A novel class of self-doping conjugated oligomers, E,E-2-(sulfoalkoxy)-5-alkoxy-1,4-bis [2-(2,4,6-trimethoxyphenyl) ethenyl]benzenes, is presented. The synthesis and spectroscopic characterisation of five such oligomers are described, and an electrochemical analysis using cyclic voltammetry is performed to determine the anodic peak potentials. A structural study is performed on six self-doping oligomers in which the structures and energies of the possible mono-molecular forms of the electrically conducting doped material are described and evaluated using Hirshfeld charges and the Quantum Theory of Atoms In Molecules.
(E,E)-1-[2-(4-Nitrophenyl)ethenyl]-4-[2-(2,4-dimethoxyphenyl)ethenyl]benzene was characterised by X-ray diffraction and shown to be dynamically disordered at room temperature. The structure was re-determined over a range of temperatures to infer the thermodynamic parameters related to this disorder. A phase transition of third order according to the Ehrenfest classification scheme was discovered. To the best of our knowledge, this is the first experimentally observed phase transition of formal third order. It can be explained by the involvement of long-range lattice vibrations.
The crystal structure of the title compound, C25H23NO5, is centrosymmetric; it crystallizes in ribbons interacting through C—H⋯π contacts and C—H⋯O hydrogen bonds.
In the crystal of the title compound, C15H8N4O6, the molecules are organized in layers due to their linkage by weak C—H⋯N hydrogen bonds. The layers are themselves interconnected by weak C—H⋯O hydrogen bonds and π–π interactions [centroid–centroid distances = 3.8690 (15) and 3.9017 (16) Å]. The dihedral angle between the rings is 31.9 (1)°.
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