Research-Focused Approach for Introducing Undergraduate Students to Aromatic Organic Synthesis at a Community College

• Jessica T. Boette ^[1] ; Kira M. Daniel ^[1] ; Josephine W. Lietzke ^[1] ; Shawn M. Amorde ^[1] ; Sean T. Roberts ^[2]
  1. [1] Austin Community College

     Austin Community College

     Estados Unidos

     
  2. [2] University of Texas at Austin

     University of Texas at Austin

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 100, Nº 2, 2023, págs. 572-580
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • The addition of research-focused experiences to undergraduate chemistry laboratory courses has been shown to bolster student learning, enhance student retention in STEM, and improve student self-identity as scientists. In the area of synthetic organic chemistry, the preparation of libraries of compounds with novel optical and electronic properties can provide a natural motivational goal for research-focused exercises that can be undertaken by individual students or collectively as a class. However, integrating such experiences into a community college teaching laboratory setting can face challenges imposed by the cost of supplies, limited laboratory space, and access to characterization facilities. To address these challenges, we have devised a sequence of inquiry-driven, research-focused laboratory exercises that can be readily integrated into an organic chemistry laboratory course with minimal cost. This sequence consists of a multistep synthesis of perylenediimide dyes that introduces students to advanced synthetic techniques, such as organometallic coupling reactions, column purification, and reactions performed under inert atmosphere. This high-yield, three-part synthesis can be easily varied by individual students or small groups within a class to form a broad library of compounds with potential utility for applications in light harvesting, molecular electronics, catalysis, and medicine. We describe the design of low-cost workstations for chemical synthesis under inert atmosphere and provide auxiliary lesson plans that can be used to expand the scope of a laboratory course beyond synthetic organic chemistry by introducing students to concepts in molecular spectroscopy.