Synthesis and Evaluation of Pyrrole-Modified Porphyrins

美国国家科学基金会化学部的化学结构、动力学和机理项目支持康涅狄格大学的Christian Brueckner教授，他从中四芳基卟啉合成了吡咯修饰的卟啉，并确定了这类重要有机分子的结构/性质关系。这项工作的目标是建立卟啉环中一个吡咯亚基的结构变化（饱和度、立体体积和构象柔韧度）与基态和电子激发态（吸收和发射波长、激发态寿命）中观察到的电子性质之间的联系。结构修饰卟啉在许多技术领域都有广泛的应用，如疾病治疗、化学传感器和生物显像剂。该研究的广泛影响包括为学生提供多学科培训机会，从有机合成到光化学和光物理。合成分子的潜在应用包括用于癌症治疗的光动力治疗剂，光声成像对比度增强，以及监测混凝土中的老化过程。这些应用将通过Brueckner教授与生物医学和工程领域的研究人员的合作进行评估；这包括在英国的国际合作。本科生将通过康涅狄格大学已建立的REU项目全年参与这项研究，并且还将与当地的本科机构（中央康涅狄格州立大学）进行重大参与。

The Chemical Structure, Dynamics and Mechanisms Program in the Chemistry Division at the National Science Foundation supports Professor Christian Brueckner of the University of Connecticut, for the synthesis of pyrrole-modified porphyrins from meso-tetraarylporphyrins and the determination of structure/property relationships for this important class of organic molecule. The goal of this work is to establish connections between structural changes in one of the pyrrole sub-units of the porphyrin ring (degree of saturation, steric bulk, and conformational flexibility) and the observed electronic properties in both the ground and electronically excited states (absorption and emission wavelengths, excited state lifetimes). Structurally modified porphyrins find wide applicability in many technical fields, such as therapeutics for disease treatment, chemosensors, and biological imaging agents.Broader impacts of the research include the multidisciplinary training opportunities for students, from organic synthesis to photochemistry and photophysics. Potential applications for the synthesized molecules include photodynamic therapy agents for cancer treatment, photoacoustic imaging contrast enhancement, and monitoring the aging process in concrete. These applications will be assessed through Professor Brueckner's collaborations with researchers in the biomedical and engineering fields; this includes an international collaboration in the UK. Undergraduate participation in this research will be year-round through an established REU program at the Univeristy of Connecticut, and there is also significant involvement with a local undergraduate institution (Central Connecticut State University).