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The supramolecular approach plays a pivotal role in the construction of smart and functional materials due to the reversible nature of noncovalent interactions. In the present work, two compounds, cholesterol-functionalized calix[4]pyrrole (CCP) and perylene bisimide diacid (PDA), were synthesized. Little fluorescence is observed in the ethanol solution of the mixture of CCP and PDA, while the solution turns fluorescent upon introduction of ammonia, which is attributed to the formation of a supramolecular ensemble, PDA/(CCP)2/NH3. The fluorescence emission of the as-formed ensemble is sensitive to the presence of phenol, an electron-rich analyte. Interestingly, the sensing can also be observed in the film state, and the relevant detection limit (DL) is lower than 1 ppb. Moreover, the sensing could also be performed in a visualized manner. Upon the basis of the findings, a sensor device with instant response and good reversibility was developed. Further studies revealed that the as-developed fluorescent ensemble is also sensitive to the presence of TNT, an electron-poor compound. The DL for this sensing is ∼80 nM. To our knowledge, this is the first report that a fluorescent sensor could be used for phenol sensing in the vapor state, and for sensing of both electron-rich and electron-poor analytes in solution state. It is believed that the present study presents a distinctive example that demonstrates how smart sensing is realized via combination of the host–guest chemistry of calix[4]pyrrole and the aggregation and disaggregation property of PBI derivatives.