applications for the synthesis of fine chemicals, since the target compounds can be used to construct catalysts for chemical synthesis. In addition, the target compounds are important in medicines, as they have potential applications in photodynamic therapy. These projects not only provide an excellent environment for training undergraduates and master level graduate students in the field of organic synthesis, but they also expose them to the multidisciplinary nature of modern scientific research.