The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 19
(2014) pp 275-277
Synthesis of Organic Semiconductor Backbone Using a Suzuki-Miyaura Cross-Coupling
Juha P. Heiskanen*
Department of Chemistry, P.O. Box 3000, FI-90014 University of Oulu, Finland, email@example.com
Published: 10 September 2014
Abstract. A practical undergraduate student laboratory exercise, synthesis of organic semiconductor material, quaterthiophene, using Suzuki-Miyaura cross-coupling approach is presented with detailed instructions. In this experiment, students will learn to recognize the basic needs for this class of coupling reaction, to work with inert atmosphere using a balloon technique, and to do relatively demanding recrystallization procedure. The progress of the reaction will be monitored by using thin layer chromatography (TLC) and students will learn to make conclusions when to finish the reaction. In addition, rotary evaporation, liquid-liquid extraction, and vacuum filtration techniques are recalled. The product is analyzed using 1H NMR and UV-vis spectrometers.
Key Words: Laboratories and Demonstrations; organic chemistry; synthesis; Suzuki-Miyaura cross-coupling; upper-division undergraduate laboratory exercise; material chemistry
(*) Corresponding author. (E-mail: firstname.lastname@example.org)
Further details, Reaction system, List of chemicals with GHS labels, Student guidelines of the experiment, TLC technique, 1H NMR spectrum of quaterthiophene, and UV-vis absorption spectra of both starting material and the product are presented in Supporting Materials (803 KB).