Publication detail

Complete Set of Diketopyrrolopyrrole Centrosymmetrical Cofacial Stacked Pairs

LUŇÁK, S. WEITER, M. VALA, M.

Original Title

Complete Set of Diketopyrrolopyrrole Centrosymmetrical Cofacial Stacked Pairs

Type

journal article in Web of Science

Language

English

Original Abstract

Stacked centrosymmetrical dimers and simultaneously H-bonded and stacked hexamers of thiophene-substituted diketopyrrolopyrrole (ThDPP) were studied using DFT as models for crystals with slipped-stacked molecules in 1D columns. Eight stacked dimer arrangements were found, six of which are driven by the minimisation of electron repulsion and realised by placing the partially negatively charged atoms of the diketopyrrolopyrrole rings below the centre of an adjacent thiophene ring. Four of these stacks are related to N,N'-dialkylated derivatives of ThDPP found in the literature, while a further one is related to an N,N'-diacylated derivative. An analogous set of eight stacks was discovered computationally for phenyl-substituted DPP (PhDPP), four of which are known among H-bonded DPP pigments, and one more among N,N'-dialkylated PhDPP derivatives. The results shed more light on the mechanisms that drive the formation of stacks between nonaromatic (DPP) and aromatic (Th, Ph) rings. The excitation energies of the lowest four singlet states computed by TD DFT enabled excitonic coupling and energy separation between Frenkel-resonance-type and charge-transfer states to be established, depending on the equilibrium stack geometry.

Keywords

diketopyrrolopyrrole; stacked centrosymmetrical dimers; excitonic coupling; density functional calculations; crystal engineering

Authors

LUŇÁK, S.; WEITER, M.; VALA, M.

Released

30. 6. 2022

Publisher

WILEY-V C H VERLAG GMBH

Location

WEINHEIM

ISBN

1439-4235

Periodical

CHEMPHYSCHEM

Year of study

23

Number

21

State

Federal Republic of Germany

Pages count

9

URL

https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cphc.202200252

BibTex

@article{BUT181373,
  author="Stanislav {Luňák} and Martin {Weiter} and Martin {Vala}",
  title="Complete Set of Diketopyrrolopyrrole Centrosymmetrical Cofacial Stacked Pairs",
  journal="CHEMPHYSCHEM",
  year="2022",
  volume="23",
  number="21",
  pages="9",
  doi="10.1002/cphc.202200252",
  issn="1439-4235",
  url="https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cphc.202200252"
}