Publication detail

Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

RICHTÁR, J. CIGÁNEK, M. JANČÍK PROCHÁZKOVÁ, A. KOVALENKO, A. SEELAJAROEN, H. KRATOCHVÍL, M. WEITER, M. YUMUSAK, C. SARICIFTCI, N. LUKEŠ, V. KRAJČOVIČ, J.

Original Title

Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

Type

journal article in Web of Science

Language

English

Original Abstract

The synthesis, experimental and theoretical study of the novel air-stable four adamantane-bearing dyes based on the trans-epindolidione (EPI) and trans-quinacridone (QA) cores are presented. Compared to the parent EPI and QA, the methyl-/ethyladamantyl substitution ensures that their structural stability in crystals is preserved due to the self-organizing properties of adamantyl groups. The investigated materials are solution-processable in common organic solvents and possess excellent thermal stability. The very good solubility was achieved by a one-step short and easy synthesis, which resulted in moderate yields of a new family of synthesized dyes. The ethyladamantyl EPI derivative (3) exhibits a unique rise in thermal stability reaching 412 degrees C. The resulting electrochemical band gap carried out on thin-film evaporated on ITO-coated glass electrodes was in the range of 2.4-2.5 eV. The experimental HOMO energies range from -6.2 to -6.0 eV, and LUMO energies lay between -3.7 and -3.5 eV. The prepared compounds are characterized by strong fluorescence in solutions and in powder, suggesting a decrease in the extent of non-radiative relaxation processes.

Keywords

Molecular designing; Adamantyl induced packing; Organic pigments; UV-Vis spectroscopy; Fluorescence

Authors

RICHTÁR, J.; CIGÁNEK, M.; JANČÍK PROCHÁZKOVÁ, A.; KOVALENKO, A.; SEELAJAROEN, H.; KRATOCHVÍL, M.; WEITER, M.; YUMUSAK, C.; SARICIFTCI, N.; LUKEŠ, V.; KRAJČOVIČ, J.

Released

14. 9. 2021

Publisher

WILEY-V C H VERLAG GMBH

Location

WEINHEIM

ISBN

2367-0932

Periodical

ChemPhotoChem

Year of study

5

Number

12

State

Federal Republic of Germany

Pages from

1059

Pages to

1070

Pages count

11

URL

https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202100127

BibTex

@article{BUT173002,
  author="RICHTÁR, J. and CIGÁNEK, M. and JANČÍK PROCHÁZKOVÁ, A. and KOVALENKO, A. and SEELAJAROEN, H. and KRATOCHVÍL, M. and WEITER, M. and YUMUSAK, C. and SARICIFTCI, N. and LUKEŠ, V. and KRAJČOVIČ, J.",
  title="Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes",
  journal="ChemPhotoChem",
  year="2021",
  volume="5",
  number="12",
  pages="1059--1070",
  doi="10.1002/cptc.202100127",
  issn="2367-0932",
  url="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202100127"
}