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Description
| - A series of 10-arylflavins (10-phenyl- (2a), 10-(2,6-dimethylphenyl)- (2b), 10-(2,6-diethylphenyl)- (2c), 10-(2,6-diisopropylphenyl)- (2d), 10-(2-tert-butylphenyl)- (2e), and 10-(2,6-dimethylphenyl)-3-methyl- (2f) isoalloxazine) was prepared as potentially non-aggregating flavin photocatalysts. The investigation of their structures in the crystalline phase combined with 1H-DOSY NMR experiments in CD3CN, CD3CN/D2O 1:1 and in D2O confirm reduced ability of 10-arylflavins 2 to form aggregates in comparison with tetra-O-acetyl riboflavin (1). 10-Arylflavins 2a-2d do not interact by interactions, which are restricted by 10-phenyl ring oriented perpendicularly to the isoalloxazine skeleton. On the other hand, N(3)-H---O hydrogen bonds have been detected in their crystal structures. In the structure of 10-aryl-3-methylflavin (2f) with substituted N(3) position, weak C-H---O bonds and weak interactions have been found. 10-Arylflavins 2 were tested as photoredox catalysts for the aerial oxidation of 4-methoxybenzyl alcohol to the corresponding aldehyde (model reaction) showing higher efficiency compared to tetra-O-acetyl riboflavin (1). Quantum yields of 4-methoxybenzyl alcohol oxidations mediated by arylflavins 2 were higher by almost one order of magnitude compared to values in the presence of 1.
- A series of 10-arylflavins (10-phenyl- (2a), 10-(2,6-dimethylphenyl)- (2b), 10-(2,6-diethylphenyl)- (2c), 10-(2,6-diisopropylphenyl)- (2d), 10-(2-tert-butylphenyl)- (2e), and 10-(2,6-dimethylphenyl)-3-methyl- (2f) isoalloxazine) was prepared as potentially non-aggregating flavin photocatalysts. The investigation of their structures in the crystalline phase combined with 1H-DOSY NMR experiments in CD3CN, CD3CN/D2O 1:1 and in D2O confirm reduced ability of 10-arylflavins 2 to form aggregates in comparison with tetra-O-acetyl riboflavin (1). 10-Arylflavins 2a-2d do not interact by interactions, which are restricted by 10-phenyl ring oriented perpendicularly to the isoalloxazine skeleton. On the other hand, N(3)-H---O hydrogen bonds have been detected in their crystal structures. In the structure of 10-aryl-3-methylflavin (2f) with substituted N(3) position, weak C-H---O bonds and weak interactions have been found. 10-Arylflavins 2 were tested as photoredox catalysts for the aerial oxidation of 4-methoxybenzyl alcohol to the corresponding aldehyde (model reaction) showing higher efficiency compared to tetra-O-acetyl riboflavin (1). Quantum yields of 4-methoxybenzyl alcohol oxidations mediated by arylflavins 2 were higher by almost one order of magnitude compared to values in the presence of 1. (en)
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Title
| - Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins
- Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins (en)
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skos:prefLabel
| - Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins
- Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins (en)
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skos:notation
| - RIV/60461373:22310/13:43895601!RIV14-MSM-22310___
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http://linked.open...avai/predkladatel
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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/60461373:22310/13:43895601
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - photocatalysis; oxidation; organocatalysis; noncovalent interactions; flavins; aggregation (en)
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http://linked.open.../riv/klicoveSlovo
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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
| - Chemistry A European Journal
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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
| - Cibulka, Radek
- Maixner, Jaroslav
- Cibulková, Jana
- Pažout, Richard
- Daďová, Jitka
- König, Burkhard
- Feldmeier, Christian
- Gschwind, Ruth
- Kümmel, Susanne
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http://linked.open...ain/vavai/riv/wos
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issn
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number of pages
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http://bibframe.org/vocab/doi
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http://localhost/t...ganizacniJednotka
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