About: Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins     Goto   Sponge   NotDistinct   Permalink

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  • 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)
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)
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)
skos:notation
  • RIV/60461373:22310/13:43895601!RIV14-MSM-22310___
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  • S
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  • 3
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  • 59744
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  • RIV/60461373:22310/13:43895601
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  • photocatalysis; oxidation; organocatalysis; noncovalent interactions; flavins; aggregation (en)
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  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [F749792B80B4]
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  • Chemistry A European Journal
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  • 19
http://linked.open...iv/tvurceVysledku
  • Cibulka, Radek
  • Maixner, Jaroslav
  • Cibulková, Jana
  • Pažout, Richard
  • Daďová, Jitka
  • König, Burkhard
  • Feldmeier, Christian
  • Gschwind, Ruth
  • Kümmel, Susanne
http://linked.open...ain/vavai/riv/wos
  • 000313263300033
issn
  • 0947-6539
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/chem.201202488
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  • 22310
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