J. Appl. Cryst.の発刊に際して

A noncentrosymmetric chalcone derivative (E)-1-(thiophen-2-yl)-3-(3, 4, 5-trimethoxyphenyl) prop-2-en-1-one (TTMP) was synthesized using Claisen Schmidt condensation approach and single crystals were grown using slow evaporation method. The grown TTMP crystals crystallizes in orthorhombic structure with Pna21 space group. The intermolecular interactions of the TTMP crystals were envisioned by Hirshfeld surface analysis (HSA). Further, the structural conformations of the crystal were carried out by using 1H NMR, FTIR, and FT-Raman spectral analysis. The UV–Vis–NIR spectrum of the sample clearly shows the prime transparency in the entire visible and near infrared region. Thermal studies (TG/DTA/DSC) of the TTMP sample shows excellent thermal stability and phase transition and also noticed that crystal was most stable up to 152.65 °C. The second harmonic generation efficiency was obtained for the crystals using Nd:YAG laser and is to be 1.93 times that of urea. The third order nonlinear absorption coefficient (β), nonlinear refractive index (n2), third-order nonlinear susceptibilities (χ (3)), second order hyper polarizability (γh) and optical limiting thresholds were determined by Z-scan technique using the Diode-Pumped Solid State (DPSS) Continuous Wave (CW) laser. The results suggest that the TTMP molecules are promising materials for optoelectronic device applications.

Second and third order nonlinear optical studies of a novel thiophene substituted chalcone derivative

The mol­ecule of the title heteroaryl chalcone, C16H16O4S, which consists of substituted thio­phene and benzene rings bridged by the prop-2-en-1-one group, is slightly twisted. The dihedral angle between the thio­phene and 3,4,5-trimethoxy­phenyl rings is 12.18 (4)°. The three meth­oxy groups have two different conformations; two meth­oxy groups are coplanar [C—O—C—C torsion angles = −1.38 (12) and 0.47 (12)°] whereas the third is (-)-synclinal with the benzene ring. In the crystal structure, adjacent mol­ecules are linked in a face-to-side manner into chains along the c axis by weak C—H⋯O(enone) inter­actions. These chains are stacked along the b axis by weak C—H⋯O(meth­oxy) inter­actions.

https://journals.iucr.org/e/issues/2009/07/00/sj2627/sj2627.pdf

(E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Chalcones and their pyrazine analogs synthesized by Claisen–Schmidt condensation were tested for inhibition of aldose reductase, which is the key enzyme in the development of secondary diabetic complications. The most active compounds exerted IC50 values within the micromolar scale, and their interactions with the enzyme were described in a molecular docking study. Antioxidant activity of several representative compounds was explored in DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, revealing significant scavenging for 4-hydroxy-substituted derivatives endowed with electron-donating methoxy substituent in position 3 of the ring B. To conclude, the novel chalcones hydroxylated and methoxylated in the B-ring and their pyrazine analogs exhibited significant aldose reductase inhibition activity, albeit lower in comparison with the reference epalrestat. Medium antioxidant activity (not exceeding the antioxidant efficacy of the standard Trolox) was shown by the representative compounds tested.

Chalcones and their pyrazine analogs: synthesis, inhibition of aldose reductase, antioxidant activity, and molecular docking study

Three series of heteroaryl chalcones, (E)-1-(2-pyridyl)-3-(X)prop-2-en-1-one (Ia-Ic), (E)-1-(2-thienyl)-3-(X)prop-2-en-1-one (IIa-IIc), and (E)-1-(2-furyl)-3-(X)prop-2-en-1-one (IIIa-IIIc), where X = 2,4,5-trimethoxyphenyl (for series a), X = 2,4,6-trimethoxyphenyl (for series b), and X = 3,4,5-trimethoxyphenyl (for series c) were synthesised using basic catalysed aldol condensation and characterised using 1H NMR and FT-IR spectroscopies. Compound IIa was also characterised by single crystal X-ray analysis. The absorption and fluorescence emission spectra of these compounds revealed that the absorption and fluorescence depended on the heterocycle rings and trimethoxysubstituted phenyl rings linked to the enone system. The position of methoxy groups substantially affected the fluorescent properties. Compounds Ia-IIIa containing the 2,4,5-trimethoxyphenyl moiety exhibited the red-shift phenomenon and strong emission fluorescence.

Influence of trimethoxy-substituted positions on fluorescence of heteroaryl chalcone derivatives

In the title mol­ecule, C23H15BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9 (1) and 45.8 (1)°, respectively, with the 4-bromo­phenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52 (7)°. In the crystal structure, mol­ecules are linked into dimers by C—H⋯Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions involving the central benzene ring of the anthracene ring system.

https://journals.iucr.org/e/issues/2009/02/00/ci2756/ci2756.pdf

Paradorn Pakdeevanich

Papers

(E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

(E)-3-(Anthracen-9-yl)-1-(4-bromo-phen-yl)prop-2-en-1-one.