Research On The Synthesis And Spectrum Property Of Aza-BODIPY Fluorescence Compounds

Aza-BODIPY(Aza-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)is a new fluorescence compound which developed and was paid close attention to in resent years.Its derivatives have distinct fluorescence characteristics:longer absorption and emission wavelength,higher fluorescent quantum yield,higher molar absorption absorptivity,sharp half peak width and high photostability,etc.Furthermore,Aza-BODIPY dyes are amenable to modifications,which allow fine-tuning of properties by introduction of suitable substituents at appropriate positions of the dipyrrin framework.The main work of the paper include the following two parts:1.In this study,Aza-BODIPY derivatives were synthesised from aromatic ketones and aromatic aldehydes via four-step reactions.At frist,a series of chalcone analogues 1 were synthesized from the reaction of Aldol-condensation.Then intermediates 2 was synthesized through Michael addition reaction using chalcone and nitromethane.Azadipyrromethene chromophore group 3 were obtained with intermediates 2 and ammonium acetate.Finally,the target compounds 4 were obtained from the reaction of 3 with Boron trifluoride diethyl ether(BF3·Et20).The affecting factors of each steps and the sythetic conditions were discussed and optimized in the paper.Ultimately,we got 31 Aza-BODIPY compounds in all,including 24 new compounds.The structures of all the 31 compounds were characterized by 1H NMR spectra.2.The ultraviolet-visible absorption spectrum and fluorescence spectrum of all the 31 compounds were measured.Then fluorescent quantum yield were calculated.All the compounds have a larger molar absorptivity in the long wavelength region(greater than 650nm),maximum 1.4×105L·mol-1·cm-1.Most of the compounds have good performance in fluorescent quantum yield,up to 0.73.On this basis,the relation between the photophysical properties and the structure of the dyes were investigated.