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| Description
| - Stable, highly colored push-pull chromophores with NMe2 donor and C=C(CN)2 acceptor moieties, featuring intense intramolecular charge-transfer (CT) bands in the UV/Vis spectra, are reported. In an attempt to prepare the quinoid pushpull systems 2, chromophores 10 and 11, with a central cyclohexene spacer, were obtained and characterized by X-ray analysis. A series of donor-substituted TCAQ (11,11,12,12- tetracyano-9,10-anthraquinodimethane) derivatives were synthesized, using the Knoevenagel condensation between appropriately functionalized anthraquinones and malononitrile, mediated by the Lehnert reagent (TiCl4/pyridine), as the key step. HCl addition to triple bonds was observed when this transformation was applied to alkynylated anthraquinones. Electrochemical studies by cyclic voltammetry (CV) and rotating-disk voltammetry (RDV) showed that introduction of donor substituents into the TCAQ core of 25, 26, and 31 shifts the first reduction potential to more negative values, while chromophores bear
- Stable, highly colored push-pull chromophores with NMe2 donor and C=C(CN)2 acceptor moieties, featuring intense intramolecular charge-transfer (CT) bands in the UV/Vis spectra, are reported. In an attempt to prepare the quinoid pushpull systems 2, chromophores 10 and 11, with a central cyclohexene spacer, were obtained and characterized by X-ray analysis. A series of donor-substituted TCAQ (11,11,12,12- tetracyano-9,10-anthraquinodimethane) derivatives were synthesized, using the Knoevenagel condensation between appropriately functionalized anthraquinones and malononitrile, mediated by the Lehnert reagent (TiCl4/pyridine), as the key step. HCl addition to triple bonds was observed when this transformation was applied to alkynylated anthraquinones. Electrochemical studies by cyclic voltammetry (CV) and rotating-disk voltammetry (RDV) showed that introduction of donor substituents into the TCAQ core of 25, 26, and 31 shifts the first reduction potential to more negative values, while chromophores bear (en)
- V této práci jsou publikovány stabilní, barevné push-pull chromofory s NMe2 donory a C=C(CN)2 akceptory vykazující intenzivní CT pásy v UV/Vis spektrech. Při pokusech připravit chinoidní systémy typu 2 byly izolovány, a pomocí X-ray analýzy charakterizovány, chromofory 10 a 11 obsahující centrální cyklohexenové jádro. Za použití Knoevenagelovy kondenzace malononitrilu a vhodně substituovaných anthra-9,10-chinonů, katalyzované Lehnertovým činidlem (TiCl4/pyridin), byla syntetizována série donor substituovaných TCAQ. Byla pozorována adice HCl na trojnou vazbu pokud byl jako výchozí anthrachinon využit alkynylovaný derivát. Elektrochemické studie ukázaly (CV, RDV), že zavedení donorních substituentů na TCAQ jádro sloučenin 25, 26 a 31 posouvá první redukční potenciál k negativním hodnotám zatímco chromofory obsahující guanidinový zbytek vykazují specifické redox chování. Elektrochemické jakožto UV/Vis data poskytují dobré důkazy o efektivnější D-A konjugaci přes olefinický než přes acetylenový můstek. (cs)
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| Title
| - New Push-Pull Chromophores Featuring TCAQ (11,11,12,12-Tetracyano-9,10-anthraquinodimethane) and Other Dicyanovinyl Acceptors
- New Push-Pull Chromophores Featuring TCAQ (11,11,12,12-Tetracyano-9,10-anthraquinodimethane) and Other Dicyanovinyl Acceptors (en)
- Nové push-pull chromofory obsahující TCAQ (11,11,12,12-Tetrakyano-9,10-anthrachinodimethan) a jiné dikyanovinyl akceptory (cs)
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| skos:prefLabel
| - New Push-Pull Chromophores Featuring TCAQ (11,11,12,12-Tetracyano-9,10-anthraquinodimethane) and Other Dicyanovinyl Acceptors
- New Push-Pull Chromophores Featuring TCAQ (11,11,12,12-Tetracyano-9,10-anthraquinodimethane) and Other Dicyanovinyl Acceptors (en)
- Nové push-pull chromofory obsahující TCAQ (11,11,12,12-Tetrakyano-9,10-anthrachinodimethan) a jiné dikyanovinyl akceptory (cs)
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| skos:notation
| - RIV/00216275:25310/08:00006168!RIV09-MSM-25310___
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| http://linked.open...avai/riv/aktivita
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| http://linked.open...avai/riv/aktivity
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| http://linked.open...iv/cisloPeriodika
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| http://linked.open...vai/riv/dodaniDat
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| http://linked.open...aciTvurceVysledku
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| http://linked.open.../riv/druhVysledku
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| http://linked.open...iv/duvernostUdaju
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| http://linked.open...titaPredkladatele
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| http://linked.open...dnocenehoVysledku
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| http://linked.open...ai/riv/idVysledku
| - RIV/00216275:25310/08:00006168
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| http://linked.open...riv/jazykVysledku
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| http://linked.open.../riv/klicovaSlova
| - Donor?acceptor chromophores / 11; 11; 12; 12-Tetracyano-9; 10-anthraquinodimethane (TCAQ) / Charge transfer/ Electrochemistry / Pi conjugation / Quinodimethanes (en)
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| http://linked.open.../riv/klicoveSlovo
| |
| http://linked.open...odStatuVydavatele
| - DE - Spolková republika Německo
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| http://linked.open...ontrolniKodProRIV
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| http://linked.open...i/riv/nazevZdroje
| - European Journal of Organic Chemistry
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| http://linked.open...in/vavai/riv/obor
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| http://linked.open...ichTvurcuVysledku
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| http://linked.open...cetTvurcuVysledku
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| http://linked.open...UplatneniVysledku
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| http://linked.open...v/svazekPeriodika
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| http://linked.open...iv/tvurceVysledku
| - Bureš, Filip
- Diederich, Francois
- Gisselbrecht, Jean-Paul
- Schweizer, Bernd W.
- Boudon, Corinne
- Gross, Maurice
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| http://linked.open...n/vavai/riv/zamer
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| issn
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| number of pages
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| http://localhost/t...ganizacniJednotka
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