About: Electrochemical and Quantum Chemical Investigation of Tetranitrocalix[4]arenes: Molecules with Multiple Redox Centers

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An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1021/jo4015613
Description	The calix[4]arene skeleton is electrochemically inactive, but it is a useful stable frame for building %22smart%22 molecules and supramolecular assemblies. Suitable substitution on the upper (and/or lower) rim leads to unusual and surprising properties in this system. Polynitrocalix[4]arenes with reducible nitro groups located at the upper rim represent molecules with multiple redox centers where the potential for interactions between them is the focus of interest. The title compounds are promising precursors, e.g., for design and synthesis of sensors. In this work, the stepwise reduction of two tetranitrocalixarenes was investigated electrochemically, and the results were correlated with quantum chemical calculations. The order of individual electron transfers was described as a consequence of molecular geometry. Two independent pairs of equivalent nitro groups were identified whose reduction potential depends upon their respective locations in the molecule. All nitro groups are electronically isolated and thus are reduced independently yielding poly radical ions. The increasing charge has negligible impact on the geometry of the calixarene, which maintains its pinched shape even when carrying an overall molecular charge of 4. The calix[4]arene skeleton is electrochemically inactive, but it is a useful stable frame for building %22smart%22 molecules and supramolecular assemblies. Suitable substitution on the upper (and/or lower) rim leads to unusual and surprising properties in this system. Polynitrocalix[4]arenes with reducible nitro groups located at the upper rim represent molecules with multiple redox centers where the potential for interactions between them is the focus of interest. The title compounds are promising precursors, e.g., for design and synthesis of sensors. In this work, the stepwise reduction of two tetranitrocalixarenes was investigated electrochemically, and the results were correlated with quantum chemical calculations. The order of individual electron transfers was described as a consequence of molecular geometry. Two independent pairs of equivalent nitro groups were identified whose reduction potential depends upon their respective locations in the molecule. All nitro groups are electronically isolated and thus are reduced independently yielding poly radical ions. The increasing charge has negligible impact on the geometry of the calixarene, which maintains its pinched shape even when carrying an overall molecular charge of 4. (en)
Title	Electrochemical and Quantum Chemical Investigation of Tetranitrocalix[4]arenes: Molecules with Multiple Redox Centers Electrochemical and Quantum Chemical Investigation of Tetranitrocalix[4]arenes: Molecules with Multiple Redox Centers (en)
skos:prefLabel	Electrochemical and Quantum Chemical Investigation of Tetranitrocalix[4]arenes: Molecules with Multiple Redox Centers Electrochemical and Quantum Chemical Investigation of Tetranitrocalix[4]arenes: Molecules with Multiple Redox Centers (en)
skos:notation	RIV/00216208:11310/13:10172664!RIV14-MSM-11310___
http://linked.open...avai/predkladatel	Přírodovědecká fakulta
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GA13-21704S)
http://linked.open...iv/cisloPeriodika	21
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Vojtíšek, Pavel
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	72344
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/13:10172664
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	binding; calixarenes; 1,3-alternate conformation (en)
http://linked.open.../riv/klicoveSlovo	3-alternate conformation 1 calixarenes binding
http://linked.open...odStatuVydavatele	CH - Švýcarská konfederace
http://linked.open...ontrolniKodProRIV	[5494680F9584]
http://linked.open...i/riv/nazevZdroje	Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Electrochemically active calix[4]arenes and their use for preparation of new receptors and (bio)sensors
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	78
http://linked.open...iv/tvurceVysledku	Ludvík, Jiří Vojtíšek, Pavel Fry, Albert J. Liška, Alan
http://linked.open...ain/vavai/riv/wos	000326615300008
issn	0022-3263
number of pages	6 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jo4015613
http://localhost/t...ganizacniJednotka	11310

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