Zobrazit minimální záznam
dc.contributor.author |
Kulhánek, Jiří
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dc.contributor.author |
Pytela, Oldřich
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|
dc.contributor.author |
Bureš, Filip
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dc.contributor.author |
Klikar, Milan
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dc.date.accessioned |
2022-06-03T12:26:15Z |
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dc.date.available |
2022-06-03T12:26:15Z |
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dc.date.issued |
2021 |
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dc.identifier.issn |
1434-193X |
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dc.identifier.uri |
https://hdl.handle.net/10195/79259 |
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dc.description.abstract |
A large series of small push-pull chromophores based on electron-withdrawing N,N'-dibutylthiobarbituric acid has been designed and successfully synthesized. The electron donating part involves common mesomeric donors such as methoxy, N,N-dimethylamino, N,N-diphenylamino, and piperidin-1-yl groups. Five-membered heteroaromatics, namely thiophene, N-methylpyrrole, and furan have been employed as electron rich pi-linkers and auxiliary donors. Structural analogues bearing aromatic 1,4-phenylene linker were also synthesized for comparison. Fundamental thermal and optoelectronic properties were studied by differential scanning calorimetry, cyclic voltammetry, and absorption spectroscopy. Thorough structure-property relationships were elucidated, focusing mostly on type of the used pi-linker and donor. All experimental conclusions are corroborated by theoretical calculations. The study has shown that a complex donor moiety may be built by properly combining mesomeric and auxiliary donors. Whereas strong mesomeric donor (amino) suppresses the donating effect of auxiliary donors/pi-linkers, a combination of weak donor (methoxy) appended at a five-membered heterocycle pronounces the donating ability of the latter. |
eng |
dc.format |
p. 3223-3233 |
eng |
dc.language.iso |
eng |
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dc.publisher |
Wiley-VCH |
eng |
dc.relation.ispartof |
European Journal of Organic Chemistry, volume 2021, issue: 22 |
eng |
dc.rights |
Článek ve verzi „published“ je přístupný pouze v rámci univerzity. |
cze |
dc.subject |
DFT calculations |
eng |
dc.subject |
heteroaromatic donors |
eng |
dc.subject |
N |
eng |
dc.subject |
N'-dibutyl-2-thiobarbituric acid |
eng |
dc.subject |
optoelectronic properties |
eng |
dc.subject |
small push-pull chromophores |
eng |
dc.subject |
DFT kalkulace |
cze |
dc.subject |
heteroaromatické donory |
cze |
dc.subject |
N'-dibutyl-2-thiobarbiturová kyselina |
cze |
dc.subject |
optoelectronické vlastnosti |
cze |
dc.subject |
push-pull chromofory |
cze |
dc.title |
Small Heterocyclic D-π-D-π-A Push-Pull Molecules with Complex Electron Donors |
eng |
dc.title.alternative |
Malé heterocyklické D-π-D-π-A push-pull Molekuly s komplexními elektron donory |
cze |
dc.type |
article |
eng |
dc.description.abstract-translated |
Byla úspěšně připravena velká série malých push-pull chromorofů na bázi elektronakceptorní N,N'-dibutylthiobarbiturové kyseliny. Elektrondonorní část molekul obsahovala běžné mezomerní donory jako methoxy, N,N-dimethylamino, N,N-difenylamino a piperidin-1-yl skupinu. Jako pi-linker a podpůrný donor byly využity pětičlenné heteroaromáty thiofen, N-methylpyrrol a furan. Pro srovnání byly připraveny také strukturní analogy nesoucí aromatický 1,4-fenylenový linker. Byly studovány termální a optoelektronické vlastnosti pomocí DSC, cyklické voltametrie a absorpční spektroskopie. |
cze |
dc.peerreviewed |
yes |
eng |
dc.publicationstatus |
published version |
eng |
dc.identifier.doi |
10.1002/ejoc.202100137 |
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dc.relation.publisherversion |
https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202100137 |
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dc.identifier.wos |
000664610800010 |
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dc.identifier.scopus |
2-s2.0-85108329794 |
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dc.identifier.obd |
39886140 |
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