Three dimensional calixarene and oxa-calixarene scaffolds received considerable attention in complexation of various small molecules and ions. Yet, applying this complexation to the design of new supramolecular chemo-sensors requires the development of efficient signal transduction methods. Seamless integration of macrocyclic receptor unit into calixarene cavities to obtain hybrid fluorescent host materials can significantly improve such a process. In this proposal, we plan to synthesize novel calixarene capped conjugated macrocyles and establish their compatibility with efficient detection of important analyte molecules and ions in detail. The addition of photo-switchable, electron-donating, and electron-accepting groups to the macrocyclic receptor's portion will aid in a thorough evaluation of the novel compounds sensing capacities with different kinds of guest molecules. Smart fluorescent probes for use in molecular sensors, bioimaging, drug and gene delivery systems, self-assembled aggregates, and smart materials can be created by conjugating different fluorogenic groups to calixarene scaffolds. In addition, we plan to prepare and investigate anion-sensing properties of fluorescent oxa-calixarene scaffolds. We also intend to investigate the sensing properties of calixarene-containing electroactive polymers.