Solution and solid-state fluorescence of 2-(2′-hydroxyphenyl)-1,5-benzodiazepin-2-one (HBD) borate complexes

Abstract

International audienceA new family of fluorescent 1,5-benzodiazepin-2-one (HBD) borate complexes was prepared in good yields, and fully characterized by means of MS, NMR and IR spectroscopy, as well as X-ray crystal structure analysis for compound 13. Unlike their uncomplexed congeners, most of these cyclic boranils were emissive both in solution and the solid state, with maxima in the range of 426–596 nm. A systematic study of substituent effects revealed that the presence of a halogen atom specifically at position 8 of the fused-aromatic ring system led to an increase in fluorescence intensity in solution while electron rich substituents tended to extinguish the photoluminescence. Finally, a proof-of-concept study highlighted that the amide moiety of the benzodiazepinone framework could be functionalized with a chemical handle useful for subsequent specific modifications

Donor–Acceptor Boron-Ketoiminate Complexes with Pendent N-Heterocyclic Arms: Switched-on Luminescence through N-Heterocycle Methylation

“…In each structure, the boron center is monomeric and four-coordinate. Consistent with literature boron complexes supported by ketoiminate ligands, ,− the B–N bonds (1.562 Å average) are ∼0.09 Å longer than the B–O bonds (1.469 Å; Table ). Compared with symmetric boron diketonates and diiminates, the BF 2 unit is displaced further away from the plane of the chelate ring and the F–B–F angle more acute.…”

Crystallographic and first‐principles density functional theory study on the structure, noncovalent interactions, and chemical reactivity of 1,5‐benzodiazepin‐2‐ones derivatives

“…Among these molecules is benzodiazepines, sometimes called “benzos,” a class of psychoactive drugs whose core chemical structure is the fusion between the benzene and diazepine ring systems . Besides their significant medicinal and pharmacological applications, containing 1,5‐benzodiazepines derivatives, have also been reported to exhibit noteworthy photophysical properties . In this context, Hasan and coworkers (our collaborators in present work) were previously performing the preparation of photoluminescent material 4‐(2′‐hydroxyphenyl)‐1,5‐benzodiazepin‐2‐one compound 1, which manifested very interesting anticonvulsant and hypnotic activities .…”

Regioselective One-Pot Synthesis, Biological Activity and Molecular Docking Studies of Novel Conjugates N-(p-Aryltriazolyl)-1,5-benzodiazepin-2-ones as Potent Antibacterial and Antifungal Agents

“…Thus, and as a continuation of our ongoing research to synthesize novel 1,5-benzodiazepines derivatives bearing a triazole moiety [25], we turn our attention to designing novel hybrid conjugates of 1,2,3-triazoles tethered to 1,5-benzodiazepines namely the N-triazolo-1,5-benzodiazepin-2-ones. On the other hand, the click chemistry methodology is one of the most used strategies for simple access to these compounds, particularly the Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC) [26].…”