Synthesis of Organic Semiconductor Backbone Using a Suzuki-Miyaura Cross-Coupling

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

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, juha.heiskanen@oulu.fi
Received February 13, 2014. Accepted August 21, 2014.

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: jhouse@iwu.edu )

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Supporting Materials:

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).