. "Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins"@en . "Chemistry A European Journal" . . . "S" . . "Pa\u017Eout, Richard" . "Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins" . "Gschwind, Ruth" . "K\u00F6nig, Burkhard" . . "Da\u010Fov\u00E1, Jitka" . . "Feldmeier, Christian" . . . . "photocatalysis; oxidation; organocatalysis; noncovalent interactions; flavins; aggregation"@en . . . . "K\u00FCmmel, Susanne" . "3" . "Maixner, Jaroslav" . "RIV/60461373:22310/13:43895601!RIV14-MSM-22310___" . "10"^^ . "22310" . "Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins"@en . "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 . "9"^^ . . "19" . "[F749792B80B4]" . "DE - Spolkov\u00E1 republika N\u011Bmecko" . . "59744" . "0947-6539" . . . "Cibulka, Radek" . "000313263300033" . "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." . "Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins" . "2"^^ . . . "RIV/60461373:22310/13:43895601" . "10.1002/chem.201202488" . . "Cibulkov\u00E1, Jana" .