Synthesis and optical properties of linear and branched styrylpyridinium dyes in different environments

Gordel-Wójcik, Marta; Nyk, Marcin; Bajorek, Agnieszka; Zych, Eugeniusz; Samoć, Marek; Jędrzejewska, Beata

doi:10.1016/j.molliq.2022.119007

Cited by 7 publications

(3 citation statements)

References 64 publications

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“…On the other hand, the Knoevenagel reaction ( Gordel-Wojcik et al, 2022 ) is one of the most famous carbon-carbon coupling process to synthesize α,β-unsaturated compounds. In recent years, the synthesis of the Knoevenagel products in the presence of heterogeneous and homogeneous catalysts has been investigated under different conditions.…”

Section: Introductionmentioning

confidence: 99%

Amine-containing yolk-shell structured magnetic organosilica nanocomposite as a highly efficient catalyst for the Knoevenagel reaction

Neysi,

Elhamifar

2024

Front. Chem.

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The yolk-shell structured silica nanocomposites have been considered by many researchers due to their specific physical and chemical properties. These materials have been widely used in adsorption and catalysis processes. Especially, the void space of yolk−shell nanostructures can provide a unique environment for storage, compartmentation, and confinement in host−guest interactions. In this paper, for the first time, the preparation, characterization, and catalytic application of a novel amine-containing magnetic methylene-based periodic mesoporous organosilica with yolk-shell structure (YS-MPMO/pr-NH2) are developed. The magnetic periodic mesoporous organosilica nanocomposite was synthesized through surfactant-directed co-condensation of bis(triethoxysilyl)methane (BTEM) and tetraethoxysilane around Fe3O4 nanoparticles. After Soxhlet extraction, the surface of YS-MPMO nanocomposite was modified with 3-aminopropyl trimethoxysilane to deliver YS-MPMO-pr-NH2 nanocatalyst. This catalyst was characterized by using EDX, FT-IR, VSM, TGA, XRD, nitrogen-sorption, and SEM analyses. The catalytic activity of YS-MPMO/pr-NH2 was studied in the Knoevenagel reaction giving the corresponding products in a high yield and selectivity. The YS-MPMO/pr-NH2 nanocatalyst was recovered and reused at least four times without a significant decrease in efficiency and activity. A leaching test was performed to study the nature of the catalyst during reaction conditions Also, the catalytic performance of our designed nanocomposite was compared with some of the previous catalysts used in the Knoevenagel reaction.

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Section: Introductionmentioning

confidence: 99%

Amine-containing yolk-shell structured magnetic organosilica nanocomposite as a highly efficient catalyst for the Knoevenagel reaction

Neysi,

Elhamifar

2024

Front. Chem.

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Section: Introductionmentioning

confidence: 99%

“…Styrylpyridinium compounds were used in a range of biological applications as fluorescent dyes [10][11][12][13]. The development of novel derivatives of fluorescent dyes using such motifs as building blocks remains a priority area [12,13]. Recently naphthylvinyl-pyridinium dyes were proposed as structurally compact, blue−green−red fluorescence trackers which selectively localized on the outer cell membrane [14].…”

Section: Introductionmentioning

confidence: 99%

1,1′-{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide

Ruciņš

Kaukulis

Plotniece

et al. 2022

Molbank

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Synthesis of a double-charged cationic amphiphilic 1,4-dihydropyridine derivative with dodecyl ester groups at positions 3 and 5 of the 1,4-DHP ring was performed starting from Hantzsch type cyclization of dodecyl acetoacetate, 2-naphthaldehyde and ammonium acetate. Bromination of this compound followed by nucleophilic substitution of bromine with (E)-4-(2-(naphthalen-2-yl)vinyl)pyridine gave the desired cationic amphiphilic 1,1′-{[3,5-bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide. The obtained target compound was fully characterized by IR, UV, 1H-NMR, 13C-NMR, HRMS and microanalysis. The characterization of the cationic 1,4-DHP nanoparticles in an aqueous solution was performed by DLS measurements. The obtained results showed that the compound formed nanoparticles with an average diameter of around 300 nm, a PDI value of around 490 and a zeta-potential of around 20 mV for freshly prepared samples. However, after one week of storage at room temperature, an aggregation of nanoparticles was detected.

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Organohalogenochromism: Toward Colorimetric Detection of Volatile Organic Halogen Compounds

Kozuka,

Imato,

Ooyama

2024

ChemPhotoChem

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A significant hypsochromic or bathochromic shift of photoabsorption bands of dyes may be observed only in halogenated solvents. Such specific solvatochromism is termed organohalogenochromism (OHC), which has been recently recognized as a photophysical phenomenon. However, few studies have been carried out on the elucidation of OHC and thus there is a limited insight into the mechanism for expression of OHC, although the phenomenon not only is of a great scientific interest in photochemistry, photophysics, analytical chemistry, and synthetic organic chemistry but also has great potential for development of colorimetric detection technique for organohalogen compounds; this technique is expected to be facile operation and simple analysis with sufficient accuracy, high sensitivity, and fast response, and thus allows visualization and real‐time monitoring for toxic volatile organohalogen compounds (VOHCs). In this Concept, we first review OHC of dyes which have been reported so far. Second, the elucidation of OHC based on the interactions between dye and organohalogen molecules are discussed. In particular, we propose the explanation for a pronounced OHC of donor‐π‐acceptor‐type cationic dye from the viewpoint of halogen bond (XB) between halogenated solvents and counter anion of cationic dye. Moreover, an application of organohalogenochromic dyes to colorimetric sensors for VOHCs is presented.

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Synthesis and optical properties of linear and branched styrylpyridinium dyes in different environments

Cited by 7 publications

References 64 publications

Amine-containing yolk-shell structured magnetic organosilica nanocomposite as a highly efficient catalyst for the Knoevenagel reaction

Amine-containing yolk-shell structured magnetic organosilica nanocomposite as a highly efficient catalyst for the Knoevenagel reaction

1,1′-{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide

Organohalogenochromism: Toward Colorimetric Detection of Volatile Organic Halogen Compounds

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