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Pyrrole-modified Porphyrins - Chromophores of Basic and Applied Interests

吡咯修饰的卟啉 - 具有基础和应用价值的发色团

基本信息

批准号：
1800361
负责人：
Christian Brueckner
金额：
$ 46.29万
依托单位：
University of Connecticut
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2018
资助国家：
美国
起止时间：
2018-08-01 至 2024-07-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1800361&HistoricalAwards=false
关键词：
Pyrrole modified Porphyrins Chromophores Basic

项目摘要

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Brueckner, a faculty member in the Department of Chemistry at the University of Connecticut. Blood is red and grass is green because of a particular class of compounds - so called porphyrins, that fulfill diverse roles throughout the living world. In addition to these natural roles, these highly colored compounds can potentially be used for a variety of "non-natural" applications that range from their use as contrast agents to improve the imaging of biological tissue for better disease detection to their use for the electrocatalytic reduction of carbon dioxide and in chemosensing efforts. With this in mind, Professor Brueckner is developing strategies to convert naturally occurring porphyrins to derivatives that possess properties the original compounds do not have. This allows them to be optimized for new applications. In addition, the derivatives being synthesized are well-suited for answering fundamental questions about the properties of the porphyrins and how those properties can be systematically altered by changes in structure. The project teaches graduate and undergraduate students in the techniques and methodologies that are used in the pharmaceutical and other industries. In this way, students are prepared to enter the workplace. Professor Brueckner's has traditionally been active in chemical education and in attracting students underrepresented in science to this most colorful research work. The multidisciplinary and very visual nature of the research make it ideal for outreach activities.The main objective of this proposal is the development of strategies to convert porphyrins into pyrrole-modified porphyrins (PMPs). PMPs are macrocycles derived from porphyrins by formally replacing at least one pyrrolic building block with a different heterocycle. Starting from synthetic porphyrins, a relatively little explored strategy will be pursued: activation of the beta-position of porphyrins, followed by ring cleavage and subsequent ring-fusion. Focus in this study is the generation of PMPs containing multiple modified pyrroles, medium-size rings, or multiple annulated ring systems. The guiding hypothesis is that these modifications result in altered electronic properties when compared to their parent compounds. The suitability of the PMPs in several biological (i.e., contrast agents in photoacoustic tissue imaging) and technical (i.e. electrocatalytic reduction of CO2, chemosensing) applications will be evaluated. The proposed work relies on collaborations with intramural and extramural (international) specialty groups in a number of biological, physical sciences and engineering disciplines. The program offers a multidisciplinary and collaborative training ground for graduate students in diverse areas ranging from organic and inorganic synthesis, physical organic chemistry, photophysics, to a number of biomedical and engineering applications. This prepares them for future careers in industry or academia. The proposal also includes year-round undergraduate research projects, and it will be part of the departmental REU program. The multidisciplinary porphyrin-related research activities are ideal for dissemination in non-technical journals and make colorful subjects of outreach activities.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.

化学部的化学合成计划支持康涅狄格大学化学系的教员Brueckner教授的项目。血是红色的，草是绿色的，这是因为有一类特殊的化合物--所谓的卟啉，在整个生命世界中扮演着不同的角色。除了这些天然作用之外，这些高度着色的化合物可以潜在地用于各种“非天然”应用，其范围从它们作为造影剂的用途以改善生物组织的成像以更好地检测疾病到它们用于二氧化碳的电催化还原和化学传感工作。考虑到这一点，Brueckner教授正在开发策略，将天然存在的卟啉转化为具有原始化合物所不具有的特性的衍生物。这使得它们能够针对新的应用进行优化。此外，正在合成的衍生物非常适合回答有关卟啉性质的基本问题，以及这些性质如何通过结构的变化而系统地改变。该项目教授研究生和本科生在制药和其他行业中使用的技术和方法。这样，学生就可以进入职场了。Brueckner教授传统上一直活跃在化学教育和吸引学生在科学代表性不足，这最丰富多彩的研究工作。该研究的多学科和非常直观的性质使其成为推广活动的理想选择。该提案的主要目标是制定将卟啉转化为吡咯修饰的卟啉（PMP）的策略。PMP是通过用不同的杂环形式上取代至少一个吡咯结构单元而衍生自卟啉的大环。从合成卟啉开始，将追求相对较少探索的策略：卟啉的β-位的活化，随后是环断裂和随后的环融合。本研究的重点是生成含有多个修饰的吡咯、中等大小的环或多个环状环系统的PMP。指导性假设是，与其母体化合物相比，这些修饰导致电子性质改变。PMP在几种生物学中的适用性（即，将评估光声组织成像中的造影剂）和技术（即CO2的电催化还原、化学传感）应用。拟议的工作依赖于与一些生物，物理科学和工程学科的校内和校外（国际）专业团体的合作。该计划为研究生提供了一个多学科和协作的培训基地，从有机和无机合成，物理有机化学，生物物理学到一些生物医学和工程应用。这为他们未来在工业或学术界的职业生涯做好了准备。该提案还包括全年的本科研究项目，它将是部门REU计划的一部分。多学科的卟啉相关研究活动非常适合在非技术期刊上传播，并使外展活动的主题丰富多彩。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。

项目成果

期刊论文数量（27）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Meso -tetra(dioxanyl)porphyrins: Neutral, low molecular weight, and chiral porphyrins with solubility in aqueous solutions

内消旋四（二恶烷基）卟啉：中性、低分子量、手性卟啉，可溶于水溶液

DOI：
10.1142/s108842462150070x
发表时间：
2021
期刊：
Journal of Porphyrins and Phthalocyanines
影响因子：
1.5
作者：
Jiang, Xu-Liang;Damunupola, Dinusha;Bruckner, Christian
通讯作者：
Bruckner, Christian

Siamese-Twin Porphyrin Goes Platinum: Group 10 Monometallic, Homobimetallic, and Heterobimetallic Complexes

DOI：
10.1021/acs.inorgchem.0c00714
发表时间：
2020-05-18
期刊：
INORGANIC CHEMISTRY
影响因子：
4.6
作者：
Dorazio, Sarina J.;Vogel, Anastasia;Meyer, Franc
通讯作者：
Meyer, Franc

Expanding the eggshell colour gamut: uroerythrin and bilirubin from tinamou (Tinamidae) eggshells

DOI：
10.1038/s41598-020-68070-7
发表时间：
2020-07-09
期刊：
SCIENTIFIC REPORTS
影响因子：
4.6
作者：
Hamchand, Randy;Hanley, Daniel;Bruckner, Christian
通讯作者：
Bruckner, Christian

Quinoline-annulated porphyrin platinum complexes as NIR emitters

喹啉环卟啉铂配合物作为近红外发射器

DOI：
10.1142/s1088424619501256
发表时间：
2020
期刊：
Journal of Porphyrins and Phthalocyanines
影响因子：
1.5
作者：
Akhigbe, Joshua;Luciano, Michael;Atoyebi, Adewole O.;Jockusch, Steffen;Brückner, Christian
通讯作者：
Brückner, Christian

S N Ar Reaction Toward the Synthesis of Fluorinated Quinolino[2,3,4‐at]porphyrins