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

https://doi.org/10.1002/cptc.202100127

UT WoS

000698589300001

EID Scopus

2-s2.0-85115370394

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://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 = {https://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://doi.org/10.1002/cptc.202100127.

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