Green photochemistry: solar photooxygenations with medium concentrated sunlight

Oelgemöller, Michael; Jung, Christian; Ortner, J.; Mattay, Jochen; Zimmermann, Elmar

doi:10.1039/b414230f

Cited by 82 publications

(62 citation statements)

References 32 publications

(1 reference statement)

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“…The solution was concentrated to 30 mL, 1 mL of pyridine was added followed by 300 mg of the aminoalkylated polymers AAP1 (AAP2, AAP3 or PSDV-NH 2 ). The mixture was stirred overnight at 30 C, filtered, and washed with dichloromethane, tetrahydrofuran, methanol, and dichloromethane again. Non-bonding porphyrin was eliminated with these washings.…”

Section: Synthesis Of Polymeric Photosensitizers Ps1 To Ps4mentioning

confidence: 99%

Covalently immobilized porphyrins as photooxidation catalysts

2007

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Section: Synthesis Of Polymeric Photosensitizers Ps1 To Ps4mentioning

confidence: 99%

Covalently immobilized porphyrins as photooxidation catalysts

2007

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“…[1,2] In this connection, microstructured reactors (MRs) [3] represent an interesting alternative to conventional photoreactors because the small size of the fluidic channels leads to higher spatial illumination homogeneity and better light penetration through the entire reactor depth. Also, the elevated surfaceto-volume ratio features of MRs allow an effective reagent mixing, enhanced heat-and mass-transfer rates and safer processing of toxic or highly reactive compounds.…”

Section: Introductionmentioning

confidence: 99%

Fullerene‐Promoted Singlet‐Oxygen Photochemical Oxygenations in Glass‐Polymer Microstructured Reactors

et al. 2008

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In this paper we report the fabrication of thiolene-based microstructured reactors (MRs) that have been specifically designed to include solid-supported reagents within the microchannels network. We propose a convenient solution to realize reversible press-fit, leak-proof interconnects that greatly simplify the MR coupling to the external environment such as capillary tubing, sample reservoirs and pumps. The MRs have been used to carry out the oxidation of alpha-terpinene and methionine using [60]fullerene, covalently linked to Tentage](R) and silica gel matrices, as a singlet oxygen sensitizer. High conversions have been observed for both substrates although, in the case of a-terpinene, a partial photodegradation of the endo-peroxide product was detected. Interestingly, in the case of methionine, a quantitative conversion to the corresponding sulfoxides was achieved in about 40 seconds, using lowpower, white LED illumination. The reaction time is considerably shorter when compared to the batch procedure that requires, for the same process, about one hour illumination and the use of a 300-W tungsten halogen lam

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“…No photoacylation reaction was detected when water, EtOH; MeOH; 1-ButOH;1-PrOH and DMK were employed as the solvent media. It is worth to note that precedents on the photoacylation of naphthoquinone 1 with butyraldehyde in t-BuOH and in 3:1 t-ButOH/DMK mixture, employing artificial 11,12 and solar light, 13 gave the respective acylhydroquinone in 84 and 90% yield, respectively. In the light of these precedents and taking into account the above results on the influence of the solvent media on the photoacylation to produce acylated hydroquinone 2, we wanted to examine the effect of binary and ternary green solvent mixtures on the photoacylation of quinone 1 with furfural.…”

Section: Experimental Generalmentioning

confidence: 99%

Green Synthetic Approaches to Furoylnaphthohydroquinone and Juglone

Benites

Michael

Luis

et al. 2014

J. Chil. Chem. Soc.

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The synthesis of two valuable precursors of biological active compounds named 2-(furan-2-yl)-1,4-dihydroxynapthohydroquinone 2 and 5-hydroxy-1,4-naphthoquinone (4, juglone) via solar photo-induced reactions from 1,4-naphthoquinone 1 and 1,5-dihydroxynaphthalene 3 in green solvent media is reported. When t-butyl alcohol and the binary t-ButOH/DMK and ternary i-PrOAc/DMK/MEK solvent mixtures were used, acylhydroquinone 2 was isolated in yields of 80, 83 and 77%, respectively. The sensitized photooxygenation of 3 "on water" and in water containing sodium dodecyl sulfate produce juglone 4 in 81 and 39% yields respectively.

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Green photochemistry: solar photooxygenations with medium concentrated sunlight

Cited by 82 publications

References 32 publications

Covalently immobilized porphyrins as photooxidation catalysts

Covalently immobilized porphyrins as photooxidation catalysts

Fullerene‐Promoted Singlet‐Oxygen Photochemical Oxygenations in Glass‐Polymer Microstructured Reactors

Green Synthetic Approaches to Furoylnaphthohydroquinone and Juglone

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