Synthesis Of Pyrazinoquinoxaline And Thiadiazoloquinoxaline-containing Monomers

A thiadiazoloquinoxline-containing monomer, 8-(7-octyl-4,9-di(thiophen-2-yl)-rn[1,2,5]thiadiazolo[3,4-g]quinoxalin-6-yl)octanoic acid (74), was designed andrnsynthesized starting from benzothiadiazole and oleic acid. An attempt was also madernto synthesize a pyrazine-containing monomer, 8,8’-(3,7-dioctyl-5,10-di(thiophen-2-rnyl)pyrazino[2,3-g]quinoxaline-2,8-diyl)dioctanoic acid (73). The syntheses of thernabove donor-acceptor based monomers involved the preparation of 9,10-diketostearicrnacid via the oxidation of oleic acid using potassium permanganate as oxidant andrncondensation of this with 4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole-5,6-diaminernand 3,6-di(thiophen-2-yl)benzene-1,2,4,5-tetraamine, respectively. In the course ofrnthis work, attempts were made to synthesize 1,2-diketones via the benzoinrncondensation of substituted benzaldehydes and the Sonogashira reaction ofrnarylbromides and 1-octyne. All intermediate compounds and products wererncharacterized by spectroscopic methods including NMR, FT-IR and UV-VIS.

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