This paper reports a new approach towards the construction of a multifunctional periodic mesoporous organosilica (PMO), which integrates a range of advantages, such as mesoporous structural order, selective nucleobase-recognition properties, stimuli-responsive site-specific delivery of anticancer agents to cancer tissues, and Cu2+ adsorption, into a single entity. First, the appropriate organic-functional-receptor precursor was synthesized by a chemical process and used to fabricate a multifunctional pyridine-containing PMO material (DMPy-PMO) by a hydrolysis and condensation route. The designed organic-inorganic hybrid mesoporous silica chemosensor showed an intrinsic selective recognition of nucleobase, specifically thymidine, through multipoint hydrogen-bonding interactions with suitably arrayed receptor sites loaded into the rigid silica framework. An in vitro cytotoxicity test showed that the designed chemosensor materials have good biocompatibility and, therefore, could be promising candidates for the delivery of a range of therapeutic agents. Confocal laser scanning microscopy (CLSM) confirmed that the material can be internalized effectively by cancer cells (MCF-7 cells). In addition, the DMPy-PMOs showed efficient Cu2+ ion removal capacity at pH 5.0 with significantly high levels of adsorption (0.95 mmolg-1). These results suggest that the prepared multifunctional PMO hybrid has potential use as a smart material for a range of applications, such as biomolecule recognition, biomedical applications, and as an efficient adsorbent for the removal of metal ions.