The synthesis, characterization, crystal structure and theoretical calculations of a new meso-BOBIPY substituted phthalonitrile

A novel 4-(2-meso-BOBIPY-phenoxy)phthalonitrile (6) derivative has been synthesized starting from BF3-OEt2 complex and 4-(2-meso-dipyrromethene-phenoxy)phthalonitrile (5) which was prepared by the oxidation of 4-(2-meso-dipyrromethane-phenoxy)phthalonitrile (4). The final product exhibit noticeable spectroscopic properties which were examined by its absorption and fluorescence emission spectra. The original compounds prepared in the reaction pathway were characterized by the combination of FT-IR, 1H and 13C NMR, UV-vis, MS and HRMS spectral data. The final product (6) was obtained as single crystal which crystallized in the triclinic space group P-1 with a=7.9411 (6) Å, b=9.0150 (6) Å, c=14.419 (1) Å, α=74.917 (5)°, β=86.824 (6)°, γ=84.109 (5)° and Z=2. The crystal structure has intermolecular C-H···F-B and C-H···N interactions. These interactions construct bifurcated hydrogen bonds in the crystal structure. In this study, It has been calculated; molecular structure, vibrational frequencies, 1H and 13C NMR chemical shifts and HOMO and LUMO energies of the title compound by using B3LYP method with 6-311++G(dp) basis set, and the electronic spectral characterization was investigated for the target product, as well.