How do fluoride ions bind to tetrathiacalix[2]arene[2]triazines?

Pisagatti, Ilenia; Manganaro, Nadia; Mirabella, Chiara F. M.; Pappalardo, Andrea; Sfrazzetto, Giuseppe Trusso; Nastasi, Francesco; Notti, Anna; Parisi, Melchiorre F.; Gattuso, Giuseppe

doi:10.1016/j.tetlet.2020.151911

Cited by 3 publications

(1 citation statement)

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“…Hence, thiacalixarenes show potential as highly useful molecular skeletons for porous molecular recognition materials [ 48 ]. Furthermore, a new breed of calixarene derivatives built with aromatic heterocycles, e.g., thiophene [ 49 , 50 , 51 ], dithienothiophene [ 52 ], pyridine [ 53 , 54 , 55 , 56 ], pyrimidine [ 57 ], and triazine [ 58 ], have been synthesized. These derivatives have attracted much attention due to their proper inclusiveness, electrochemical properties, and molecular geometries based on the introduction of heteroatoms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Characterization of Thiacalix[4]-2,8-thianthrene

2023

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Sulfur-containing macrocycles have attracted substantial interest because they exhibit unique characteristics due to their polygonal ring-shaped skeleton. In this study, a thianthrene-based cyclic tetramer with the sulfur linker, thiacalix[4]-2,8-thianthrene (TC[4]TT), was successfully prepared from a cyclo-p-phenylenesulfide derivative using acid-induced intramolecular condensation. Single crystal X-ray diffraction revealed that TC[4]TT adopts an alternative octagonal form recessed to the inner side. Its internal cavity included small solvents, such as chloroform and carbon disulfide. Due to its polygonal geometry, TC[4]TT laminated in a honeycomb-like pattern with a porous channel. Furthermore, TC[4]TT showed fluorescence and phosphorescence emission in a CH2Cl2 solution at ambient and liquid nitrogen temperatures. Both emission bands were slightly redshifted compared with those of the reference compounds (di(thanthren-2-yl)sulfane (TT2S) and thianthrene (TT)). This work describes a sulfur-containing thiacalixheterocycle-based macrocyclic system with intriguing supramolecular chemistry based on molecular tiling and photophysical properties in solution.

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