Collaborative Research: RUI: Manipulation of Arylene Ethynylene Structures and Properties via Coordination, Halogen Bonding and Hydrogen Bonding

美国国家科学基金会化学部的大分子、超分子和纳米化学项目支持该项目，设计和合成新的碳基分子，以潜在地用于柔性、高性能电子设备。对这些分子的研究可能会导致更好地理解如何设计所需的性能以及这些材料如何发挥作用。例如，控制共轭单体、低聚物和聚合物中的分子构象的能力不仅对于操纵它们的电子性质很重要，而且对于优化材料的体电子性质也很重要。虽然材料内的自由旋转可导致各种不可预测的且可能不期望的分子堆积布置，但用于强制平面性的策略可提供增加的有序性和增强的电子性质。因此，构象受限的亚芳基亚乙炔基是光伏、薄膜晶体管和发光器件开发中的重要目标。类似地，由于它们的刚性和可预测的几何形状，亚芳基亚乙炔基结构可以作为特定尺寸和形状的客体的主体。这些系统的几何参数的完全理解和优化可能会导致新的传感能力。负责合成和表征这些新型化合物的本科生在实验室中获得实践经验，为化学工业的职业生涯或研究生课程的额外学习做好准备。 该项目在两个不同的校园进行，威斯康星大学史蒂文斯点和密苏里州州立大学。 来自这些校区的教授参与有意义的研究，不仅提高了直接从事研究项目的学生的教育，而且也提高了从课堂上的知识和技能转移中受益的学生的教育。该项目的科学目标是设计和制备新型亚芳基乙炔结构，其特征在于允许分子水平控制电子性质，晶体设计，和主客活动。 具体而言，在共轭体系中引入吡啶基基团提供了通过卤素键合、氢键合和过渡金属配位进行结构控制的机会。 这些相互作用为产生新型液晶、增强不饱和主链的有效共轭和高度特异性的主客体配对提供了途径。

The Macromolecular, Supramolecular and Nanochemistry Program of the NSF Division of Chemistry supports this project to design and synthesize new carbon-based molecules for potential use in flexible, high performance electronic devices. The study of these molecules may lead to a better understanding of how to design desirable properties as well as how these materials function. For example, the ability to control molecular conformations in conjugated monomers, oligomers, and polymers is not only important for manipulating their electronic properties, but also for optimization of the bulk electronic properties of a material. While free rotation within a material can lead to a variety of unpredictable, and perhaps undesirable, molecular packing arrangements, strategies for enforcing planarity can provide increased order and enhanced electronic properties. Arylene ethynylenes that are conformationally constrained are, therefore, important targets in the development of photovoltaic, thin-film transistor and light emitting devices. Similarly, with their rigidity and predictable geometries, arylene ethynylene structures can serve as hosts for guests of specific sizes and shapes. Complete understanding and optimization of the geometric parameters of these systems may lead to new sensing capabilities. Undergraduates responsible for synthesizing and characterizing these novel compounds gain hands-on experience in the laboratory, preparing them for careers in chemical industry or additional study in graduate programs. This project is conducted on two different campuses, University of Wisconsin-Stevens Point and Missouri State University. The participation of professors from these campuses in meaningful research enhances the education of not only the students working directly on the research projects, but also students who benefit from the transfer of knowledge and skills in the classroom.The scientific objective of this project is to design and prepare novel arylene ethynylene structures with features that allow molecular level control over electronic properties, crystal design, and host-guest activity. Specifically, incorporation of pyridinyl groups within conjugated systems offers an opportunity for structural control via halogen bonding, hydrogen bonding, and transition metal coordination. These interactions provide avenues for the generation of novel liquid crystals, the enhanced effective conjugation of unsaturated backbones, and highly specific host-guest pairing.