REAGENTS FOR DIRECTED MODIFICATION OF BIOPOLYMERS - 9 - DERIVATIVES OF 6-AZIDOHEXAFLUORO-2-NAPHTHOIC ACID - SYNTHESIS AND PHOTOCHEMICAL PROPERTIES

The synthesis of new heterobifunctional reagents that are photo-activa ted, namely, 6-azido-1,3,4,5,7,8-hexafluoro-2-naphthoic acid (2), nimi do-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 az ides 2 and 4 in methanol and pyridine was studied. Azide 4 is superior to photoreagents based on perfluoroaromatic azides of the benzene ser ies in spectral photosensitivity and rate of photolysis in the UV regi on (334-405 nm). When azide 4 is irradiated with light at wavelengths above 400 nm, the rate of its photolysis in methanol increases cn. 10- fold in the presence of a singlet sensitizer, 9-aminoacridine, which m akes reagent 3 promising for designing binary systems sensitive to vis ible light.