초록 |
Bisacetoacetamides 1 and 2 having two 1,3-diketo groups were prepared by the reaction of aromatic amines with diketene. Diazonium salts 3 and 4 were prepared by the reaction of aromatic amines with nitrous HCl and followed by treatment with sodium fluoroborate to isolate in a stable diazonium fluoroborate. The hydrazone polymers were prepared by the diazo coupling reaction of bisacetoacetamides with diazonium salts under mild basic conditions. In the 1H NMR and FT-IR spectroscopy, we identified that the polymers exist in hydrazone form in a solid and solution state, and the hydrazone unit is stabilized by the intramolecular hydrogen bonding. It was also observed that UV/Vis. maximum absorptions of polymers 7 and 8 were changed from 378 to 450 nm, from 384 to 448 nm, respectively, after the addition of a small amount of piperidine. Therefore, hydrazone polymers 7 and 8 exist in hydrazone-common anion equilibria in a basic solution. |