Novel diketopyrrolopyrrole derivatives as the active material for organic electrochemical transistors

abstract

English

The diketopyrrolopyrrole (DPP) molecule, systematically named 2,5-dihydropyrrolo[4,3-c]pyrrolo-1,4-dione, belongs to the major organic high-performance pigments, which have already found several significant applications in the fields of organic electronics.1 Its structure offers an inexhaustible range of possible structural derivatizations, whereas one of the most important is the nucleophilic substitution of various alkyl chains on the nitrogen heteroatoms of the DPP core. This modification using e.g. hydrophilic side chains allows the preparation of an efficient and biocompatible p-type mixed ion-electron conductor usable for organic electrochemical transistors (OECTs).2 Our research group published the DPP modification by incorporation of bulky ethyladamantyl chains on nitrogen heteroatoms, which has brought the unique, hitherto unprecedented influence of alkyl side chains to the molecules’ arrangement.3 The resulting derivative formed herringbone aggregations leading to smaller π-π stacking distances between the conjugated cores, which resulted in ambipolar characteristics of this derivative with excellent electron mobility of 0.2 cm2 · V–1 · s–1, which is an excellent value for such modified derivatives. The current trend, which moves the importance of DPPs to an even higher level, is their application in OECTs. This is made possible by the incorporation of ethylene glycol fragments into the DPP molecule and the subsequent preparation of conjugated polymers based on such modified DPPs, as described by Krauss et al.4 They further found that the higher the ethylene glycol substituent content in the DPP-based polymer (beyond 40 wt%), the significantly higher the performance of the material in the OECT device. This kind of relatively facile derivatization opens a window of the DPP-based conjugated polymers utilization as the active materials of OECTs. Therefore, the DPP molecule is a very attractive building block for the construction of devices in the field of bioelectronics.

diketopyrrolopyrrole, organic bioelectronics, organic electrochemical transistors

Cigánek, M.; Yumusak, C.; Weiter, M.; Sariciftci, N. S.; Krajčovič, J.

12. 3. 2022

JKU LIOS

Kirchberg in Tirol, Austria

74

74

1

https://drive.jku.at/ssf/s/readFile/share/37931/2315465602876692495/publicLink/BioEl2022_Booklet.pdf