Synthesis and Structural Studies of Two New Anthracene Derivatives

Anthracene derivatives are an interesting class of compounds and modifications in the anthracene ring, producing different compounds with different properties. Structural analysis of anthracene derivatives with modifications in position 9,10 of the aromatic ring is necessary in order to obtain information about its properties. The introduction of groups with polar substituents increases the possibility to modify the molecule lipophilicity, corroborating its use as bioimaging probes. Anthracene derivatives are used in many biochemical applications. These compounds can react with molecular singlet oxygen [O2 (1Δg)], a reactive oxygen species, through the Diels–Alder reaction [4 + 2] to form the respective endoperoxide and to be used as a chemical trap in biological systems. Thus, the structural and crystalline characterizations of two anthracene derivatives are presented in this work to obtain information about their physical-chemical properties. The compounds were characterized by Fourier-transform infrared spectroscopy, thermogravimetric analyses and scanning electron microscopy. The molecular structures of the compounds were studied by the Density Functional Theory, M06-2X/6-311++G(d,p) level of theory in the gas phase. From the results obtained for the frontier molecular orbitals, HOMO and LUMO, and from the Molecular Electrostatic Potential map, it was possible to predict the chemical properties of both compounds. The supramolecular arrangements were also theoretically studied, whose molecules were kept fixed in their crystallographic positions, through the natural bonding orbitals analysis to check the stability of interactions and the quantum theory of atoms in molecules to verify the type of intermolecular interaction between their molecules, as well as how they occur