Abstract
In this study, 2-(3-(hexyloxy)-5-methylphenoxy)-N-(4-nitrophenyl)acetamide (sensor L1) was synthesized and characterized by FT–IR, ESI–MS, 1H and 13C NMR spectroscopy, elemental analysis, and single crystal X-ray techniques. The crystal structure and space group of sensor L1 was monoclinic and P21, respectively. The crystal packing of sensor L1 was dominantly linked by two strong hydrogen bonds forming a six membered ring pattern. The binding properties of sensor L1 and various anions (F−, Cl−, Br−, CH3COO−, C6H5COO−, and H2PO4−) were investigated by UV–Vis and 1H NMR spectroscopy in DMSO. The proton resonance signals of sensor L1 and F− greatly changed positions when compared to those of anions. The solution color of sensor L1 changed from pale yellow to orange in the presence of F−. The UV–Vis results indicate that sensor L1 and F− ions underwent an internal charge transfer process. The stoichiometric complex was confirmed by Job’s method, revealing a 1:1 formation for sensor L1 and fluoride. Our results show that sensor L1 is highly selective for fluoride ions over other anions.
Highlights
Anion sensors have been the subject of considerable interest for their numerous roles in various processes in the fields of biology, catalysis, industry, and environmental protection
An isosbestic point at 378 nm indicated that the two formations of sensor L1 were normal and deprotonated species in the equilibrium [37,38]. These results indicate that the mechanism of sensor L1 and F− ions occurred under an internal charge transfer process [39]
The crystal structure revealed that the planes of the two functional groups were almost coplanar with the plane of toluene
Summary
Anion sensors have been the subject of considerable interest for their numerous roles in various processes in the fields of biology, catalysis, industry, and environmental protection. There are many polymorphs, pseudopolymorphs, and co-crystals of orcinols with different co-formers such as urea, acridine, and 4-cyanopyridine. They exhibit three possible conformations (i.e., “anti-anti”, “syn-anti”, and “syn-syn”) through the packing modes of hydrogen bonds [28]. The co-crystal of an orcinol with 1,2-di(4-pyridyl)ethane can be observed in the pattern of 1D zig-zag chains that are interconnected to form a 2D layer structure by C–H–π and π–π interactions. The advantage of crystals of orcinol compounds and their derivatives is that they allow for the design of synthetic sensors for anion detection. We investigate the synthesis and crystallization of sensor L1, 2-(3-(hexyloxy)-5methylphenoxy)-N-(4-nitrophenyl)acetamide, containing 3,5-dihydroxytoluene as a backbone and amide moiety as a binding site for anions. The complexation studies between sensor L1 and different anions were conducted using 1 H–NMR and UV–Visible spectroscopy
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