Smart Photochromic Electronic Devices: Incorporation of a Bicyclic Aziridine in Organic Semiconducting Materials

智能光致变色电子器件：在有机半导体材料中掺入双环氮丙啶

• 批准号: 2203965
• 负责人: Michael Biewer
• 金额: $ 45万
• 依托单位: University of Texas at Dallas
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2022
• 资助国家: 美国
• 起止时间: 2022-09-01 至 2025-08-31
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2203965&HistoricalAwards=false
• 关键词: Smart; Photochromic; Electronic; Devices; Incorporation

With the support of the Macromolecular, Supramolecular and Nanochemistry program in the Division of Chemistry, Michael C. Biewer of the University of Texas at Dallas is developing a photochromic unit based on aromatic molecules that contain nitrogen. The synthesized unit will be attached as a pendant group to a semiconducting organic material, which will subsequently be extended into a conjugated donor-acceptor-donor small molecule. Semiconducting materials are to be constructed based on sulfur-containing conjugated aromatic systems known as thiophenes. Supramolecular stacking of the prepared organic molecules is expected to lead to materials that can become conductive when external voltage is applied (transistor-like behavior) or light shines on them (photovoltaic cell-like behavior). A variety of synthetic manipulations will be performed in order to systematically investigate and maximize the changes in optoelectronic properties upon irradiation with light. This research has the potential to generate novel light-activated and stimuli responsive materials and polymers with potential long term applications in smart organic electronics, including display- and sensor-technology. Undergraduate and graduate students working on this project will develop a broad range of skills in organic and materials chemistry, as well as engineering. An application will be created to aid in teaching organic chemistry topics in a remote environment. The corresponding website will provide additional broader educational content and will be expanded by uploading videos on mechanistic understanding of organic reactions. Outreach and educational activities will include interactions with local high schools through Scholar’s Day events at the University of Texas at Dallas and through summer research program. At the university level, Professor Biewer will continue to direct summer exchange students from Mexican universities and educate majors throughout the school of natural sciences and mathematics on the topic of functional materials and polymers.The ability to externally modulate optoelectronic properties of pi-conjugated supramolecular assemblies and polymers, while maintaining conformational demands needed for optimal solid state-performance, is an important challenge for modern organic electronics. This project will focus on the synthetic aspects of the incorporation of a novel photochromic unit based on a bicyclic aziridine ring system into functional thiophenes. Specific objectives will concentrate on (a) the synthesis of semiconducting small organic molecules with a donor-acceptor-donor framework that contains a bicyclic aziridine unit conjugated to the thiophene core, (b) modifications of the conjugated core connected to the bicyclic aziridine unit to maximize change in mobility in photochromic states and (c) incorporation of small photochromic molecules into optoelectronic devices to create smart devices upon application of light. Organic synthetic strategies will be complemented by computational modeling. The knowledge gained will likely be applicable to the functionalization of polythiophenes and other pi-conjugated polymers, in general. The research has the potential to yield new insights into various structure-property relationships of bicyclic aziridine photoswitches and their ability to influence the electronic properties of organic electronics. Designing synthetic methods to incorporate the bicyclic aziridine unit within a conducting material, in conjunction with the electronic mobility along the backbone, may allow the creation of stimuli responsive organic materials and polymers.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.

在化学系大分子、超分子和纳米化学项目的支持下，迈克尔·C·位于达拉斯的德克萨斯大学的Biewer正在开发一种基于含氮芳香分子的光致变色单元。 合成的单元将作为侧基连接到半导体有机材料，其随后将延伸成共轭的供体-受体-供体小分子。 半导体材料是基于已知为噻吩的含硫共轭芳族体系构建的。 所制备的有机分子的超分子堆叠预计将导致当施加外部电压（晶体管样行为）或光照射在它们上（光伏电池样行为）时可以变得导电的材料。 将进行各种合成操作，以系统地研究和最大限度地提高光照射后光电性能的变化。 这项研究有可能产生新型的光激活和刺激响应材料和聚合物，在智能有机电子产品中具有潜在的长期应用，包括显示和传感器技术。 从事该项目的本科生和研究生将培养有机和材料化学以及工程方面的广泛技能。 将创建一个应用程序，以帮助在远程环境中教学有机化学主题。 相应的网站将提供更多更广泛的教育内容，并将通过上传关于有机反应机理理解的视频来扩大。 推广和教育活动将包括通过在达拉斯的得克萨斯大学的学者日活动和通过夏季研究计划与当地高中的互动。 在大学层面，Biewer教授将继续指导来自墨西哥大学的暑期交换生，并为自然科学和数学学院的专业学生提供功能材料和聚合物方面的教育。外部调节π共轭超分子组装体和聚合物光电性能的能力，同时保持最佳固态性能所需的构象要求，是现代有机电子学的一个重要挑战。 该项目将集中于将基于双环氮丙啶环系统的新型光致变色单元并入官能噻吩的合成方面。 具体目标将集中于（a）具有供体-受体-供体骨架的半导体小有机分子的合成，所述骨架含有与噻吩核共轭的双环氮丙啶单元，（B）修饰与双环氮丙啶单元连接的共轭核以使光致变色状态下的迁移率变化最大化，和（c）将小的光致变色分子结合到光电子器件中以在施加光时产生智能器件。 有机合成策略将通过计算建模得到补充。所获得的知识通常将可能适用于聚噻吩和其他π-共轭聚合物的官能化。 该研究有可能产生新的见解的各种结构-性能关系的双环氮丙啶光开关和它们的能力，影响有机电子的电子性能。 设计合成方法，将二环氮丙啶单元内的导电材料，连同电子迁移率沿着骨干，可以允许刺激响应有机材料和polymers.This奖项的创建反映了NSF的法定使命，并已被认为是值得通过评估使用基金会的智力价值和更广泛的影响审查标准的支持。