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Potential chiral fluorescent molecular probes based on an ?,?-unsaturated ketone for anion detection.

ABSTRACT: A series of potential chiral compounds containing an ?,?-unsaturated ketone was developed for anion detection. The interplay of compounds and biological momentous anions (Cl-, H2PO4-, I-, AcO-, HS-, F-, and Br-) was evaluated by UV-vis experiments, fluorescence experiments, and electrochemical tests. By comparison, compound 1 had the best selectivity and compound 5 had the strongest binding ability among the five compounds. And compound 5 had the highest sensitivity to H2PO4- among the measured anions, and it also can be applied to actual samples, the content of H2PO4- tested in the potassium dihydrogen phosphate fertilizer solution reached above 97.5% of the marked content, and the recovery rates were within the range of 98.5-99.1%, attesting that this method was reliable for the test of H2PO4- in fertilizer. Through HRMS titration, circular dichroism and optical rotation experiments, the probable interacted mechanism was proved that the interaction site was the C=C of the ?,?-unsaturated ketone structure. In addition, the interacted mechanism was researched from the perspective of chirality. Furthermore, theoretical investigation analysis was introduced to reveal that the roles of molecular frontier orbitals in molecular interplay were determined. Therefore, this series of potential chiral compounds has potential application prospects in anion recognition.

SUBMITTER: Li C

PROVIDER: S-EPMC6906485 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection.

Li Congshu C Liu Lixia L Pan Weitong W Chen Yanmei Y Shang Xuefang X Wang Yingling Y Wang Tianyun T Xu Xiufang X

Scientific reports 20191211 1

A series of potential chiral compounds containing an α,β-unsaturated ketone was developed for anion detection. The interplay of compounds and biological momentous anions (Cl-, H2PO4-, I-, AcO-, HS-, F-, and Br-) was evaluated by UV-vis experiments, fluorescence experiments, and electrochemical tests. By comparison, compound 1 had the best selectivity and compound 5 had the strongest binding ability ...[more]

PMID: 31827214

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Project description:Three symmetrical bis-aryl-α,β-unsaturated ketone derivatives, 2,6-di((E)-benzylidene)-cyclohexan-1-one (DBC), 2,6-bis((E)-4-chlorobenzylidene)cyclohexan-1-one (BCC), and (1E,1'E,4E,4'E)-5,5'-(1,4-phenylene)bis(2-methyl-1-phenylpenta-1,4-dien-3-one) (PBMP), have been prepared using the aldol condensation approach toward ketones having two enolizable sites. The structures of DBC, BCC, and PBMP have been resolved via spectrometric methods. Moreover, the crystal structure of PBMP is determined by the single-crystal X-ray diffraction (SC-XRD) technique, which revealed that the PBMP molecular assembly is stabilized by the intermolecular C-H···O bonding and C-O···π and weak T-shaped offset π···π stacking interactions. The Hirshfeld surface analysis (HSA) of the PBMP crystal structure was performed as well, and the results were compared with the results of DBC and BCC. The density functional theory (DFT) study results revealed that the longer conjugated molecule of PBMP has smaller but still quite significant HOMO-LUMO gaps compared to the smaller molecules of BCC and DBC. The natural population analysis (NPA) and natural bonding orbital (NBO) analysis were performed. Accordingly, the hydrogen bonding and dipole-dipole interactions stabilize the crystal structures of these compounds. Additionally, the NBO analysis showed numerous high-energy stabilizing interactions for the PBMP compound due to the presence of numerous delocalized and relatively easily polarizable π-electrons, thus implying its significant thermodynamic stability. According to the global reactivity parameter (GRP) analysis, the compounds BCC and DBC are relatively stable in redox processes and have high thermodynamic stability and relatively lower reactivity in general. The molecular electrostatic potential (MEP) analysis results imply potential formation of the intermolecular hydrogen bonding and dispersion interactions, which stabilizes the crystal structures of these compounds.

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Potential chiral fluorescent molecular probes based on an ?,?-unsaturated ketone for anion detection.

Publications

Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection.

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