Synthesis of multicomponent crystals composed of 4-amino-1-methylpyridinium <i>p</i>-toluenesulfonate and phenol derivatives

Uno, Kazuyuki; Yamakado, Ryohei; Okada, Shuji

doi:10.1080/15421406.2022.2047348

Cited by 2 publications

(2 citation statements)

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“…[42,43] When hydrogen-bond donors such as phenol and benzoic acid derivatives were combined with 4-aminopyridinium p-toluenesulfonate, a few cocrystals containing three π-components were obtained. [44] In these cases, the hydrogen bonds were formed not only between the anion and the hydrogen-bond donor but also between the anion and the cation. Therefore, in this study, in order to promote introduction of the hydrogen-bond donor molecules as the third component in cocrystals, cations without hydrogenbond donor groups, such as 4-methyl-, 4-(dimethylamino)-, and 4-cyano-substituted 1-methylpyridiniums and 1-methylquinoliniums, were selected.…”

Section: Introductionmentioning

confidence: 99%

“…In previous studies, 1‐methylpyridinium benzenesulfonates were studied as second‐order nonlinear optical materials with short cutoff wavelengths [41] and, when cations were 4‐amino‐ or 4‐carbamoyl‐1‐methylpyridinium, hydrogen bonds between the hydrogen‐bond donor groups of the cations and sulfonates of the anions were found to effectively form polar orientation of the π‐conjugation systems [42,43] . When hydrogen‐bond donors such as phenol and benzoic acid derivatives were combined with 4‐aminopyridinium p ‐toluenesulfonate, a few cocrystals containing three π‐components were obtained [44] . In these cases, the hydrogen bonds were formed not only between the anion and the hydrogen‐bond donor but also between the anion and the cation.…”

Section: Introductionmentioning

confidence: 99%

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Preparation and Structures of Multicomponent Crystals Composed of Heteroaromatic Cations, p‐Toluenesulfonate Anion, and Aromatic Hydrogen‐Bond Donors

Uno,

Yamakado,

Okada

et al. 2024

Asian J Org Chem

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Cocrystals with three π‐components, which were a π‐cation, a π‐anion acting as a hydrogen‐bonding acceptor, and a π‐molecule acting as a hydrogen‐bonding donor, were prepared by the solution‐growth methods. The first and second components were ion pairs of 1‐methylpyridinium or 1‐methylquinolinium p‐toluenesulfonate derivatives, and the third components were dihydric phenol derivatives, like hydroquinone, 1,4‐naphthalenediol, 4,4’‐biphenol, and 1,1’‐bi‐2‐naphthol, or benzoic acid derivatives with hydroxy or amino group at the para position. Among 23 cocrystals found from 35 possible combinations of five ion‐pairs and seven hydrogen‐bonding donors, 20 cocrystals were investigated by the X‐ray crystallographic analyses. Some of them also contained solvent molecules. In these cocrystals, hydrogen‐bonding sequences composed of p‐toluenesulfonate and the hydrogen‐bonding donors were observed, and ionic bonds between the first and second components and hydrogen bonds between the second and third components were found to be responsible for three‐π‐component cocrystals. When the cations were 4‐cyanopyridinium or quinolinium derivatives, the cocrystals showed charge‐transfer absorption bands due to electronic interaction between the cations and the hydrogen‐bonding donors. To the mixture of quinolinium p‐toluenesulfonate and 1,1’‐bi‐2‐naphthol forming the three‐π‐component cocrystals, tetrathiafulvalene were added to form four‐π‐component cocrystals with ethanol or water molecules.

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Section: Introductionmentioning

confidence: 99%