I have discovered that the asimmetric bodipy (actually the raw mixture after solvent removal and before the chormatography) is stable for weeks at room T and air. Another point is that I tried to extract al the amine from the mixture with DCM/water+HCl . Then to the final product I added some amount of silica gel to simulate the chromatography and the next day I found no decomposition. Of course Amine catalyze hydrolisis and binding to silica matrix, but this do not explain the decomposition of the bodipy moiety and most of all the different behaviour of simmetric and asymmetric bodipy (the former is uneffected and is stable even after the chirmatography without work up after the reaction).
So to summarize
- both symmetric and asymmetric bodipy are stable before chormatography (in the raw dry mixture with amines and other compunds that formes during the reaction)
-purification though silica gel starts asymmetric bodipy decomposition , but leaves the symmetric one uneffected
-working up the reaction seems to make the asymmetric boidipy stable after purification through silica gel (but I tried only one time and in small scale)