Dessingou, Jayaraman ; Tabbasum, Khatija ; Mitra, Atanu ; Hinge, Vijaya Kumar ; Rao, Chebrolu P. (2012) Lower rim 1,3-di{4-antipyrene}amide conjugate of calix[4]arene: synthesis, characterization and selective recognition of Hg2+ and its sensitivity towards pyrimidine bases Journal of Organic Chemistry, 77 (3). pp. 1406-1413. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo2022372
Related URL: http://dx.doi.org/10.1021/jo2022372
Abstract
Structurally characterized lower rim 1,3-di{4-antipyrene}amide conjugate of calix[4]arene (L) exhibits high selectivity towards Hg2+ among other biologically important metal ion, viz., Na+, K+, Ca2+, Mg2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+, Pb2+ and Ag+ as studied by fluorescence, absorption and ESI MS. L acts as a sensor for Hg2+ by switch-off fluorescence and exhibits a lowest detectable concentration of 1.87 ± 0.1 ppm. The complex formed between L and Hg2+ is found to be 1:1 based on absorption and fluorescence titrations and was confirmed by ESI MS. The coordination features of the mercury complex of L were derived based on DFT computations and found that the Hg2+ is bound through an N2O2 extending from both the arms to result in a distorted octahedral geometry with two vacant sites. The nanostructural features, such as, shape and size obtained using AFM and TEM distinguishes L from its Hg2+ complex and were different from those of the simple mercuric perchlorate. L is also suited to sense pyrimidine bases by fluorescence quenching with a minimum detection limit of 1.15 ± 0.1 ppm in case of cytosine. The nature of interaction of pyrimidine bases with L has been further studied by DFT computational calculations and found to have interactions through a hydrogen bonding and NH-pi interaction between the host and the guest.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 79201 |
Deposited On: | 24 Jan 2012 15:35 |
Last Modified: | 14 Jun 2012 10:02 |
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