4-Formylphenyl-β-D-allopyranoside decorated diorganotin(IV) crystalline solid with chevron architecture: An effective water-stable adsorbent against aqueous organic dyes

Abstract

A glucosyl appended chromone-based diorganotin(IV) crystalline solid (DOC) is obtained from β-D-allopyranoside substituted 3-hydroxy-benzo-γ-pyrone. The combination of organotin(IV) unit, glucosyl substituent and chromone skeleton introduced some special features to the solid including controlled solubility, water stability, and plenty of interactive sites. The step-wise formation of products is supported by FT-IR spectroscopy, multinuclear NMR spectroscopy, CHN elemental analyses, mass spectrometry, scanning electron microscopy, thermal gravimetric analysis, and single-crystal X-ray diffraction analyses. The DOC molecules led to herringbone architecture via O–H···O, C–H·····Sn, C–H···O, C–H·····π, and π⋯π interactions, where each DOC molecule possessed “skew-trapezoidal bipyramidal” geometry. Furthermore, the DOC has been found efficient adsorbent for organic dyes with a partition coefficient of 793.3 mg g−1 μM−1 for Brilliant blue. The theoretical studies justified the highest adsorption of Brilliant blue due to the small value of the HOMO-LUMO energy gap (ΔE = 0.34 eV), the high value of electrophilicity index (ω = 40.64), and the low value of chemical hardness (η = 0.17 eV). The Langmuir model and pseudo-second-order model well-described the adsorption parameters like adsorption behaviour, diffusion, and removal rates of dyes. Based on the results, the DOC is expected as a viable option for the uptake of organic dyes from an aqueous solution.