Reagents for directed modification of biopolymers 9. Derivatives of 6-azidohexafluoro-2-naphthoic acid. Synthesis and photochemical properties

Article abstract of DOI:10.1007/BF02498959

The synthesis of new heterobifunctional reagents that are photo-activated, namely, 6-azido-1,3,4,5,7,8-hexafluoro-2-naphthoic acid (2), succinimido-6-azido-1,3,4,5,7,8-hexafluoro-2-naphthoate (3), and N-(n-butyl)-1,3,4,5,7,8-hexafluoro-2-naphthamide (4), which simulates the product of addition of acid 2 to biopolymers, is described. The photolysis of azides 2 and 4 in methanol and pyridine was studied. Azide 4 is superior to photoreagents based on perfluoroaromatic azides of the benzene series in spectral photosensitivity and rate of photolysis in the UV region (334-405 nm). When azide 4 is irradiated with light at wavelengths above 400 nm, the rate of its photolysis in methanol increases ca. 10-fold in the presence of a singlet sensitizer, 9-aminoacridine, which makes reagent 3 promising for designing binary systems sensitive to visible light.