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Anthracene-tethered aminomethyl oxadiazole chemosensor: a probe offering selective chromo- and fluorogenic signalings for targeting Cu(II)

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Abstract

A new optical chemosensor featuring anthracene as a fluorophore and an aminomethyl oxadiazole moiety as a bidentate chelate has been synthesized. From photophysical studies, we find the probe to offer remarkably selective chromo- and fluorogenic signaling responses towards biologically and environmentally significant Cu2+. In the presence of Cu2+, fluorescence is quenched to the extent of 95%, while the absorbance due to the anthracene chromophore is nearly completely bleached out. On the other hand, Li+, Na+, K+, Ba2+, Ca2+, Zn2+, Mg2+, Cd2+, Co2+, Ni2+, Ag+, Pb2+ and Hg2+ even at 10 times higher concentration than Cu2+ do not cause detectable photophysical perturbations. The stability constants, logK for Cu2+ were calculated to be 4.36 and 4.76 on the basis of spectrophotometric and fluorimetric titrations, respectively. However, logKs for other metal ions are too low (<0.1) to pose any interferences in the optical detection of Cu2+. Though, not fully defined, the uncommon phenomenon of the absorbance bleaching by Cu2+ is tentatively explained by invoking the involvement of non-covalent anthracene-Cu2+ complex.

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Acknowledgments

Thanks are due to the B.R.N.S., Government of India for generous financial support and the UGC for providing research fellowship to R. B. and M. C.

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  1. Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (E), Mumbai, 400098, India

    Sabir H. Mashraqui, Tabrez Khan, Mukesh Chandiramani, Rupesh Betkar & Kiran Poonia

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  1. Sabir H. Mashraqui
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Correspondence to Sabir H. Mashraqui.

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Mashraqui, S.H., Khan, T., Chandiramani, M. et al. Anthracene-tethered aminomethyl oxadiazole chemosensor: a probe offering selective chromo- and fluorogenic signalings for targeting Cu(II). J Incl Phenom Macrocycl Chem 67, 361–367 (2010). https://doi.org/10.1007/s10847-009-9717-4

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