Abstract
meso-Aryl-substituted (biscyclohexano)bis(ethoxycarbonyl)BODIPY [aryl = phenyl, 3,4-dimethoxyphenyl, and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl-(m-{benzo-15-crown-5}-yl)] were synthesized. The effect of alkaline-earth metals on the absorption and fluorescence spectra of these compounds was investigated. In all compounds along with the mechanism of the photoinduced electron transfer (PET), well-known for the crown-containing BODIPY-based sensors, one more response pattern is observed. The large excess of Ca2+ and Ba2+ ions in the system leads to the changes both in the UV-Vis and emission spectra. The complex formation results in the decrease of emission intensity and in its red shift. Besides, a new longwave absorption band appears in the UV-Vis spectrum of the BODIPY-metal ion complex. The formation constants of the complexes corresponding to this response pattern is about 100 times less than the formation constant of Ca2+-crown ether complex. 1H, 13C, 11B, and 19F NMR spectra, the results of quantum-chemical calculations, and their comparison with the literature data of X-ray diffraction study suggest that the binding of Ca2+ and Ba2+ ions occurs in the cavity formed by the fluorine atoms and the carbonyl oxygen atoms of the ester groups.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
