Imine Coupling Between Thienothiophene and Benzothiadiazole Derivative for Optoelectronic Properties

The synthesis of (E)-N-(benzo[c][1,2,5]thiadiazol-4-yl)-1-(3-nonylthieno[3,2-b]th iophen-2-yl)methanimine through coupling between 4-amino-2,1,3-benzothiadiazole and 3-nonylthieno[3,2-b]thiophene-2-carbaldehyde through a series of synthetic routes from functionalisation of the primers of the reactants in a bid to investigate stable Schiff-base benzothiadiazole molecule for opto-electronic applications. A single coupling was successfully achieved from preliminary studies in the 4-amino position of the acceptor molecule and 2-carbaldehyde position of the donor molecule to produce an imine bridge which was however characterised by low stability as it degraded afterwards upon exposure to mild light. Thus, such mechanistic approach suggests unsuitability for obtaining opto-electronic compounds. Para amination was not successful and thus symmetrical D-A-D optoelectronic compound was not achieved.