Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials

Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials

Článek WoS

Novel ethyladamantylsolubilization side groups were found to induce pi-pi interactions between the conjugated cores through adamantyl–adamantyl stacking in soluble diketopyrrolopyrrole (DPP) derivatives. The closeness of the DPP cores amplifies charge transfer in the material,as far as pi-pi interaction is a dominant charge-hopping pathway. As a result, tenfold enhancement of hole mobilities exceeding those obtained for insoluble derivativeswasreached. Moreover, due to high crystallinity and co-planarity of the conjugated cores, electron transfer was preserved with a mobility of 0.2 cm2/(Vs)for dithiophene-DPP. At the same time, the material remained soluble, which is a significant advantage for purification and processing. This approach can be universally applied for many types of semiconducting organic materials containingtheimide motive, where solubilization is achieved by side-group substitution. Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials.

Novel ethyladamantylsolubilization side groups were found to induce pi-pi interactions between the conjugated cores through adamantyl–adamantyl stacking in soluble diketopyrrolopyrrole (DPP) derivatives. The closeness of the DPP cores amplifies charge transfer in the material,as far as pi-pi interaction is a dominant charge-hopping pathway. As a result, tenfold enhancement of hole mobilities exceeding those obtained for insoluble derivativeswasreached. Moreover, due to high crystallinity and co-planarity of the conjugated cores, electron transfer was preserved with a mobility of 0.2 cm2/(Vs)for dithiophene-DPP. At the same time, the material remained soluble, which is a significant advantage for purification and processing. This approach can be universally applied for many types of semiconducting organic materials containingtheimide motive, where solubilization is achieved by side-group substitution. Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials.

diketopyrrolopyrrole, side-chain engineering, OFET, ambipolarity, field-effectmobility

diketopyrrolopyrrole, side-chain engineering, OFET, ambipolarity, field-effectmobility

Alexander Kovalenko, Cigdem Yumusak, Patricie Heinrichova, Stanislav Stritesky, Ladislav Fekete, Martin Vala, Martin Weiter, Niyazi Serdar Sariciftci and Jozef Krajcovic

2018

13.04.2017

2050-7534

Journal of Materials Chemistry C

5

19

Spojené království Velké Británie a Severního Irska

1

10

10

https://pubs.rsc.org/en/content/articlelanding/2017/tc/c6tc05076j#!divAbstract

Zduvodneni_JK_2019
J. Mater. Chem. C, 2017, 5, 4716-4723