title: Understanding the relationships between molecule structure and imprinting effect of two acetyl-nitrogen heterocyclic compounds.
abstract: The molecularly imprinted polymers (MIPs) for two structural analogs, 1,3,5-triacetyl-1,3,5-triazacyclohexane (TRAT) and 1,3,5,7-tetraacetyl-1,3,5,7-tetraazacyclooctane (TAT), have been synthesized respectively under the same conditions. The TAT-MIP showed excellent imprinting effect, whereas the TRAT-MIP did not. To understand the different imprinting effects of the MIPs prepared from these two templates, the geometric structures and energetic properties of complexes formed around TAT and TRAT were studied computationally. The results indicate that in liquid phase, for the complexes formed with TAT and its nearest neighbor molecules, the magnitude of the binding energy increases with the number of surrounding TAT, methacrylic acid, and acetonitrile (ACT), whereas for the cases of TRAT, the magnitude of the binding energy increases with the number of surrounding TRAT and trimethylolpropane trimethacrylate. The studied systems form stronger and thus more stable networks encapsulating TAT than with TRAT. ACT may also play an important role in the polymerization phase in stabilizing the shapes of the cavities that TATs reside in. We propose these as the major factors that affect the different imprinting effects of the two MIPs. Copyright © 2016 John Wiley & Sons, Ltd.
authors.affiliation: Beijing Institute of Technology, Beijing, 100081, China.|Yan'an University, Yan'an, 716000, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Wang
authors.affiliation: Beijing Institute of Technology, Beijing, 100081, China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Dong
authors.affiliation: Beijing Institute of Technology, Beijing, 100081, China.
authors.forename: Min
authors.initials: M
authors.lastname: Xue
authors.affiliation: Beijing Institute of Technology, Beijing, 100081, China.
authors.forename: Xuemin
authors.initials: X
authors.lastname: Dong
authors.affiliation: Beijing Institute of Technology, Beijing, 100081, China.
authors.forename: Zhibin
authors.initials: Z
authors.lastname: Xu
authors.affiliation: Beijing Institute of Technology, Beijing, 100081, China.
authors.forename: Zihui
authors.initials: Z
authors.lastname: Meng
authors.affiliation: Nanjing University of Science and Technology, Nanjing, 210094, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Luo
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004735:Energy Transfer; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D054802:Molecular Imprinting / Q000379:methods*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D058105:Polymerization
chemical_list: D000097:Acetonitriles; D006571:Heterocyclic Compounds; D009584:Nitrogen; C032159:acetonitrile
keywords: 1,3,5,7-Tetraacetyl-1,3,5,7-tetraazacyclooctane; 1,3,5-Triacetyl-1,3,5-triazacyclohexan; DFT calculation; Imprinting effect; Molecularly imprinted polymers