Mechanism of photochemical reactions in solution. LXX. Photolysis of aryl esters

Meyer, James W.; Hammond, George S.

doi:10.1021/ja00762a010

Cited by 75 publications

(12 citation statements)

References 8 publications

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“…Recently, an amphiphilic PEG‐ block ‐poly((1‐pyrenyl methyl)methacrylate) copolymer was synthesized by atomic transfer radical polymerization. This polymer contains 1‐pyrenyl methylene units in the side chains that are readily cleaved from a poly(methacrylate) backbone via radical transition state . In water, the micelles were proven to be broken upon UV irradiation owing to the removal of the hydrophobic side groups and the resulting hydrophilic nature of the entire polymer .…”

Section: Introductionmentioning

confidence: 99%

“…This polymer contains 1-pyrenyl methylene units in the side chains that are readily cleaved from a poly(methacrylate) backbone via radical transition state. [27][28][29] In water, the micelles were proven to be broken upon UV irradiation owing to the removal of the hydrophobic side groups and the resulting hydrophilic nature of the entire polymer. 27 Different from the concept of generating potential light-sensitive "drug containers," we designed an amphiphilic PEG-block-poly((1-pyrenyl methyl) glutamate) (PEG-b-PGlu(Pyr)) copolymer that can stabilize particles in hydrophobic solvents and in water upon photolysis.…”

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confidence: 99%

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Polarity reversal of nanoparticle surfaces by the use of light‐sensitive polymeric emulsifiers

Dorresteijn

Billecke

Parekh

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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A polarity reversal of a nanoparticle surface with a light‐sensitive PEG‐block‐poly[(1‐pyrenyl methyl)glutamate] [(PEG‐b‐PGlu(Pyr)] copolymer is presented. The copolymer is successfully applied as an emulsifier in a nonaqueous emulsion polymerization of lactide. The hydrophobic pyrenyl methylene units are readily cleaved from the outer hydrophilic PGlu‐block by UV irradiation. The initially hydrophobic particles can then be dispersed in aqueous medium without the need of additional surfactants.

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Polarity reversal of nanoparticle surfaces by the use of light‐sensitive polymeric emulsifiers

Dorresteijn

Billecke

Parekh

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…inter alia ref. 4). The scope of the reaction has been greatly extended ( 5 ) and now encompasses amides (6-9).…”

Section: Introductionmentioning

confidence: 99%

Surface photochemistry: the amide Photo-Fries rearrangement

Abdel-Malik¹,

Mayo²

1984

Can. J. Chem.

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The Photo-Fries rearrangement of eight anilides on the surface of dry silica gel has been examined. The rearrangement occurs quite cleanly, giving somewhat more of the porn isomer than that obtained in methanolic solution. A test for intermolecularity on the silica gel surface showed that, as in solution, the radical pair intermediates do not separate. This contrasts with the behaviour of a previously reported dibenzyl ketone derivative.MAGDY M. ABDEL-MALIK et PAUL DE MAYO. Can. J. Chem. 62, 1275 (1984. On a ttudit la transposition de photo-Fries de huit anilides, i la surface de gei de silica scc. La transposition se produit d'une faqon assez propre; dans ce cas, il se forme plus d'isomtre porn qu'en solution mtthanolique. La dktermination de I'intermoltcularitt i la surface du gel de silica a dtmontrt que, comme en solution, la paire de radicaux intermtdiaires ne se stpare pas. Ceci est en opposition avec le comportement rapport6 antkrieurement pour un dtrivk de la dibenzylcktone.[Traduit par le journal]

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“…

Phenyl esters of aliphatic carboxylic acids show very low fluorescence quantum yields which frequently are below the sensitivity of the detection system employed (1 -3). This reduced fluorescence capacity, compared to that shown by other phenoxy compounds (2), is related to the fast rate of the competing photo-Fries-type bond cleavage (1,(3)(4)(5). The photochemical and photophysical behavior of poly(pheny1 acrylate) has been studied by Li and Guillet under different experimental conditions (6).

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confidence: 98%