Photo-substitution reactions of perylene red dyes

Johan Lub (Corresponding author), Paul A. van Hal, Erica M.G. Custers, Hugo H. Knobel, Rifat A.M. Hikmet

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Irradiation of Lumogen Red 305 (3) in ethyl acetate with intense blue LED light led to very slow bleaching, showing a high photochemical stability. However, irradiation in ethanol led to the formation of a low yield product in which one of the phenoxy groups is substituted by an acetoxy group, the oxidized form of an ethoxy group. This reaction product was only formed in the presence of blue light and oxygen. Adding a small amount of acetic acid to the solutions resulted in a much higher yield of the product, indicating a possible photo oxidation of ethanol to acetic acid during the process in this solvent. A similar dye (5) containing less phenoxy side groups than Lumogen Red 305 showed the same reaction although the product formed showed lower chemical stability. The photo-substitution of phenoxy groups by acetoxy groups is a new reaction. The results are used to discuss the structural effects on the stability of these type of fluorescent dyes under irradiation conditions, potential reaction mechanisms and the possibility of using the photochemical transformations for preparative purposes.

LanguageEnglish
Article number116845
JournalJournal of Luminescence
Volume218
DOIs
StatePublished - 1 Feb 2020

Fingerprint

Perylene
Acetic Acid
Substitution reactions
Ethanol
Coloring Agents
dyes
Irradiation
substitutes
Light
Fluorescent Dyes
Photooxidation
Chemical stability
Oxygen
Bleaching
Reaction products
acetic acid
irradiation
Light emitting diodes
ethyl alcohol
products

Keywords

  • Fluorescent compounds
  • Lumogen red 305
  • Photo stability
  • Photo substitution
  • Photo-oxidation

Cite this

Lub, J., van Hal, P. A., Custers, E. M. G., Knobel, H. H., & Hikmet, R. A. M. (2020). Photo-substitution reactions of perylene red dyes. Journal of Luminescence, 218, [116845]. DOI: 10.1016/j.jlumin.2019.116845
Lub, Johan ; van Hal, Paul A. ; Custers, Erica M.G. ; Knobel, Hugo H. ; Hikmet, Rifat A.M./ Photo-substitution reactions of perylene red dyes. In: Journal of Luminescence. 2020 ; Vol. 218.
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Lub, J, van Hal, PA, Custers, EMG, Knobel, HH & Hikmet, RAM 2020, 'Photo-substitution reactions of perylene red dyes' Journal of Luminescence, vol. 218, 116845. DOI: 10.1016/j.jlumin.2019.116845

Photo-substitution reactions of perylene red dyes. / Lub, Johan (Corresponding author); van Hal, Paul A.; Custers, Erica M.G.; Knobel, Hugo H.; Hikmet, Rifat A.M.

In: Journal of Luminescence, Vol. 218, 116845, 01.02.2020.

Research output: Contribution to journalArticleAcademicpeer-review

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AU - Lub,Johan

AU - van Hal,Paul A.

AU - Custers,Erica M.G.

AU - Knobel,Hugo H.

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N2 - Irradiation of Lumogen Red 305 (3) in ethyl acetate with intense blue LED light led to very slow bleaching, showing a high photochemical stability. However, irradiation in ethanol led to the formation of a low yield product in which one of the phenoxy groups is substituted by an acetoxy group, the oxidized form of an ethoxy group. This reaction product was only formed in the presence of blue light and oxygen. Adding a small amount of acetic acid to the solutions resulted in a much higher yield of the product, indicating a possible photo oxidation of ethanol to acetic acid during the process in this solvent. A similar dye (5) containing less phenoxy side groups than Lumogen Red 305 showed the same reaction although the product formed showed lower chemical stability. The photo-substitution of phenoxy groups by acetoxy groups is a new reaction. The results are used to discuss the structural effects on the stability of these type of fluorescent dyes under irradiation conditions, potential reaction mechanisms and the possibility of using the photochemical transformations for preparative purposes.

AB - Irradiation of Lumogen Red 305 (3) in ethyl acetate with intense blue LED light led to very slow bleaching, showing a high photochemical stability. However, irradiation in ethanol led to the formation of a low yield product in which one of the phenoxy groups is substituted by an acetoxy group, the oxidized form of an ethoxy group. This reaction product was only formed in the presence of blue light and oxygen. Adding a small amount of acetic acid to the solutions resulted in a much higher yield of the product, indicating a possible photo oxidation of ethanol to acetic acid during the process in this solvent. A similar dye (5) containing less phenoxy side groups than Lumogen Red 305 showed the same reaction although the product formed showed lower chemical stability. The photo-substitution of phenoxy groups by acetoxy groups is a new reaction. The results are used to discuss the structural effects on the stability of these type of fluorescent dyes under irradiation conditions, potential reaction mechanisms and the possibility of using the photochemical transformations for preparative purposes.

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Lub J, van Hal PA, Custers EMG, Knobel HH, Hikmet RAM. Photo-substitution reactions of perylene red dyes. Journal of Luminescence. 2020 Feb 1;218. 116845. Available from, DOI: 10.1016/j.jlumin.2019.116845