1,8-Naphthalimides 3-substituted with imine or β-ketoenamine unit evaluated as compounds for organic electronics and cell imaging

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

“…The 1,8-naphthalimide derivatives described in our publications were used for cellular imaging, including salicyl imine analogues undergoing hydrolysis [28] or were susceptible to aggregation-induced emission (the β-ketoenamines) [34,35]. In turn, the use of iminonaphthalimides in organic electronics included the structures of mono-and bis-iminonaphthalimides [33,35,36]. Most of the compounds tested showed the ability to electroluminescence, which is the first time our research showed this.…”

“…After 24 h, the complete DMEM was exchanged for solutions of AzNI compounds at concentrations ranging from 1 to 25 µM. After a 72 h incubation, the cytotoxicity assay-CellTiter 96 ® AQ ueous One Solution Cell Proliferation Assay-MTS (Promega, Medison, WI, USA)-was performed [28,35]. Briefly, the solutions of the tested AzNI compounds were removed, and 100 µL DMEM (without FBS and phenol red-PF) and 20 µL of MTS reagent were added and incubated for 1 h at 37 • C. Afterward, the optical densities of wells with controls (untreated cells) and tested compounds were measured at 490 nm using a multi-plate reader-Synergy 4 (BioTeK, Winooski, VT, USA).…”

“…The co-localization experiments with some changes were performed according to the protocol described in [35]. Briefly, MCF-7 cells were seeded in the same manner as described in Section 2.8.…”

“…In the case of azomethine with a hydroxyl group, the significance of the excited state intramolecular proton transfer (ESIPT) with protic solvents, with a tendency towards ACQ, was described [28], as well as the importance of the hydrolysis of this system related to the presence of an active site complexation [25,26,28]. In contrast, analogs containing a β-ketoenamine linkage showed a tendency towards AIE [35].…”

“…In our previous works, for the first time, our group described properties of the 3-C substituted 1,8-naphthalimides containing an imine and β-ketoamine bond, and their applicability in OLED devices and cell imaging [28,[33][34][35][36]. The 1,8-naphthalimide derivatives described in our publications were used for cellular imaging, including salicyl imine analogues undergoing hydrolysis [28] or were susceptible to aggregation-induced emission (the β-ketoenamines) [34,35]. In turn, the use of iminonaphthalimides in organic electronics included the structures of mono-and bis-iminonaphthalimides [33,35,36].…”