An efficient Al3+ receptor, 6-(2-hydroxybenzylideneamino)-2H-chromen-2-one (HBC), has been synthesized by condensing salicylaldehyde with 6-aminocoumarin. The molecular structure of HBC has been determined by a single crystal X-ray analysis. It was established that in the presence of Al3+, HBC shows 25 fold enhancement of fluorescence intensity which might be attributed to the chelation-enhanced fluorescence (CHEF) process. HBC binds Al(NO3)3 in a 1 : 1 stoichiometry with a binding constant (K) of 7.9 × 104 M−1. Fe3+ and Mn2+ quench the emission intensity of the [HBC + Al3+] system to an insignificant extent at a concentration 10 times higher compared to that of Al3+. HBC is highly efficient in the detection of intracellular Al3+ under a fluorescence microscope.
Guha, S., Lohar, S., Sahana, A., Banerje, A., Safin, D., Babashkina, M. G., Mitoraj, M. P., Bolte, M., Garcia, Y., Mukhopadhyay, S. K., & Das, D. (2013). A coumarin-based “turn-on” fluorescent sensor for the determination of Al3+: single crystal X-ray structure and cell staining properties. Dalton Transactions, 42, 10198-10207. https://doi.org/10.1039/C3DT51045J (Original work published 2013)