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Xavier大学（XULA）化学系的Jayalakshmi Sridhar和Kevin Riley探索了新发现的合成方法的多功能性，以创建具有有趣特性的二聚体醌分子。这项研究的目的是将创建设计的二聚体奎因酮的直接方法标准化，该方法在有效的能量存储系统（例如氧化还原流量电池）中具有强大的潜力，为着色剂（染料）和药物应用（例如，用于此类疾病的治疗方法作为癌症和致病感染）。该项目位于有机，计算，材料和药物化学的界面。因此，该项目非常适合培训多个化学领域的本科生。协作研究小组在培训有机合成技术和计算化学工具的少数群体学生方面经验丰富。这些研究小组在为科学领域不足的学生提供最高水平的研究培训方面，并确保他们在研究生院的成功。这些学生接受了化学实验室科学探索的培训，在国家会议上以口头和书面格式的结果进行交流，并增强对在科学职业中取得成功至关重要的软技能。 同型和异二聚体喹酮属于一类重要的分子，这些分子在储能，药物和染料的区域中具有多个应用。二聚体奎因酮能够螯合多种金属阳离子，并具有增强的氧化还原流动电池性能。这些扩展的共轭系统显示基于pH的颜色光谱。在几种生物活性天然产物中发现的喹酮核心部分可与针对特定生物分子的修饰。新鉴定的合成方法始于经历氧化还原反应的Diels-Alder产品，并增加了形成二聚体奎因酮的迈克尔。该反应将用于提供一种可预测且易于自适应的方式来创建各种均型和异喹酮二聚体。在该项目中，新合成方法的以下方面是针对研究的。 （1）将使用计算和合成方法研究反应的机理，目的是将合成方案开发到具有特定结构特征的设计喹酮二聚体中。 （2）随着机械洞察力获得的，团队将探索具有各种结构特征在内的均应二聚体的合成，包括杂环支架； （3）同样，协作的Sridhar/Riley团队将研究为特定最终用途而设计的异二聚体的反应的多功能性。该奖项反映了NSF的法定任务，并被认为是值得通过基金会的评估来支持的。智力优点和更广泛的影响审查标准。