In this paper, we report a novel imino bridged pillar[5larene derivative (P5N) for the first time. Four conformers (P5N0, P5N1, P5N12, and P5N13, arising due to the different orientation of N-H bond of imino bridging group) are obtained by quantum chemical calculations at the CAM-B3LYP/6-31+G(d,p) level of theory. The geometries, energies, electronic structures, and absorption spectra of P5N conformers as well as pillar[5]arene (P5) are discussed in detail. The inclusion complexes of paraquat (Pq) with P5N and P5, respectively, are also obtained at the same level of theory. Compared to P5, P5N exhibits better performance in inclusion complexation toward Pq. (C) 2016 Elsevier B.V. All rights reserved.