1,5-Benzodiazepin-2-ones: Investigation of a Family of Photoluminescent Materials

Abstract

Photoluminescent materials, that are now ubiquitous in our everyday life, have particularly attracted the attention of the scientific community these past few years due to potential important applications such as in bioimaging, sensing, or optoelectronics. In this context, relatively few different families of molecules have been reported to exhibit fluorescence in the aggregated or solid-state through the excited-state intramolecular proton transfer (ESIPT) photochemical process. The preparation and subsequent determination of photochemical properties of an underexplored family of 1,5-benzodiazepin-2-one derivatives are reported. From these data and X-ray diffraction analysis study, it emerged that photoluminescence (in the range 520-655 nm) was mostly attributed to ESIPT. The photoluminescent potential of 1,5-benzodiazepin-2-ones, their facile access, and functionalization were demonstrated through the preparation of two fluorogenic probes for the selective detection of biothiols.

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 .…”

“…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 . Indeed, obtained compound has been used to design two fluorogenic probes for the selective detection of biothiols . From a structural point of view, it seems that compound 1 establishes strong intramolecular and intermolecular O‐H…N and N‐H…O hydrogen bonds.…”

“…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 . Indeed, obtained compound has been used to design two fluorogenic probes for the selective detection of biothiols .…”

“…Chemical preparations of compounds 1 and 2 have been previously reported by our research group, and X‐ray analysis was only performed to confirm the stereochemistry of the products. Herein, crystalline structures have been fully described based on the SCXRD results.…”

“…All DFT calculations were performed starting from the experimental single‐crystal X‐ray data (crystallographic information files), reported by one of the authors of the present work, as input geometries. The geometry optimizations of different isolated monomer and their dimer models were accomplished in the gas using Gaussian 09, Rev D.01 software package .…”