Synthesis, characterization, and computational study of a new zinc derivative (4.4′diaminodiphenylmethane) (meso-tetratolylporphyrinato) zinc {[Zn(TTP) (DADMP)2]}n

Highlights: • (4.4′diaminodiphenylmethane) (meso-tetratolylporphyrinato) zinc {[Zn (TTP) (DADMP)₂]}_nwas synthesized. • Density functional theory calculations were carried out. • (I)-(III)were studied using UV–vis, FT-IR,¹H NMR, fluorescence spectroscopy, and ESI. • Strong interaction between [Zn (TTP)] and DADMP ligand was proved. In this work, free base meso-tetratolylporphyrin H₂TTP (I), meso-tetratolylporphyrinato zinc(II) [Zn (TTP)] (II), and zinc derivative (4.4′diaminodiphenylmethane) (meso-tetratolylporphyrinato) zinc {[Zn (TTP) (DADMP)₂]}_n (III) were successfully synthesized and characterized. Density functional theory calculations at B3LYP-D3/6-311+G (d, p) level of theory were carried out for geometric parameters. Structures of compounds (I)-(III) were studied using UV–vis, FT-IR, ¹H NMR, fluorescence spectroscopy, and ESI Mass Spectrometry. The experimental data displayed good agreement with DFT-calculations results. Natural bond orbital (NBO) confirmed the stability of the obtained molecules from hyperconjugation interaction and charge delocalization. Molecular electrostatic potential (MEP) demonstrated the charge transfer and the way of interaction for (I)-(III). Frontier molecular orbitals (FMOs) showed the occurrence of charge transfer within the molecule. The optical spectra and interaction energy data confirmed a strong interaction between [Zn (TTP)] and DADMP ligand. The single structure of complex (III) indicated a building block, in solid state. The axial ligand (4.4′diaminodiphenylmethane) present as a bridge between adjacent zinc(II) consisted of 1D polymer chain along the [001] direction. The supramolecular was stabilized by weak intermolecular interactions C69–H69 … Cg7. The porphyrin core structure was practically quasi-plane. The optical spectra and interaction energy data proved the strong interaction between [Zn (TTP)] and DADMP ligand.