Malonic Acid Derivatives on Duty as Electron-Withdrawing Units in Push-Pull Molecules

Result code in 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>
Result on the web
<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>

Result language
angličtina
Original language name
Malonic Acid Derivatives on Duty as Electron-Withdrawing Units in Push-Pull Molecules
Original language description
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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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