The synthesis, spectroscopic data and crystal and molecular structures of four 3-(3-phenylprop-1-ene-3-one-1-yl)thiophene derivatives, namely 1-(4-hydroxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H10O2S, (1), 1-(4-methoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C14H12O2S, (2), 1-(4-ethoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C15H14O2S, (3), and 1-(4-bromophenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H9BrOS, (4), are described. The four chalcones have been synthesized by reaction of thiophene-3-carbaldehyde with an acetophenone derivative in an absolute ethanol solution containing potassium hydroxide, and differ in the substituent at the para position of the phenyl ring: –OH for 1, –OCH3 for 2, –OCH2CH3 for 3 and –Br for 4. The thiophene ring in 4 was found to be disordered over two orientations with occupancies 0.702 (4) and 0.298 (4). The configuration about the C=C bond is E. The thiophene and phenyl rings are inclined by 4.73 (12) for 1, 12.36 (11) for 2, 17.44 (11) for 3 and 46.1 (6) and 48.6 (6)° for 4, indicating that the –OH derivative is almost planar and the –Br derivative deviates the most from planarity. However, the substituent has no real influence on the bond distances in the α,β-unsaturated carbonyl moiety. The molecular packing of 1 features chain formation in the a-axis direction by O—H...O contacts. In the case of 2 and 3, the packing is characterized by dimer formation through C—H...O interactions. In addition, C—H...π(thiophene) interactions in 2 and C—H...S(thiophene) interactions in 3 contribute to the three-dimensional architecture. The presence of C—H...π(thiophene) contacts in the crystal of 4 results in chain formation in the c-axis direction. The Hirshfeld surface analysis shows that for all four derivatives, the highest contribution to surface contacts arises from contacts in which H atoms are involved.
The synthesis and crystal structure of a new thiophene monomer containing an additional rhodanine heterocycle are reported. The crystal packing is sustained by N—H⋯O, C—H⋯O, C—H⋯S and C—H⋯π interactions.
The content of this paper focuses/shed light on the effects of X (X = S in P1 and X = O in P2) in C 11 H 7 NSX and R (R = H in P3, R = OCH 3 in P4, and R = Cl in P5) in C 18 H 9 ON 2 S 2 -R on structural features and band gaps of the polythiophenes containing benzo[ d ]thiazole and benzo[ d ]oxazole by the Density Function Theory (DFT) method/calculation. The structural features including the electronic structure lattice constant (a), shape, total energy (E tot ) per cell, and link length (r), are measured via band gap (E g ) prediction with the package of country density (PDOS) and total country density (DOS) of material studio software. The results obtained showed that the link angle and the link length between atoms were not changed significantly while the E tot was decreased from E tot = – 1904 eV (in P1) to E tot = – 2548 eV (in P2) when replacing O with S; and the E tot of P3 was decreased from E tot = – 3348 eV (in P3) when replacing OCH 3 , Cl on H of P3 corresponding to E tot = – 3575 eV (P4), – 4264 eV (P5). Similarly, when replacing O in P1 with – S to form P2, the E g of P1 was dropped from E g = 0.621 eV to E g = 0.239 eV for P2. The E g of P3, P4, and P5 is E g = 0.006 eV, 0.064 eV, and 0.0645 eV, respectively. When a benzo[ d ]thiazole was added in P1 (changing into P3), the E g was extremely strongly decreased, nearly 100 times (from E g = 0.621 eV to E g = 0.006 eV). The obtained results serve as a basis for future experimental work and used to fabricate smart electronic device.
The title compound, C 11 H 7 NS 2 , was prepared in high yield (87%) using a solvent-free microwave-assisted synthesis. The structure shows whole-molecule disorder with occupancies for two orientations (A and B) of 0.4884 (10) and 0.5116 (10), respectively. The thiophene and benzothiazole rings are almost planar and make dihedral angles of 10.02 (18) and 12.54 (19) for orientations A and B, respectively. Slipped -stacking between the aromatic rings, together with C-HÁ Á Á, C-HÁ Á ÁS and C-HÁ Á ÁN interactions, result in a herringbone motif in the crystal packing.
The structure of the title compound (systematic name: N-{[(2-hydroxyphenyl)methylidene]amino}morpholine-4-carbothioamide), C12H15N3O2S, was previously determined (Koo et al., 1977) using multiple-film equi-inclination Weissenberg data, but has been redetermined with higher precision to explore its conformation and the hydrogen-bonding patterns and supramolecular interactions. The molecular structure shows intramolecular O—H...N and C—H...S interactions. The configuration of the C=N bond is E. The molecule is slightly twisted about the central N—N bond. The best planes through the phenyl ring and the morpholino ring make an angle of 43.44 (17)°. In the crystal, the molecules are connected into chains by N—H...O and C—H...O hydrogen bonds, which combine to generate sheets lying parallel to (002). The most prominent contribution to the surface contacts are H...H contacts (51.6%), as concluded from a Hirshfeld surface analysis.
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