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Synthesis and photochemical reaction of benzo[ a ]quinoxalino[2,3‐ c ]phenazine dyes
Author(s) -
Podsiadły Radosław,
Sokołowska Jolanta,
Kolińska Jolanta,
Grzelakowska Aleksandra
Publication year - 2017
Publication title -
coloration technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.297
H-Index - 49
eISSN - 1478-4408
pISSN - 1472-3581
DOI - 10.1111/cote.12300
Subject(s) - phenazine , chemistry , photochemistry , photodissociation , fluorescence , quantum yield , absorption spectroscopy , mass spectrometry , absorption (acoustics) , irradiation , organic chemistry , materials science , physics , chromatography , quantum mechanics , composite material , nuclear physics
Novel dyes based on the benzo[ a ]quinoxalino[2,3‐ c ]phenazine skeleton and necessary intermediates (benzo[ a ]phenazine‐5,6‐diones) were synthesized. The heterocyclic dyes and benzo[ a ]phenazine‐5,6‐diones were characterized using 1 H nuclear magnetic resonance ( NMR ) spectroscopy and chemical ion ( CI ) mass spectrometry. Their spectral properties, such as absorption and emission spectra and fluorescence quantum yield, were also measured. Experimental results demonstrated that photolysis of benzo[ a ]quinoxalino[2,3‐ c ]phenazine dyes in 2‐propanol and cyclohexene oxide leads to dihydro derivatives. The same product is formed during irradiation of dye/iodonium salt photoredox pairs in monomers. These compounds absorb incident light at longer wavelength and act as in situ sensitizers. Thus, when a composition was irradiated with a xenon lamp through a 395 cutoff filter, higher conversion was achieved than under monochromatic light.