Aiming at developing high performance organic semiconducting materials for organic field effect transistors (OFETs), organic photovoltaics (OPVs), printable electronics, and sensors, we have designed and synthesized a few novel semiconductors in terms of Bay-annulated-indigo (BAI), thienoazacoronene (TAC) and diketopiperazine (DKP), with amide group as the functionalizing and derivation group. By aromatic annulation at the bay position of the natural inspired dye indigo, a novel acceptor (BAI) was developed. BAI based conjugated polymers showed high performance in OFET devices, with hole and electron mobilities up to 1.5 and 0.41 cm2 V−1 s−1, respectively. A regioselective synthesis of an azacoronene fused with two peripheral thiophene groups has been realized through a concise synthetic route. The resulting thienoazacoronene (TAC) derivatives show high degree of self-organization in solution, in single crystals, in the bulk, and in spun-cast thin films. Organic photovoltaic devices using TAC-containing conjugated polymers as the donor material exhibited a high open-circuit voltage of 0.89 V, which was ascribable to TAC’s low-lying highest occupied molecular orbital energy level. Diketopiperazine shows high reactivity with aromatic aldehydes and ketones in name of Adol condensation, resulting in interesting amide based building blocks for construction of organic semiconductors. Furthermore, this chemistry has been successfully utilized for metal free synthesis of hydrogen bonding involved conjugated polymers, opening the door to a new family of organic electronic materials.

Amide chemistry towards novel, high-performance organic semiconductors

251st National Meeting (2016)

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