The present work explores the synthesis and characterization of antipyrine crowned Organosilatranes from a condensation reaction between antipyrine and amino silane followed by transesterification reaction with tripodal ligand. A highly selective chemosensor based on the prepared antipyrine crowned Organosilatrane exhibited remarkable selectivity and sensitivity towards Fe2+ and Hg2+ ions. The sensor binds to these ions at 1 : 1 stoichiometry and with high affinity as determined by Jobs plot and apparent from binding constant values of 4.05 ×105 M−1and 3.79 ×105 M−1 respectively. The structure of newly synthesized silanes and Organosilatranes were corroborated by numerous spectroscopic techniques. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim