Photochemistry of Nitro and Nitroso Compounds

Carboxylic acids conjugated with 4,5-dimethoxy-2-nitrobenzyl photoremovable protecting group are well known and widely used for biological studies. In this paper, we study the photolysis of likewise “caged” acetic, caprylic and arachidonic acids. Unexpectedly, we observed huge growth of fluorescence emission at ~430 nm during photolysis. Following further UV irradiation, a product with fluorescence at longer wavelength was formed (470 nm excitation / ~500–600 nm emission). While it may be used to monitor the “uncaging”, these fluorescent products may interfere with widespread dyes such as fluorescein in biomedical experiments. This effect might be negligible if the photolysis products dissolve in the medium. On the other hand, we observed that arachidonic and caprylic acids derivatives self-organize in emulsion droplets in water environment due to long lipophilic chains. Illumination of droplets by UV rapidly induces orange fluorescence excited by 488 nm light. This fluorescence turn-on was fast (~0.1 s) and apparently caused by the accumulation of water-insoluble fluorescent residuals inside droplets. These self-organized lipophilic structures with fluorescence turn-on capability may be of interest for biomedical and other application. We have identified and hypothesized some compounds which may be responsible for the observed fluorescense.

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o-Nitrophenylethylene glycol as photoremovable protective group for aldehydes and ketones: syntheses, scope, and limitations

Gravel¹,

Hébert²,

Thoraval³

1983

Can. J. Chem.

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The preparation of o-nitrophenylethylene glycol is described along with its application as a photolabile protective group for aldehydes and ketones. Formation of the acetals and ketals is achieved in good to high yields in the usual manner and deprotection is carried out in fair to high yield, by photolysis at 350 nm in an inert solvent such as benzene. Because of the particular nature of the present protective group, its stability to basic and acidic conditions has been examined and is reported to complete the scope and limitations aspect. From a mechanistic point of view, the isolation and characterization of o-nitroso-α-hydroxyacetophenone as the spent reagent demonstrates a mechanistic link with the known o-nitrobenzaldehyde to o-nitrosobenzoic acid photorearrangement.

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Photochemistry of Nitro and Nitroso Compounds

Abstract: Introduction Photochemistry of Aromatic Nitro Compounds Photochemistry of Nitro‐Olefins Photochemistry of Aliphatic Nitro Compounds Photochemistry of C ‐Nitroso Compounds Photochemistry of Alkyl Nitrites Photochemistry of … Show more

Cited by 7 publications

References 187 publications

First, serendipitous and intriguing hydrolysis of a tertiary nitroalkane

First, serendipitous and intriguing hydrolysis of a tertiary nitroalkane

Photolysis of dimethoxynitrobenzyl-“caged” acids yields fluorescent products

o-Nitrophenylethylene glycol as photoremovable protective group for aldehydes and ketones: syntheses, scope, and limitations

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