Synthesis, analysis, and application of azo-dyes: An organic chemistry or joint organic/physical chemistry experiment

CHED 235

Mark Schneider, mschneider@mail.widener.edu1, Loyd D. Bastin, bastin@pop1.science.widener.edu1, Ismail Kul, ikul@mail.widener.edu2, and Jim Patterson, jpatterson@sccd.ctc.edu3. (1) Department of Chemistry, Widener University, One University Place, Chester, PA 19013-5792, (2) Department of Chemistry & Biochemistry, Widener University, One University Place, Chester, PA 19013, (3) Department of Chemistry, North Seattle Community College, Seattle, WA 98103
Here we describe an undergraduate laboratory experiment designed to foster collaboration between organic laboratory students and/or organic and physical chemistry laboratory students. The experiment involves the synthesis of an azo-dye from a 13 compound library of aromatic amines and activated aromatic compounds by the organic laboratory students. Once the dye has been synthesized, it is characterized in neutral, acidic, and basic conditions by UV-Vis spectroscopy. The experimental UV-Vis spectroscopic data is compared to theoretical values obtained by the physical chemistry students using Spartan '04. The azo-dye is then used to dye a 13 piece fabric that is chemically analyzed by the students. The azo-dye is then used to attempt the dyeing of KH2PO4 (KDP) Crystals. Here we present a summary of the student results obtained from a variety of students in different courses (Allied Health Organic/Biochemistry, Organic Chemistry, and Honors Organic Chemistry) at various institutions (the University of Washington, Antioch College, Claremont McKenna College, Pitzer College, Scripps College, North Seattle Community College, and Widener University).