Excellence in Research- Dimeric Bis-Naphthoquinone Formation via a Green and Straightforward Approach Mechanistic and Adaptability Studies

卓越的研究 - 通过绿色和直接的方法形成二聚双萘醌机制和适应性研究

• 批准号: 2300447
• 负责人: Jayalakshmi Sridhar
• 金额: $ 45.36万
• 依托单位: Xavier University of Louisiana
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2023
• 资助国家: 美国
• 起止时间: 2023-08-15 至 2026-07-31
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2300447&HistoricalAwards=false
• 关键词: Excellence; Research; Dimeric; Bis; Naphthoquinone

In this Excellence in Research project, Jayalakshmi Sridhar and Kevin Riley of the Department of Chemistry at Xavier University of Louisiana (XULA) explore the versatility of a newly discovered synthetic method for creation of dimeric quinone molecules with interesting properties. The goal of this research is to standardize the straightforward method for creation of designed dimeric quinones, which have strong potential in efficient energy storage systems (e.g. redox flow batteries), as coloring agents (dyes) and in pharmaceutical applications (e.g. therapeutics for diseases such as cancer and pathogenic infections). The project lies at the interface of organic, computational, materials and medicinal chemistry. Therefore, the project is well suited to train undergraduate students in multiple areas of chemistry. The collaborative research groups are well experienced in training undergraduate minority students in organic synthetic techniques and computational chemistry tools. The research groups are well positioned to provide the highest level of research training for students underrepresented in science and ensure their success in graduate schools. The students receive training in scientific explorations in chemistry labs, communication of results in oral and written formats at national conferences and enhancement of soft skills essential for succeeding in a scientific career. Homo- and heterodimeric quinones belong to an important class of molecules that have multiple applications in the areas of energy storage, pharmaceuticals and dyes. Dimeric quinones are capable of chelating to multiple metal cations with enhanced performance in redox flow batteries. These extended conjugated systems display pH-based color spectra. The quinone core moiety, found in several biologically active natural products, is amenable to modifications for targeting specific biomolecules. The newly identified synthetic method begins with Diels-Alder products undergoing redox reactions and Michael addition to form dimeric quinones. This reaction will be explored for its use in providing a predictable and easily adaptable way to create a wide array of homo- and hetero-bisquinone dimers. In this project, the following aspects of the new synthetic method are targeted for study. (1) The mechanism of the reaction will be studied using computational and synthetic methods with the goal of developing synthetic protocols into designed quinone dimers with specific structural features. (2) With the mechanistic insight gained, the team will explore the synthesis of homodimers with varied structural features including heterocyclic scaffolds; and (3) Similarly, the collaborative Sridhar/Riley team will examine the versatility of the reaction for the synthesis of heterodimers that are designed for specific end uses.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.

在这个卓越的研究项目中，路易斯安那州泽维尔大学（Xavier University of Louisiana）化学系的Jayalakshmi Sridhar和Kevin Riley探索了一种新发现的合成方法的多功能性，用于创造具有有趣特性的二聚醌分子。这项研究的目标是标准化用于创建设计的二聚醌的简单方法，这些二聚醌在有效的能量存储系统（例如氧化还原液流电池）中具有强大的潜力，作为着色剂（染料）和药物应用（例如癌症和病原性感染等疾病的治疗剂）。该项目位于有机，计算，材料和药物化学的界面。因此，该项目非常适合培养化学多个领域的本科生。合作研究小组在培训本科少数民族学生有机合成技术和计算化学工具方面经验丰富。研究小组有能力为科学领域代表性不足的学生提供最高水平的研究培训，并确保他们在研究生院取得成功。学生接受化学实验室的科学探索培训，在全国会议上以口头和书面形式交流结果，并提高在科学事业中取得成功所必需的软技能。 同二聚体和异二聚体醌属于一类重要的分子，其在能量储存、药物和染料领域中具有多种应用。二聚醌能够螯合多种金属阳离子，在氧化还原液流电池中具有增强的性能。这些扩展的共轭系统显示基于pH的颜色光谱。醌核心部分，发现在几个生物活性的天然产品，是适合于针对特定的生物分子的修改。新确定的合成方法开始与Diels-Alder产品进行氧化还原反应和迈克尔加成形成二聚醌。该反应将探索其在提供可预测的和容易适应的方式来创建一个广泛的同和杂双醌二聚体的使用。本项目主要从以下几个方面对新的合成方法进行了研究。(1)该反应的机理将使用计算和合成方法进行研究，目标是将合成方案开发成具有特定结构特征的设计醌二聚体。(2)随着机械的洞察力，该团队将探索合成具有不同结构特征的同源二聚体，包括杂环支架;（3）同样，合作的Sridhar/Riley团队将考察该反应的多功能性，用于合成为特定最终用途设计的异二聚体。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。