Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes: Chemistry and Fluorescent Properties.

Independent of the substrate structure and reaction conditions, 3-amino-2-cyanothioacrylamides, which contain two active electrophilic centers, were shown to interact with various active halo methylene compounds under mild conditions to afford 5-acyl-2-amino-3-cyanothiophenes as the only products. A series of new polyfunctional thiophene derivatives with a rare combination of functionalities were synthesized, and their photophysical properties were experimentally and computationally investigated. The calculated electronic characteristics of the ground and excited states were compared to the experimental results, which provided a good understanding of the relationship between the optoelectronic properties and the molecular structures. After absorption of light quanta, the systems populate an intramolecular charge-transfer (ICT) Franck-Condon state, and emission occurs from a twisted ICT minimum.