This study reports the synthesis and photophysical characteristics of a new series of twelve ( Z )-2-(3,3,3-trifluorochloro-2-oxopropylidene)-2,3-dihydrobenzo e 1,4oxazepin-5(1 H )-ones (benzoxazepinones) from the cyclocondensation reaction of a series of 4,5-substituted 2-aminobenzoic acid with ( E )-5-bromo-1,1,1-trifluorochloro-4-methoxypent-3-en-2-one (5-bromo enones), with yields up to 86%. The structural elucidation of the reaction products was performed through multinuclear NMR, SC-XRD, and HRMS techniques. Regarding the photophysical properties of the studied molecules, the derivatives exhibited weak emission in solution, with enhanced luminescence in the solid state. Furthermore, interactions with biomacromolecules (DNA and BSA) were investigated, showing that the trichloroacetyl substituted derivatives of the 5a-f series exhibited higher binding and interaction values with nucleic acids and albumin. • A new series of benzoxazepinones were obtained in good yields. • Benzoxazepinones exhibited enhanced luminescence in the solid state. • Binding assays of derivatives with CT-DNA showed interaction at minor groove. • Products are potential photophysical probes or prototype bioactive agents. • Derivatives containing the -CCl₃ group have a slightly higher affinity for BSA.
Camargo et al. (Wed,) studied this question.