Substituted boron subphthalocyanines – Prospective compounds for theranostics: Synthesis, photochemical properties and in vitro cytotoxicity

First Subphthalocyanine Analogue with Fused 6H‐1,4‐diazepine Ring and its Conversion to Aminobenzamide Derivative

“…The doublet at 8.1 ppm can be assigned to four o-protons and the multiplet at 7.5-7.6 ppm, to overlapping resonances of six m-and p-protons in two phenyl groups attached to the 1,4-diazepine ring. This assignment is confirmed by 2D 1 H- 13 C HSQC spectrum (Figure 5B). The intensity of the singlet at 7.86 ppm corresponds to one proton.…”

“…[43] In both cases the resonance of the carbon atom of the CH 2 group in tetra(6H-1,4diazepino)porphyrazines is observed at 35-45 ppm [42] similarly to its position in 2,4-diphenyl-3H-1,5benzodiazepine. [44] In the subporphyrazine from the 2 nd fraction the carbon atom in the 6-position is bonded only with one proton, and the downfield shift of its resonance to 65.58 ppm in the 13 C NMR spectrum indicates the presence of an electronegative neighboring atom. Considering the positive molecular ion peak at 777 Da in the mass spectra, this is consistent with the presence of the À HC 6 Cl-fragment appearing due to chlorination of 1,4-diazepine ring in the course of the reaction of dinitriles with BCl 3 .…”

“…In the last years, tremendous progress have been achieved in the study of axially/ peripherally modified subphthalocyanines and their hybrids as active components in organic electronics, [9,10] photocatalysis, [11,12] and theranostics. [13,14] Functionalization of the [sPc] macrocycle is not limited to introduction of appropriate substituents in benzene ring(s). Alternatively they can be exchanged by aromatic heterocycles when corresponding heterocyclic dicarbonitriles are used along with or instead of phthalonitriles in template co-cyclotrimerization in the presence of boron(III) halide as templating agent.…”

“…The variety of such methods allows fine‐tuning of the photophysical properties, spectral and redox characteristics for high efficiency in different applications. In the last years, tremendous progress have been achieved in the study of axially/peripherally modified subphthalocyanines and their hybrids as active components in organic electronics, [9,10] photocatalysis, [11,12] and theranostics [13,14] …”

Subphthalocyanine-flipper dyads for selective membrane staining

“…Regarding the photophysical properties, SubPcs are particularly attractive because of their high molar extinction coefficients, as well as sharp peaks of absorption (570–580 nm) and emission (585–600 nm), with small Stokes shift, thus short lifetimes. 23 Moreover, their absorption and emission bands overlap with the respective bands of HydroFlippers (420–500 nm absorption, 590–750 nm emission), allowing their co-excitation and bidirectional FRET without undesired shifts. Therefore, the combination of SubPcs and HydroFlippers in dyads (such as 1) was of interest to allow internal calibration, since the presence of the probe inside the membrane is clearly demonstrated, which complemented the environment-sensitive probe with varying fluorescence lifetime with an environment-insensitive probe of short lifetime.…”