Publication detail

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

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

Original Title

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

English Title

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

Type

journal article in Web of Science

Language

en

Original Abstract

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.

English abstract

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.

Keywords

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

Released

13.04.2017

Pages from

1

Pages to

10

Pages count

10

URL

Documents

BibTex


@article{BUT135191,
  author="Alexander {Kovalenko} and Patricie {Heinrichová} and Stanislav {Stříteský} and Martin {Vala} and Martin {Weiter} and Jozef {Krajčovič}",
  title="Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials",
  annote="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.",
  chapter="135191",
  doi="10.1039/C6TC05076J",
  howpublished="online",
  number="19",
  volume="5",
  year="2017",
  month="april",
  pages="1--10",
  type="journal article in Web of Science"
}