title: The Synthesis and Anion Recognition Property of Symmetrical Chemosensors Involving Thiourea Groups: Theory and Experiments.
abstract: The synthesis of four symmetrical compounds containing urea/thiourea and anthracene/nitrobenzene groups was optimized. N,N'-Di((anthracen-9-yl)-methylene) thio-carbonohydrazide showed sensitive and selective binding ability for acetate ion among the studied anions. The presence of other competitive anions including F(-), H₂PO₄(-), Cl(-), Br(-) and I(-) did not interfere with the strong binding ability. The mechanism of the host-guest interaction was through multiple hydrogen bonds due to the conformational complementarity and higher basicity. A theoretical investigation explained that intra-molecular hydrogen bonds existed in the compound which could strengthen the anion binding ability. In addition, molecular frontier orbitals in molecular interplay were introduced in order to explain the red-shift phenomenon in the host-guest interaction process. Compounds based on thiourea and anthracene derivatives can thus be used as a chemosensor for detecting acetate ion in environmental and pharmaceutical samples.
authors.affiliation: Department of Chemistry, Xinxiang Medical University, Xinxiang 453003, China. shangxuefang@mail.nankai.edu.cn.
authors.forename: Xuefang
authors.initials: X
authors.lastname: Shang
authors.affiliation: Department of Chemistry, Xinxiang Medical University, Xinxiang 453003, China. YY851@xxmu.edu.cn.
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Yang
authors.affiliation: School of Pharmacy, Xinxiang Medical University, Xinxiang 453003, China. 15736991800@163.com.
authors.forename: Jiajia
authors.initials: J
authors.lastname: Fu
authors.affiliation: School of Pharmacy, Xinxiang Medical University, Xinxiang 453003, China. 15738671962@163.com.
authors.forename: Peipei
authors.initials: P
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, Nankai University, Tianjin 300071, China. xxfang@nankai.edu.cn.
authors.forename: Xiufang
authors.initials: X
authors.lastname: Xu
mesh_terms: D000085:Acetates / Q000032:analysis / Q000737:chemistry; D000838:Anions / Q000032:analysis / Q000737:chemistry; D000873:Anthracenes / Q000737:chemistry; D002623:Chemistry Techniques, Analytical / Q000379:methods*; D008958:Models, Molecular; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000085:Acetates; D000838:Anions; D000873:Anthracenes; C034020:anthracene; D013890:Thiourea
keywords: chemosensor; symmetrical structure; theoretical investigation; thiourea derivative