title: Synthesis and investigation of the properties of novel azocalix[4]arenes.
abstract: The azocalix[4]arenes molecules such as methylphenylazocalix[4]aren (MPcalix[4]) and methoxyphenylazocalix[4]aren (MOPcalix[4]) have been synthesized and characterized by experimental FT-IR and (1)H NMR spectral analyses. The fundamental vibrational transitions have been addressed by experimental FT-IR (4000-400 cm(-1)) technique and density functional theory (DFT) employing B3LYP level with the 6-31G(d) and 6-311G(d,p) basis sets. The (1)H NMR spectra of the studied compounds have been recorded in chloroform, and compared with computed data obtained by using gauge including atomic orbital (GIAO) method. Furthermore, thermodynamic properties (heat capacity, entropy, and enthalpy changes) and frontier molecular orbitals of the molecules in the ground state have been calculated by using the same method and basis sets. The non-linear optical properties such as the first order hyperpolarizability (β0), related properties (α0 and Δα) are also computed. Information about the charge density distribution of the molecules and its chemical reactivity has been studied by mapping molecular electrostatic potential surface (MEPs). The scaled vibrational frequency values have been compared with experimental FT-IR spectroscopic data. The correlations between the observed and calculated frequencies are in good agreement with each other as well as the correlation of NMR data. The linear polarizability and first hyperpolarizability of the studied molecules indicate that the compounds are a good candidate of nonlinear optical materials.
authors: Department of Physics, Pamukkale University, 20017, Kinikli, Denizli, Turkey.
authors: H H
authors: HH
authors: Kart
authors: Department of Physics, Pamukkale University, 20017, Kinikli, Denizli, Turkey.
authors: A
authors: A
authors: Bayrakdar
authors: Department of Chemical Engineering, Pamukkale University, 20017, Kinikli, Denizli, Turkey.
authors: S
authors: S
authors: Elcin
authors: Department of Chemical Engineering, Pamukkale University, 20017, Kinikli, Denizli, Turkey.
authors: H
authors: H
authors: Deligoz
authors: Department of Mechatronics Engineering, H.F.T. Technology Faculty, Celal Bayar University, 45400, Turgutlu, Manisa, Turkey. Electronic address: mehmet.karabacak@cbu.edu.tr.
authors: M
authors: M
authors: Karabacak
mesh_terms: D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D006841:Hydrocarbons, Aromatic
keywords: Calixarene; DFT; FT-IR and NMR spectra; HOMO–LUMO; NLO and MEP