Polymer-based sensitizers for photooxidations

Blossey, Erich C.; Neckers, Douglas C.; Thayer, Arthur L.; Schaap, A. Paul

doi:10.1021/ja00798a094

Cited by 160 publications

(60 citation statements)

References 1 publication

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“…-IH-NMR. (CD3COCD3): 2.94 (d, 2J=5.2, 1 H, one of H>C-C(2)); 2.84 (d, 2J=4.6, 1 H, the other of HzC-C(2)); 2.75 (d, 2J=5.2, 1 H, one of H2C-C(3)); 2.63 (d, 2J=4.6, 1 H, the other of H2C-C(3)), 2.4-1.3 (m, 8 H, H-C(l), H-C(4), H2C(5), HzC (6) and HzC (7)). -I3C-NMR.…”

Section: Synthesis Ofmentioning

confidence: 99%

Effects of Remote Substitution on the Photo‐oxidation of Exocyclic s‐cis‐Butadienes Grafted onto Bicyclo [2.2.1]heptanes. Thermal and Rhodium Catalyzed Rearrangements of 3,6‐Dihydro‐1,2‐dioxines

Hagenbuch

Birbaum

Métral

et al. 1982

Helvetica Chimica Acta

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SummaryThe rates of photo-oxidation of exocyclic s-cis-butadienes grafted onto bicyclo-[2.2. llheptanes and 7-oxabicyclo[2.2. llheptanes (1-6) are dependent upon remote modifications of the bicyclic skeletons. They correlate with the rates of Diels-Alder additions of these dienes to strong dienophiles. The 2,3-dimethylidenenorbornane (l), 5,6-dimethylidene-2-norbornene (2) and 2,3-dimethylidene-7-oxanorbornane (3) gave the corresponding endo-peroxides (3,6-dihydro-1,2-dioxines) 7-9 in good yield. The 2,3,5,6-tetramethylidene-7-oxanorbornane (4) gave the mono-endo-peroxide 6, the latter did not react with a second equivalent of oxygen. Similarly, 5,6-dimethylidene-7-oxa-2-norbornene (5) was unreactive toward photo-oxidation. Thermal isomerization of the endo-peroxides 7 and 9 gave the trans-diepoxides 10 and 14, respectively, with high stereoselectivity. The endo-peroxides 6 , 7 and 9 were cleanly isomerized into the corresponding a. /?-unsaturated y-hydroxy aldehydes in the presence of catalytic amounts of Rh, (CO)&l2.

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Section: Synthesis Ofmentioning

confidence: 99%

Effects of Remote Substitution on the Photo‐oxidation of Exocyclic s‐cis‐Butadienes Grafted onto Bicyclo [2.2.1]heptanes. Thermal and Rhodium Catalyzed Rearrangements of 3,6‐Dihydro‐1,2‐dioxines

Hagenbuch

Birbaum

Métral

et al. 1982

Helvetica Chimica Acta

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“…[13][14][15][16][17][18][19][20] This last polymer is one of the most popular supports employed so far, dating back to the pioneering works of Schaap and Neckers. 36 Polystyrene is a versatile system, used in applications as diverse as fluorescence sensing 37 or catalysis. 38 In catalysis, this polymer is the basic scaffold of many ion exchange resins 39 and as a matter of fact some of those resins were employed very early to support ionic photosensitizers for the generation of singlet oxygen.…”

Section: Introductionmentioning

confidence: 99%

Superior performance of macroporous over gel type polystyrene as a support for the development of photo-bactericidal materials

et al. 2017

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a Hexanuclear molybdenum cluster [Mo6I8Ac6] 2-(1) has been ionically bound onto macroporous (Pmp) and gel-type (Pgel) resins and their performance as materials for the photodynamic inactivation of microorganism have been studied. It has been found that 1@Pmp in combination with light is able to reduce 99.999999% the population of Gram-positive Staphylococcus aureus whereas the activity of 1@Pgel is limited to a 99.99% reduction at the same light dose. The same trend is observed with Gram-negative Pseudomonas aeruginosa. A comprehensive study of both materials has been performed using confocal laser scanning microscopy, thermogravimetric analysis, nitrogen porosimetry, steady state and time resolved fluorometries and diffuse reflectance spectroscopy. The photochemical generation of singlet oxygen ( 1 O2) has been assessed using 9,10-dimethylanthracene as a trap for this reactive oxygen species. It can be concluded that the nature of the polymeric support is of paramount importance for the development of surfaces with bactericidal properties.

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“…Problems with solvent incompatibilities of sensitizer and 10 2 acceptor can be overcome (Buell & Demas, 1983). Some well known examples are RB chemically bound to silica gel (Blossey et al, 1973 ;Tamagaki et al, 1980) or the commercially available RB-polymer complexes (Schaap et al, 1979), and resin-bound tris(2,2'-bipyridine)ruthenium(II) (Buell & Demas, 1983).…”

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confidence: 99%

Tryptophan Photo-Oxidation by Clay-Adsorbed Sensitizers

Cenens

Schoonheydt

1988

Clay miner.

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A B S T R A C T :The photo-oxidation of tryptophan (TRP), photosensitized by methylene blue (MB) exchanged on hectorite, Wyoming bentonite and laponite is strongly influenced by three factors: (i) Fe(III) in the structure, which quenches the excited state of MB; (ii) the adsorption site of MB, as photo-oxidation only takes place with MB on the external surface; (iii) dye aggregation, which reduces the yield. Rose bengal (RB), chemically anchored on the external surface of Barasym does not sensitize the photo-oxidation of TRP.Two electronically excited singlet states of oxygen are located 94.3 and 157

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Polymer-based sensitizers for photooxidations

Cited by 160 publications

References 1 publication

Effects of Remote Substitution on the Photo‐oxidation of Exocyclic s‐cis‐Butadienes Grafted onto Bicyclo [2.2.1]heptanes. Thermal and Rhodium Catalyzed Rearrangements of 3,6‐Dihydro‐1,2‐dioxines

Effects of Remote Substitution on the Photo‐oxidation of Exocyclic s‐cis‐Butadienes Grafted onto Bicyclo [2.2.1]heptanes. Thermal and Rhodium Catalyzed Rearrangements of 3,6‐Dihydro‐1,2‐dioxines

Superior performance of macroporous over gel type polystyrene as a support for the development of photo-bactericidal materials

Tryptophan Photo-Oxidation by Clay-Adsorbed Sensitizers

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