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

J 2021

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

RICHTAR, J., M. CIGANEK, A. PROCHAZKOVA, A. KOVALENKO, H. SEELAJAROEN et. al.

Basic information

Original name

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

Authors

RICHTAR, J., M. CIGANEK, A. PROCHAZKOVA, A. KOVALENKO, H. SEELAJAROEN, M. KRATOCHVIL, M. WEITER, C. YUMUSAK, N.S. SARICIFTCI, V. LUKES and J. KRAJCOVIC

Edition

CHEMPHOTOCHEM, 2021, 2367-0932

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.679

RIV identification code

RIV/00216224:14740/21:00124511

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1002/cptc.202100127

UT WoS

000698589300001

Keywords in English

CHARGE-TRANSFERTHIN-FILMENERGYSEMICONDUCTORSDERIVATIVESSTABILITYTRANSPORTVERSATILEEMISSIONPOLYMERS

Abstract

V originále

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.

Links

90127, large research infrastructures

Name: CIISB II

Citovat

RICHTAR, J., M. CIGANEK, A. PROCHAZKOVA, A. KOVALENKO, H. SEELAJAROEN, M. KRATOCHVIL, M. WEITER, C. YUMUSAK, N.S. SARICIFTCI, V. LUKES and J. KRAJCOVIC. Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes. CHEMPHOTOCHEM. 2021, vol. 5, No 12, p. 1059-1070. ISSN 2367-0932. Available from: https://dx.doi.org/10.1002/cptc.202100127.

@article{1846464,
   author = {Richtar, J. and Ciganek, M. and Prochazkova, A. and Kovalenko, A. and Seelajaroen, H. and Kratochvil, M. and Weiter, M. and Yumusak, C. and Sariciftci, N.S. and Lukes, V. and Krajcovic, J.},
   article_number = {12},
   doi = {http://dx.doi.org/10.1002/cptc.202100127},
   keywords = {CHARGE-TRANSFERTHIN-FILMENERGYSEMICONDUCTORSDERIVATIVESSTABILITYTRANSPORTVERSATILEEMISSIONPOLYMERS},
   language = {eng},
   issn = {2367-0932},
   journal = {CHEMPHOTOCHEM},
   title = {Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes},
   url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cptc.202100127?saml_referrer},
   volume = {5},
   year = {2021}
}

TY  - JOUR
ID  - 1846464
AU  - Richtar, J. - Ciganek, M. - Prochazkova, A. - Kovalenko, A. - Seelajaroen, H. - Kratochvil, M. - Weiter, M. - Yumusak, C. - Sariciftci, N.S. - Lukes, V. - Krajcovic, J.
PY  - 2021
TI  - Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes
JF  - CHEMPHOTOCHEM
VL  - 5
IS  - 12
SP  - 1059-1070
EP  - 1059-1070
SN  - 23670932
KW  - CHARGE-TRANSFERTHIN-FILMENERGYSEMICONDUCTORSDERIVATIVESSTABILITYTRANSPORTVERSATILEEMISSIONPOLYMERS
UR  - https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cptc.202100127?saml_referrer
N2  - 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.
ER  -

RICHTAR, J., M. CIGANEK, A. PROCHAZKOVA, A. KOVALENKO, H. SEELAJAROEN, M. KRATOCHVIL, M. WEITER, C. YUMUSAK, N.S. SARICIFTCI, V. LUKES and J. KRAJCOVIC. Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes. \textit{CHEMPHOTOCHEM}. 2021, vol.~5, No~12, p.~1059-1070. ISSN~2367-0932. Available from: https://dx.doi.org/10.1002/cptc.202100127.

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