Abstract
A series of new compounds (1–12) containing 1,5-diaza-fluorenone, 1,10-phenanthroline-5,6-dione, ferrocene-1,1ʹ-dione, anthracene-9-carbaldehyde have been synthesized and optimized. The nanomaterials were also developed successfully. The binding properties were evaluated for biologically important anions (F−, Cl−, Br−, I−, AcO−, and H2PO4−) by theoretical investigation, UV-vis, and fluorescence experiments, and compound 6 displayed the strongest binding ability for AcO− ion among the synthesized compounds. Theoretical investigation analysis revealed that the intramolecular hydrogen bond existed in the structure of compound 6 and the roles of molecular frontier orbitals in molecular interplay. In addition, compound 6 showed wide antibacterial activity for colon bacillus, typhoid bacillus, and Pseudomonas aeruginosa, and inferior activity for hay bacillus and Staphylococcus aureus. This series of acylhydrazone nanomaterials showed double properties, anion binding ability, and antibacterial activity.
Highlights
Selective recognition and sensing of biologically important anions has attracted considerable attention in the field of supramolecular chemistry because of its important roles in medical, biological, chemical, and environmental systems [1,2,3,4,5,6,7,8,9,10]
Bearing the above considerations in mind, in this paper we report the synthesis of benzoylhydrazine derivatives and their properties containing antibacterial activity and anion binding ability (Scheme 1)
For compound 1, the highest occupied molecular orbital (HOMO) density was mainly localized on the 5-diaza-fluorenone moiety, while the lowest unoccupied molecular orbital (LUMO) density was localized on the whole molecular, which demonstrated that it was the electron transition of HOMO to arouse the red-shift phenomenon in the UV-vis spectra of host–guest
Summary
Selective recognition and sensing of biologically important anions has attracted considerable attention in the field of supramolecular chemistry because of its important roles in medical, biological, chemical, and environmental systems [1,2,3,4,5,6,7,8,9,10]. The importance of the selective detection of carboxylate and phosphorylated biomolecules probably surpasses that of other biologically functional anions. The focus has mainly been on the design of a receptor that has the ability to recognize and bind the biologically important anions. The synthesis and biological properties of hydrazine derivatives attracted the attention of many scholars. Almost no studies about anion binding ability based on acylhydrazone derivatives are currently being reported. Bearing the above considerations in mind, in this paper we report the synthesis of benzoylhydrazine derivatives and their properties containing antibacterial activity and anion binding ability (Scheme 1). The obtained experimental results showed that compound 6 (phenanthroline hydrazide derivative) could effectively recognize and sense AcO− in DMSO.
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