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.

Základní údaje

Originální název

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

Autoři

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

Vydání

CHEMPHOTOCHEM, 2021, 2367-0932

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.679

Kód RIV

RIV/00216224:14740/21:00124511

Organizační jednotka

Středoevropský technologický institut

DOI

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

UT WoS

000698589300001

Klíčová slova anglicky

CHARGE-TRANSFERTHIN-FILMENERGYSEMICONDUCTORSDERIVATIVESSTABILITYTRANSPORTVERSATILEEMISSIONPOLYMERS

Štítky

CF SAXS, ne MU, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 18. 5. 2022 15:01, Mgr. Pavla Foltynová, Ph.D.

Anotace

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.

Návaznosti

90127, velká výzkumná infrastruktura

Název: CIISB II

Citovat

RICHTAR, J., M. CIGANEK, A. PROCHAZKOVA, A. KOVALENKO, H. SEELAJAROEN, M. KRATOCHVIL, M. WEITER, C. YUMUSAK, N.S. SARICIFTCI, V. LUKES a J. KRAJCOVIC. Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes. CHEMPHOTOCHEM. 2021, roč. 5, č. 12, s. 1059-1070. ISSN 2367-0932. Dostupné z: 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 a J. KRAJCOVIC. Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes. \textit{CHEMPHOTOCHEM}. 2021, roč.~5, č.~12, s.~1059-1070. ISSN~2367-0932. Dostupné z: https://dx.doi.org/10.1002/cptc.202100127.

Podrobný výpis o publikaci