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 structures may lead to a better understanding of how to design desirable properties as well as how these materials function. 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.<br/><br/>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 1) the generation of novel liquid crystals, 2) the enhanced effective conjugation of unsaturated backbones, and 3) highly specific host-guest pairing.