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Small Heterocyclic D-pi-D-pi-A Push-Pull Molecules with Complex Electron Donors
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: European Journal of Organic Chemistry
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 3223-3233
Titles:
Language Name Abstract Keywords
cze Malé heterocyklické D-pi-D-pi-A push-pull Molekuly s komplexními elektron donory 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. DFT kalkulace; heteroaromatické donory; N,N'-dibutyl-2-thiobarbiturová kyseina; optoelectronické vlastnosti; push-pull chromofory
eng Small Heterocyclic D-pi-D-pi-A Push-Pull Molecules with Complex Electron Donors 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. DFT calculations; Heteroaromatic donors; N; N'-dibutyl-2-thiobarbituric acid; Optoelectronic properties; Small push-pull chromophores

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