Elsevier

Dyes and Pigments

Volume 92, Issue 3, March 2012, Pages 1351-1354
Dyes and Pigments

Detection of singlet oxygen generated by commercial fine art organic pigments by means of a novel, robust chemical probe

https://doi.org/10.1016/j.dyepig.2011.09.018Get rights and content

Abstract

A novel, robust chemical method for the detection of singlet oxygen is reported. It uses the oxo-ene reaction of the largely available and inexpensive dicyclopentadiene which is transformed by singlet oxygen into a hydroperoxide, quantitatively converted in situ by acetic anhydride and pyridine into a stable ketone, easily detectable by standard GC. The method has been tested in the detection of singlet oxygen as generated by standard organic pigments used in commercially available tubes for fine art paintings.

Highlights

► We develop an original methodology for the detection of singlet oxygen. ► The methodology is based on oxo-ene reaction with inexpensive dicyclopentadiene. ► The method requires simple operations and equipment. ► The method was applied to test 15 modern organic pigments employed in fine arts. ► Pigments either inhibit the oxygen reactivity, or produced singlet oxygen.

Section snippets

Experimental

All reagents were used as purchased by suppliers without any further purification. Water colours were obtained from Maimeri S.p.A. Gas-chromatographic analysis were performed using a 15 m length, 025 mm i.d. column with 5% polydiphenysiloxane/95% polydimethylsiloxane 0.25 μm thick stationary phase, constant nitrogen flow 1.0 mL/min. Detector: FID. Linear correlation between product 4 and internal standard (n-tetradecane) was determined before analyses. Temperature ramp: 5 min at 50 °C followed

Acknowledgements

This work was co-founded by MIUR (Rome) within the national PRIN framework.

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    The intensely blue (in web version) HOCD has a very broad visible absorption spectrum ranging from 500 to 700 nm, which is readily bleached by 1O2 due to the formation of endoperoxide (Fig. 1) [7]. The long wavelength (>600 nm) is preferred for application because it will avoid background interference [8]. However, this property was only used in a limited report for detection of singlet oxygen.

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