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

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.