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In this study, a novel pillar[5]arene-quinoline (P5-Q) as an organic material is used to fabricate Langmuir-Blodgett (LB) thin films and its organic vapor sensing properties have been investigated. The LB deposition process is characterized by UV-visible spectroscopy, atomic force microscopy (AFM), scanning electron microscopy (SEM) and quartz crystal microbalance (QCM) techniques. The typical frequency shift per layer is obtained as 31.75 Hz per layer and the deposited mass onto a quartz crystal is calculated to be 539.69 ng per layer (2.03 ng mm). The fitted surface plasmon resonance (SPR) data were utilized to calculate the film thickness of this material. The thickness of a single layer is calculated to be 1.26 ± 0.09 nm. QCM and SPR systems are used to investigate gas sensing performance of macrocyclic LB films during exposure to Volatile Organic Compounds (VOCs). The macrocyclic LB thin films are more sensitive to dichloromethane than that of other vapors used in this study. The sensitivity and detection limit performance of the P5-Q QCM sensor to dichloromethane vapor were calculated to be 14.751 Hz ppm and 0.203 ppm, respectively. These results demonstrated that the P5-Q material is promising as an organic vapor sensing device at room temperature. Despite Langmuir-Blodgett being a traditional technique in colloid and interface science, this study presents the first gas sensor application for pillararene LB films. Because of the unique symmetric pillar architecture of P5-Q, self-assembly of pillar[5]arene molecules should afford various characteristic nanometer-scale architectures such as micelles, vesicles, and tubes.