Fused Selenazolinium Salt Derivatives with a Se–N⁺ Bond: Preparation and Properties

Abstract

Stimuli‐responsive metal–organic polyhedra (srMOPs) functionalized with azobenzene showed UV‐irradiation‐induced isomerization from the insoluble trans‐srMOP to the soluble cis‐srMOP, whereas irradiation with blue light reversed this process. Guest molecules were trapped and released upon cis‐to‐trans and trans‐to‐cis isomerization of the srMOPs, respectively. This study provides a new direction in the ever‐diversifying field of MOPs, while laying the groundwork for a new class of optically responsive materials.

Zero-, one-, two- and three-dimensional supramolecular architectures sustained by Se…O chalcogen bonding: A crystallographic survey

“…Firstly, solvates are described followed by co-crystals. The chemical structures of the 20 compounds covered in this section, 204 – 224 [118] , [233] , [234] , [235] , [236] , [237] , [238] , [239] , [240] , [241] , [242] , [243] , [244] , [245] are shown in Fig. 25 .…”

Selenazolinium Salts as “Small Molecule Catalysts” with High Potency against ESKAPE Bacterial Pathogens

“…Synthesis of 3-bromo-selenazolopyridinium chlorides 1 – 7 and 3-bromo-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3- b ]thiazolinium chloride 8 ( Figure 1 ) was described elsewhere [ 22 ].…”

“…The selenazolinium salts: 3-bromo-2-(1-hydroxy-1-methylethyl)[1,2]selenazolo[2,3- a ]pyridinium chloride ( 1 ), 3-bromo-2-(1-hydroxy-1-phenylethyl)[1,2]selenazolo[2,3- a ]pyridinium chloride ( 2 ), 3-bromo-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3- a ]pyridinium chloride ( 3 ), 3-bromo-2-(1-hydroxycyclohexyl)-5-methyl[1,2]selenazolo[2,3- a ]pyridinium chloride ( 4 ), 3-bromo-7-formyl-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3- a ]pyridinium chloride ( 5 ), 3-bromo-2-(1-hydroxycyclohexyl)-7-(2-hydroxypropan-2-yl)[1,2]selenazolo[2,3- a ]pyridinium chloride ( 6 ), 3-bromo-2-(1-hydroxycycloheptyl)[1,2]selenazolo[2,3- a ]pyridinium chloride ( 7 ), and 3-bromo-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3- b ]thiazolinium chloride ( 8 ) were synthesized according to the procedures described previously [ 22 ].…”

“…As part of this strategy, and during the search for new ebselen analogues containing fused rings with an endocyclic Se–N bond, a series of selenazolinium salts were obtained [ 22 ]. Eight of these compounds ( 1 – 8 , Figure 1 ), have been investigated here for their antibacterial properties against a variety of S. aureus clinical isolates, as well as representative strains of clinically relevant Gram-negative ESKAPE bacteria.…”

Small Molecule Catalysts with Therapeutic Potential

“…The reactivity of selenium in compounds, for instance in the isoselenazole ebselen, can also be improved considerably by placing a positive charge at the nitrogen in the selenium-nitrogen bond. As Arsenyans and his colleagues have shown, the resulting selenazolinium salts are incredibly reactive and also active against a wide range of cancer cell lines [ 98 ]. Similarly, Handzlik and her colleagues, employing the same palette of selenazolinium salts have demonstrated that such compounds also act against certain resistant strains of bacteria [ 59 ].…”