Synthesis and comparative structural study of 2-(pyridin-2-yl)-1<i>H</i>-perimidine and its mono- and di-<i>N</i>-methylated analogues

Kalle, Paulina; Tatarin, Sergei V.; Zakharov, A. Yu.; Kiseleva, Marina A.; Bezzubov, Stanislav I.

doi:10.1107/s205698902100013x

Cited by 3 publications

(1 citation statement)

References 11 publications

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“…2-(2-Thienyl)-perimidine L1 was prepared in high yield via condensation of 1,8-diaminonaphthalene with 2-thiophenecarboxaldehyde in the presence of sodium metabisulfite ( Scheme 1 ) [ 25 , 26 ]. N -methylation of L1 was conducted with methyl iodide in alkaline media under inert atmosphere to prevent oxidation of the perimidine system (73% yield).…”

Section: Resultsmentioning

confidence: 99%

A Panchromatic Cyclometalated Iridium Dye Based on 2-Thienyl-Perimidine

et al. 2022

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Though 2-arylperimidines have never been used in iridium(III) chemistry, the present study on structural, electronic and optical properties of N-unsubstituted and N-methylated 2-(2-thienyl)perimidines, supported by DFT/TDDFT calculations, has shown that these ligands are promising candidates for construction of light-harvesting iridium(III) complexes. In contrast to N-H perimidine, the N-methylated ligand gave the expected cyclometalated μ-chloro-bridged iridium(III) dimer which was readily converted to a cationic heteroleptic complex with 4,4′-dicarboxy-2,2′-bipyridine. The resulting iridium(III) dye exhibited panchromatic absorption up to 1000 nm and was tested in a dye-sensitized solar cell.

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Section: Resultsmentioning

confidence: 99%

A Panchromatic Cyclometalated Iridium Dye Based on 2-Thienyl-Perimidine

et al. 2022

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Synthesis, X-ray structures, Hirshfeld surface analysis, and redox behaviour of 2-substituted-1H-perimidine derivatives

Angarkhe,

Shaikh,

Rout

et al. 2024

Journal of Molecular Structure

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Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine

et al. 2022

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The title compounds, 2-(4-methylphenyl)-1H-perimidine hemihydrate (1, C18H14N2·0.5H2O) and 1-methyl-2-(4-methylphenyl)-1H-perimidine (2, C19H16N2), were prepared and characterized by 1H NMR and single-crystal X-ray diffraction. The organic molecule of the hemihydrate lies on a twofold rotation axis while the water molecule lies on the intersection of three twofold rotation axes (point group symmetry 222). As a consequence, the hydrogen atoms that are part of the N—H group and the water molecule as well as the CH3 group of the p-tolyl ring are disordered over two positions. In compound 1, the perimidine and the 2-aryl rings are slightly twisted while its N-methylated derivative 2 has a more distorted conformation because of the steric repulsion between the N-methyl group and the 2-aryl ring. In the crystal structures, molecules of perimidine 2 are held together only by C—H...π contacts while the parent perimidine 1 does not exhibit this type of interaction. Its crystal packing is established by intermolecular N—H...O hydrogen bonds with the solvent water molecules and additionally stabilized by π–π stacking.

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Synthesis and comparative structural study of 2-(pyridin-2-yl)-1H-perimidine and its mono- and di-N-methylated analogues

Cited by 3 publications

References 11 publications

A Panchromatic Cyclometalated Iridium Dye Based on 2-Thienyl-Perimidine

A Panchromatic Cyclometalated Iridium Dye Based on 2-Thienyl-Perimidine

Synthesis, X-ray structures, Hirshfeld surface analysis, and redox behaviour of 2-substituted-1H-perimidine derivatives

Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine

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