Detail publikace

Thionation of lactam-containing organic pigments as a synthetic tool for near-infrared absorbing n-type semiconductors

Cigánek, M. Kratochvíl, M. Yumusak, C. Sariciftci, N. S. Krajčovič, J.

Originální název

Thionation of lactam-containing organic pigments as a synthetic tool for near-infrared absorbing n-type semiconductors

Typ

abstrakt

Jazyk

angličtina

Originální abstrakt

The diketopyrrolopyrrole derivatives (DPPs) belong to the major organic high-performance pigments finding several significant applications in diverse areas of organic electronics. The core of these derivatives is formed by a molecule with the systematic name 2,5-dihydro-pyrrolo[4,3-c]pyrrolo-1,4-dione, which offers a wide range of possible structural modifications. One of the important derivatisations is the conversion of oxygen atoms in keto groups to sulfur atoms via one-step thionation using Lawesson’s reagent. In this work, basic thiophenyl (Th-DPP) and phenyl (Ph-DPP) DPP molecules were used as starting materials for the preparation of sulfur analogues Th-DTPP and Ph-DTPP, which were subsequently subjected to a study of electronic structure, optical and semiconducting properties. Thionation brought a bathochromic shift of the solid-state absorption edge. Furthermore, the electronic structure of the studied DTPPs showed low-lying, highly stabilised LUMO orbitals (–4.5 eV), which was in good agreement with model calculations, whereas the experimental HOMO destabilisation was significantly higher than predicted (–5.6 eV). Finally, field effect mobilities were determined on a bottom-gate top-contact transistor, where thionation caused the switching of the p-type character of DPPs to the n-type character of DTPPs. Since DTPPs are still sufficiently thermally stable and have near-infrared absorption capability, low-lying LUMO and n-type mobility, they can be considered potential electron-accepting components in photovoltaics. In addition, a huge advantage is that derivatization by the thionation method represents a versatile tool for the conversion of a diverse range of organic pigments containing keto groups into their sulfur analogues.

Klíčová slova

organic photovoltaics; hydrogen-bonded pigments; diketopyrrolopyrrole; n-type semiconductors

Autoři

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

Vydáno

12. 9. 2024

Nakladatel

Vysoké učení technické v Brně, Fakulta chemická

Místo

Brno, Česká republika

Strany od

86

Strany do

86

Strany počet

1

URL

https://www.fch.vut.cz/chl/konference/program/bookofabstracts-pdf-p269547

BibTex

@misc{BUT194135,
  author="Cigánek, M. and Kratochvíl, M. and Yumusak, C. and Sariciftci, N. S. and Krajčovič, J.",
  title="Thionation of lactam-containing organic pigments as a synthetic tool for near-infrared absorbing n-type semiconductors",
  booktitle="9th Meeting on CHEMISTRY & LIFE for Sustainable Future - Book of Abstracts",
  year="2024",
  edition="první",
  pages="86--86",
  publisher="Vysoké učení technické v Brně, Fakulta chemická",
  address="Brno, Česká republika",
  url="https://www.fch.vut.cz/chl/konference/program/bookofabstracts-pdf-p269547",
  note="abstract"
}