title: Design of [2]rotaxane through image threshold segmentation of electrostatic potential image.
abstract: An electrostatic potential (ESP)-based image segmentation method has been used to estimate the ability of proton donation and acceptance involved in ring-rod recognition. The relative binding strength of [2]rotaxane has also been further estimated from the difference of the characteristic image-segmentation derived ESP between proton donor and proton acceptor. The size and electrostatic compatibility criteria are introduced to guide the design of interlocked [2]rotaxane. A library of 75 thermodynamically stable [2]rotaxane candidates has been generated, including 16 experimentally known systems. The theoretical results for 16 experimentally known [2]rotaxanes are in good agreement with both the experimental association constants and density functional theory-calculated binding energies. Our ESP-based image segmentation model is also applicable to the tristable [2]rotaxane molecular shuttle as well as [1]rotaxane with self-inclusion function, indicating this simple method is generic in the field of constructing other supramolecular architectures formed with donor/acceptor molecular recognition. © 2016 Wiley Periodicals, Inc.
authors.affiliation: School of Chemistry and Chemical Engineering, Key Laboratory of Mesoscopic Chemistry of MOE, Nanjing University, Nanjing, 210093, People's Republic of China.|School of Materials Science and Engineering, Jingdezhen Ceramic Institute, Jingdezhen, 333403, People's Republic of China.
authors.forename: Pingying
authors.initials: P
authors.lastname: Liu
authors.affiliation: School of Information Science and Engineering, Central South University, Changsha, 410083, People's Republic of China.
authors.forename: Qiufeng
authors.initials: Q
authors.lastname: Chen
authors.affiliation: School of Chemistry and Chemical Engineering, Key Laboratory of Mesoscopic Chemistry of MOE, Nanjing University, Nanjing, 210093, People's Republic of China.
authors.forename: Jing
authors.initials: J
authors.lastname: Ma
keywords: [2]rotaxane; binding strength; electrostatic potential; image segmentation; theoretical design