Mechanochemical and solution syntheses of two novel cocrystals of orcinol with two N,N′-Dipyridines: Structural diversity with varying ligand flexibility

Rautenberg, Max; Bhattacharya, Biswajit; Akhmetova, Irinia; Emmerling, Franziska

doi:10.1016/j.molstruc.2020.128303

Cited by 1 publication

(2 citation statements)

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“…3,5-dihydroxytoluene is known as an orcinol compound. Orcinol derivatives have important roles in many applications, such as for pharmaceutical and medical functions [22][23][24][25][26][27]. Among orcinol crystal structures, there are many polymorphs, pseudopolymorphs, and co-crystals of orcinols with different co-formers such as urea, acridine, and 4-cyanopyridine.…”

Section: Introductionmentioning

confidence: 99%

“…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 other co-crystal of an orcinol with 1,2-di(4pyridyl)ethylene is formed by a 0D four component complex through hydrogen bonds [23]. The advantage of crystals of orcinol compounds and their derivatives is that they allow for the design of synthetic sensors for anion detection.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection

et al. 2021

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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.

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