Fluorescence improvement of pyridylacrylonitrile by dimethylaminophenyl-substitutions: The effect of packing modes of conjugated compounds

Percino, M. Judith; Chapela, Víctor M.; Cerón, Margarita; Soriano‐Moro, Guillermo; Castro, María Eugenia; Meléndez, Francisco J.

doi:10.1016/j.molstruc.2012.10.025

Cited by 18 publications

(25 citation statements)

References 42 publications

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“…Table lists the selected bond lengths and torsion angles for the structures of I and II . The results support the idea that the p ‐dimethylaminophenyl moiety, the ring formed by atoms C(10)–C(11)–C(12–C(13)–C(14)–C(15) in I and C(3)–C(4)–C(5)–C(6)–C(7)–C(8) in II behaves as a quinoid structure, which is typically found for compounds with this functional group …”

Section: Resultsmentioning

confidence: 60%

“…The one photon absorption spectra in the UV spectra of each pair of crystals (yellow and orange) dissolved in CHCl 3 or in CH 2 Cl 2 showed two absorption bands: one at λ max 296–301 nm, corresponding to the n→π* transition due to electron transfer from the amine moieties and a second absorption band with λ max at 416–427 nm, which is assigned to π–π* transition of the conjugated double bond . The presence of the substituents, either the N(CH 3 ) 2 or ‐N(Ph) 2 group, increased the intensity of the bands assigned to n→π*, which corresponded to the extended delocalization of the nitrogen pair onto the additional two phenyl groups from ‐N(Ph) 2 than ‐N(CH 3 ) 2 , that transferred to the whole molecule …”

Section: Resultsmentioning

confidence: 99%

“…These compounds differ in the emission in the solid state as compared with the emission from the solution. Our goal was to comprehend the cause of the differences in emission for Z‐2‐(4‐bromophenyl)‐3‐(4‐dimethylaminophenyl)acrylonitrile in solid state and in solution . We describe the study of five compounds ( I–V , see Scheme ) selected according to dyes families to compare plane‐to‐plane stacking versus to face‐to‐edge.…”

Section: Introductionmentioning

confidence: 93%

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Preferential Orientation of Crystals and its Influence on the Emission Wavelength of Acrylonitrile Derivatives Treated with Polar Solvents

Percino

Cerón

Pérez–Gutiérrez

et al. 2019

Crystal Research and Technology

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Photoluminescence properties in solid state and its relationship with structural features of prop-2-enenitrile derivatives containing any of functional groups 4-halogenphenyl, phenyl, 4-dimethylamino, or 4-diphenylamino are investigated. The compounds show change in color from yellow to orange after treatment with dimethyl sulfoxide or dimethyl formamide. Nevertheless, the single-crystal X-ray diffraction for both, the original yellow and the treated orange crystals, does not display any major structural differences. The optical properties are related to the crystal packing and intermolecular interactions such as edge-to-face through the vertices of aromatic rings. The last is supported by the behavior of the presence of functional group. The absorption spectrum in solution for all compounds shows two absorption bands with wavelength of maximum absorption around 390-430 nm and at 290-300 nm. Regardless of the crystal type, the maximum emission in solution was between 450-570 nm. In solid state, yellow crystals exhibit an emission in the 500-530 nm range and in the 580-630 nm range for orange crystals. Results suggest that optical properties are strongly dependent on morphology and habit. Powder X-ray characterization shows a preferential orientation for orange crystals. All compounds are characterized by common spectroscopy techniques, fluorescence, atomic force microscopy and X-ray diffraction.

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Section: Resultsmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 93%

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Preferential Orientation of Crystals and its Influence on the Emission Wavelength of Acrylonitrile Derivatives Treated with Polar Solvents

Percino

Cerón

Pérez–Gutiérrez

et al. 2019

Crystal Research and Technology

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“…The intermolecular hydrogen bonds are similar than other systems presenting NÁÁÁH-O interactions between the stacked molecules [21]. It has been demonstrated these hydrogen bonds play an important role in the symmetry of the unit cell and the packing modes in conjugated compounds [21,22].…”

Section: Resultsmentioning

confidence: 70%

Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde

et al. 2013

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The 1-phenyl-2-(a-pyridyl)ethanol [or 1-phenyl-2-(2-pyridyl)ethanol] compound was obtained from the Knoevenagel condensation reaction between 2-methylpyridine with benzaldehyde without catalyst or solvent. The compound was characterized by IR, 1 H-NMR, and by single crystal X-ray diffraction. The X-ray structure clearly revealed that the compound crystallizes in a monoclinic system with centrosymmetric space group, P2 1 /c, with Z 0 = 1. The unit cell dimensions are a = 5.2481 (3), b = 8.2862(4), c = 23.8498(14) Å , and b = 96.761(5)°. The crystal structure showed the formation of one intermolecular hydrogen bond O-HÁÁÁN between the oxygen atom of the O-H and the nitrogen atom of the pyridine group of the adjacent molecule. The crystallography data gave evidence that the intermediate compound is a new stable 1-phenyl-2-(2-pyridyl)ethanol intermediate which presents an interesting relationship between stability and hydrogen bonds formation in the structure for obtaining similar compounds that have been proposed in the literature.Also, it is shown that it is just before the dehydration process which yields the trans double bond of the 1-phenyl-2-(2-pyridyl)ethene.

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“…For comparison, the solid‐state emission of 1‐3 was measured and the emission wavelength follows the order 1 (507 nm) < 2 (524 nm) < 3 (564 nm) (Figure S4 and Table S4). Tight molecular packing in solid‐state disallows suppression of vibrational relaxation modes responsible for fast excited‐state deactivation and resulting in emission intensity enhancement . Morphological studies of the molecules in water using scanning electron microscopy reveal irregular aggregates for all the stilbenes with a slightly greater order for stilbene 3 (Figure S5).…”

Section: Resultsmentioning

confidence: 99%

One‐ and Two‐Component Organogels Containing Cyanostilbene without any Auxiliary Substituents

et al. 2019

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Pyridyl acrylonitrile without traditional auxiliary groups form stable organogels in ethanol. The addition of a second non‐gelating cyanostilbene component results in a more stable two‐component gel. Single crystal X‐ray data reveal the influence of C−H⋅ ⋅ ⋅N, C−H⋅ ⋅ ⋅π, and π–π interactions in the formation of organogels. The morphology of the xerogels was studied by using SEM, which showed the self‐assembly of molecules to fibers and sheet‐like structures, and phase differences upon the gel formation and the structural phase characterization was measured using powder XRD. Exposure of the organogels to acidic (TFA) vapors results in distinct color changes and loss of gelation properties, thus highlighting the potential of these gels in sensing. The results represent a rare example of two‐component organogels using two different cyanostilbene units and show that functional two‐component organogels can be formed by utilizing the synergistic effects of the individual components.

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Fluorescence improvement of pyridylacrylonitrile by dimethylaminophenyl-substitutions: The effect of packing modes of conjugated compounds

Cited by 18 publications

References 42 publications

Preferential Orientation of Crystals and its Influence on the Emission Wavelength of Acrylonitrile Derivatives Treated with Polar Solvents

Preferential Orientation of Crystals and its Influence on the Emission Wavelength of Acrylonitrile Derivatives Treated with Polar Solvents

Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde

One‐ and Two‐Component Organogels Containing Cyanostilbene without any Auxiliary Substituents

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