Malonic Acid Derivatives on Duty as Electron-Withdrawing Units in Push-Pull Molecules
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F17%3A39910639" target="_blank" >RIV/00216275:25310/17:39910639 - isvavai.cz</a>
Výsledek na webu
<a href="http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201700070/abstract" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201700070/abstract</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201700070" target="_blank" >10.1002/ejoc.201700070</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Malonic Acid Derivatives on Duty as Electron-Withdrawing Units in Push-Pull Molecules
Popis výsledku v původním jazyce
Based on the 2-(N-piperidinyl) thiophene central donor, 32 model push-pull molecules with systematically varied malonic acid-derived peripheral acceptors have been prepared. Further property tuning has been achieved by modifying the p-linker and the structural arrangement (linear vs. quadrupolar D-p-A systems). Malonic acid derivatives such as cyanoacetic acid, malondinitrile, diethyl malonate, Meldrum's acid, and N, N'dibutyl(thio) barbituric acid as well as 1,3-diketo analogues dimedone and indan-1,3-dione were employed as acceptor moieties. Knoevenagel condensation with four thiophene aldehydes afforded the target chromophores in satisfactory yields. The electron-withdrawing abilities of malonic acid acceptors were examined both by experiment including X-ray analysis, differential scanning calorimetry, electrochemistry, and UV/Vis absorption spectroscopy, and by DFT calculations. Details of the structure- property relationships have been elucidated. According to the increasing electron-withdrawing ability, the widely used malonic acid acceptor units can be ordered: diethyl malonate <= cyanoacetic acid < malondinitrile < Meldrum's acid < dimedone <= N, N'-dibutylbarbituric acid < indan-1,3-dione <= N, N'-dibutylthiobarbituric acid.
Název v anglickém jazyce
Malonic Acid Derivatives on Duty as Electron-Withdrawing Units in Push-Pull Molecules
Popis výsledku anglicky
Based on the 2-(N-piperidinyl) thiophene central donor, 32 model push-pull molecules with systematically varied malonic acid-derived peripheral acceptors have been prepared. Further property tuning has been achieved by modifying the p-linker and the structural arrangement (linear vs. quadrupolar D-p-A systems). Malonic acid derivatives such as cyanoacetic acid, malondinitrile, diethyl malonate, Meldrum's acid, and N, N'dibutyl(thio) barbituric acid as well as 1,3-diketo analogues dimedone and indan-1,3-dione were employed as acceptor moieties. Knoevenagel condensation with four thiophene aldehydes afforded the target chromophores in satisfactory yields. The electron-withdrawing abilities of malonic acid acceptors were examined both by experiment including X-ray analysis, differential scanning calorimetry, electrochemistry, and UV/Vis absorption spectroscopy, and by DFT calculations. Details of the structure- property relationships have been elucidated. According to the increasing electron-withdrawing ability, the widely used malonic acid acceptor units can be ordered: diethyl malonate <= cyanoacetic acid < malondinitrile < Meldrum's acid < dimedone <= N, N'-dibutylbarbituric acid < indan-1,3-dione <= N, N'-dibutylthiobarbituric acid.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2017
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
—
Svazek periodika
2017
Číslo periodika v rámci svazku
19
Stát vydavatele periodika
DE - Spolková republika Německo
Počet stran výsledku
16
Strana od-do
2764-2779
Kód UT WoS článku
000403672100012
EID výsledku v databázi Scopus
—