Direct Imide Formation from Thiophene Dicarboxylic Acids Gives Expanded Side-Chain Selection in Thienopyrrolediones

The synthesis of thienopyrroledione (TPD) has been updated to reduce the number of synthetic steps, remove hazardous and toxic reagents, reduce the amount of byproduct waste, and reduce the use of solvents when unnecessary. Diverse functionalization is possible, introducing 16 examples in yields from 34% to 95%. This reaction scheme was shown to be general for thiophene imides, and a more thorough exploration into side chain engineering is presented with TPD acceptors often used in organic electronic applications.