Tuning Antiaromaticity and Diradical Properties in Diarenoindacenes, Diindenoacenes, and Related Quinoidal Scaffolds

调节二茚并苯、二茚并苯和相关醌基支架的反芳香性和双自由基性质

• 批准号: 1954389
• 负责人: Michael Haley
• 金额: $ 49万
• 依托单位: University of Oregon Eugene
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2020
• 资助国家: 美国
• 起止时间: 2020-07-01 至 2023-12-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1954389&HistoricalAwards=false
• 关键词: Tuning; Antiaromaticity; Diradical; Properties; Diarenoindacenes

With this award, the Chemical Synthesis Program of the NSF Chemistry Division is supporting the research of Professor Michael Haley of the University of Oregon who is synthesizing molecules known as indenoacenes and arenoindacenes. Professor Haley and his research group construct these compounds with systematic structural differences to answer fundamental questions about how these changes affect the electronic and material properties of these compounds. A key goal is to develop simple methods to construct these compounds in order to study their characteristics. Examination of the optical, electronic, and/or magnetic properties of these molecules then determines how they can be tuned and optimized for use in optoelectronic devices such as organic field effect transistors and organic photovoltaics. Professor Haley and his research group collaborate with material scientists, host visiting scientists from primarily undergraduate institutions for extended stays in their laboratory, and have continued substantial involvement of a diverse group of undergraduates in their research activities.Non-benzene-based conjugated systems, such as indenofluorenes (IFs), have been recognized for their potential as organic semiconductors characterized by low energy valence shells and a small band gap. This project aims to create extended IF structures and IF derivatives with heterocyclic groups to better understand the singlet-triplet gap in these diradical systems and to compare to the original IF system. The team also constructs novel asymmetric IF compounds to determine the effect of the loss of symmetry on fundamental properties. The molecules prepared in these studies present opportunities for practical applications in the areas of nanotechnology and low-cost electronics. This project also serves as an excellent training ground for graduate and undergraduate researchers with broad experiences in organic synthesis, computational chemistry, crystallography, and understanding the fundamental relationship between molecular structure and electronic properties.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.

有了这个奖项，NSF化学部的化学合成计划正在支持俄勒冈大学的迈克尔·海莉教授的研究，俄勒冈大学正在合成称为indenoacenes and arenoindacenes的分子。 Haley教授及其研究小组与系统的结构差异构建了这些化合物，以回答有关这些变化如何影响这些化合物的电子和材料特性的基本问题。一个关键目标是开发简单的方法来构建这些化合物以研究其特征。然后检查这些分子的光学，电子和/或磁性特性，确定如何对它们进行调整和优化以在光电设备中使用，例如有机场效应晶体管和有机光伏。海莉教授及其研究小组与物质科学家合作，主持了主要是本科机构的访问科学家，主要是在他们的实验室中延长的延期，并继续大量参与了多元化的本科生在其研究活动中的多样化群体。基于居民的共轭系统（例如，诸如Indenofluorenes的特征），已成为有机物（如果是有机化的），并已被列为有机化的特征。一个小带隙。该项目旨在创建扩展的IF结构以及具有异环组的衍生物，以更好地理解这些Diradical系统中的单元 - 三个差距，并与原始IF系统进行比较。 该团队还构建了新型的不对称，如果化合物确定对称损失对基本特性的影响。这些研究中准备的分子为纳米技术和低成本电子产品领域的实际应用提供了机会。该项目还为毕业和本科研究人员提供了良好的培训基础，在有机合成，计算化学，晶体学，晶体学和理解分子结构与电子特性之间的基本关系方面具有广泛的经验。该奖项反映了NSF的法定任务，并被认为是通过基金会的知识优点和广泛影响的评估来通过评估来进行评估的。

项目成果

Enhancing the Antiaromaticity of s -Indacene through Naphthothiophene Fusion

通过萘并噻吩融合增强 s-吲达苯的反芳香性

• DOI: 10.1021/acs.orglett.1c01514
• 发表时间: 2021
• 期刊: Organic Letters
• 影响因子: 5.2
• 作者: Warren, Gabrielle I.;Barker, Joshua E.;Zakharov, Lev N.;Haley, Michael M.
• 通讯作者: Haley, Michael M.

Comparison of Antiaromatic Properties in a Series of Structurally Isomeric Naphthothiophene‐Fused s ‐Indacenes

一系列结构异构萘并噻吩→稠合苯并苯的抗芳香性能比较

• DOI: 10.1002/chem.202301153
• 发表时间: 2023
• 期刊: Chemistry – A European Journal
• 作者: Warren, Gabrielle I.;Zocchi, Luca J.;Zakharov, Lev N.;Haley, Michael M.
• 通讯作者: Haley, Michael M.

OCELOT: An infrastructure for data-driven research to discover and design crystalline organic semiconductors

• DOI: 10.1063/5.0048714
• 发表时间: 2021-05-07
• 期刊: JOURNAL OF CHEMICAL PHYSICS
• 影响因子: 4.4
• 作者: Ai, Qianxiang;Bhat, Vinayak;Risko, Chad
• 通讯作者: Risko, Chad

Orbital Nature of Carboionic Monoradicals Made from Diradicals

由双自由基制成的碳离子单自由基的轨道性质

• DOI: 10.1002/chem.202300388
• 发表时间: 2023
• 期刊: Chemistry – A European Journal
• 作者: Valdivia, Abel Cardenas;Dai, Yasi;Rambaldi, Filippo;Barker, Joshua E.;Dressler, Justin J.;Zhou, Zheng;Zhu, Yikun;Wei, Zheng;Petrukhina, Marina A.;Haley, Michael M.
• 通讯作者: Haley, Michael M.