Study of self-assembly features in 4H-pyrans: Synthesis, Hirshfeld surface, and energy framework analysis

Lalhruaizela,; Marak, Brilliant N.; Hazarika, Biki; Pandey, Sunil; Kataria, Ramesh; Singh, Ved Prakash

doi:10.1016/j.molstruc.2022.133361

Cited by 7 publications

(8 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…DFT calculations were carried out to support the interpretation of the results concerning the optical properties of the studied ligands. Hirshfeld analysis extensively shows intramolecular interactions like it was observed for other compounds [ 37 , 38 ]. The emissive ligands cover by the spin coating and thermal vapor methods create thin fluorescent films.…”

Section: Introductionmentioning

confidence: 79%

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

et al. 2022

View full text Add to dashboard Cite

Two macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde L1 or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde L2, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, fluorescence and IR). X-ray crystal structure determination and DFT calculations for compounds confirmed their geometry in solution and in the solid phase. Moreover, intermolecular interactions in the crystal structure of L1 and L2 were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The 3D Hirschfeld analyses show that the most numerous interactions were found between hydrogen atoms. A considerable number of such interactions are justified by the presence of bulk tert-butyl groups in L2. The luminescence of L1 and L2 in various solvents and in the solid state was studied. In general, the quantum efficiency between 0.14 and 0.70 was noted. The increase in the quantum efficiency with the solvent polarity in the case of L1 was observed (λex = 350 nm). For L2, this trend is similar, except for the chloroform. In the solid state, emission was registered at 552 nm and 561 nm (λex = 350 nm) for L1 and L2, respectively. Thin layers of the studied compounds were deposited on Si(111) by the spin coating method or by thermal vapor deposition and studied by scanning electron microscopy (SEM/EDS), atomic force microscopy (AFM), spectroscopic ellipsometry and fluorescence spectroscopy. The ellipsometric analysis of thin materials obtained by thermal vapor deposition showed that the band-gap energy was 3.45 ± 0.02 eV (359 ± 2 nm) and 3.29 ± 0.02 eV (377 ± 2 nm) for L1/Si and L2/Si samples, respectively. Furthermore, the materials of the L1/Si and L2/Si exhibited broad emission. This feature can allow for using these compounds in LED diodes.

show abstract

Section: Introductionmentioning

confidence: 79%

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The mixture was then stirred using magnetic stirrer for 10 min at room temperature. The precipitate was filtered in a sintered glass funnel, washed with ice‐cold methanol, and then kept in a desiccator to obtain a pure product of 4H‐pyran derivatives [20,21] …”

Section: Methodsmentioning

confidence: 99%

“…It has been recently identified that calcium channels are potential targets for cancer therapy [19,20] . Similarly, PDE3 enzymes are overexpressed in many cancer cells [21] . Thus the synthesized compounds are designed based on the hybrid structural analogs of commercially available drugs such as nifedipine and milrinone, which are the calcium channel blocker and the PDE3 inhibitor.…”

Section: Introductionmentioning

confidence: 99%

“…In the present study, a new series of cyanopyridine-based dihydropyridones derivatives are synthesized. Motivated from our previous research, [2,[19][20][21] pyran derivatives bearing anisole and toluene moieties are converted to pyridone derivates in the current research. However, three pyran derivatives with 3-OCH 3 , 4-NO 2 , 2,5-OCH 3 possessing phenyl groups connected to the central pyran ring were not selected for this present study.…”

Section: Introductionmentioning

confidence: 99%

“…[19,20] Similarly, PDE3 enzymes are overexpressed in many cancer cells. [21] Thus the synthesized compounds are designed based on the hybrid structural analogs of commercially available drugs such as nifedipine and milrinone, which are the calcium channel blocker and the PDE3 inhibitor. And a prototype anticancer drug, monastrol, that inhibits the Eg5 protein was also regarded (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Non‐Covalent Interactions in the Self‐Assembly of Dihydropyridone Supramolecules and In Vitro Anti‐Cancer Assessment in Human Lung Adenocarcinoma Cell Line (A549)

et al. 2023

Self Cite

View full text Add to dashboard Cite

The synthesis of dihydropyridone derivatives has been reported by ring rearrangement of pyrans using iodine and formic acid as a catalyst separately. Dihydropyridones were crystallized subjected for single-crystal X-ray crystallography to acquire their structural parameters. The different non-covalent interactions involved within the supramolecular systems were studied and validated using Hirshfeld surface plot analysis. NÀ H•••O interactions between the lactam group dominate. Still, other non-covalent interactions such as CÀ Hand lone pair•••π systems act as the driving force in facilitating the self-assembly of the dihydropyridone supramolecules. The synthesized compounds were analyzed by in vitro techniques using human lung adenocarcinoma (A549) to evaluate their cytotoxic activities. Ethyl 4-(4-chlorophenyl)-5cyano-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate has shown the highest cytotoxicity among all the synthesized compounds. Molecular recognition properties of the dihydropyridone compounds were also studied, employing molecular docking tools to gain insight into the binding mode inside the allosteric binding pocket of the Eg5 protein through noncovalent interactions.

show abstract

Synthesis of Spirooxindoles and Study of their Self‐Assembly features; Hirshfeld Surface, Energy Framework andIn Silicoanalysis

et al. 2023

Self Cite

View full text Add to dashboard Cite

In this study, the 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitrile derivatives were synthesized, crystallized, and their molecular geometries were established by the SCXRD method. The significance of weak intermolecular interactions in the self‐assembly of 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitriles was then investigated. The supramolecular framework analysis indicated that 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitriles establish their network in self‐assembly mainly by N−H⋅⋅⋅O, N−H⋅⋅⋅N, C−H⋅⋅⋅O, C−H⋅⋅⋅C, C−H⋅⋅⋅N, and C−H⋅⋅⋅π interactions. The energy framework analysis revealed the dominant contribution of electrostatic energy in the crystal packing of the titled compounds. The PASS prediction of the titled compounds has shown a reasonably good affinity towards Insulin‐regulated aminopeptidase. Further, the molecular docking study with Insulin‐regulated aminopeptidase receptor has shown the higher affinity of the titled compounds to the zinc binding pocket over the other pockets.

show abstract

Study of self-assembly features in 4H-pyrans: Synthesis, Hirshfeld surface, and energy framework analysis

Cited by 7 publications

References 37 publications

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

Non‐Covalent Interactions in the Self‐Assembly of Dihydropyridone Supramolecules and In Vitro Anti‐Cancer Assessment in Human Lung Adenocarcinoma Cell Line (A549)

Synthesis of Spirooxindoles and Study of their Self‐Assembly features; Hirshfeld Surface, Energy Framework andIn Silicoanalysis

Contact Info

Product

Resources

About