Solid-state chemistry and structures of a new class of mixed dyes. Cyanine-oxonol

Etter, Margaret C.; Kress, Ruth B.; Bernstein, Joel; Cash, Derek J.

doi:10.1021/ja00335a009

Cited by 35 publications

(13 citation statements)

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“…Similar to the inclusion in crystals of hydroxylic solvents (e.g., water and alcohols), which is favored by the HBs the solvents form with HB acceptor sites in the crystallized molecule, the inclusion and tight binding of halogenated solvents is favored whenever XB acceptor sites are present in the crystal components. Many solvates wherein CHCl 3 and CH 2 Cl 2 − or, less frequently, CCl 4 and CCl 2 CCl 2 , are halogen-bonded to a variety of anions have been obtained serendipitously. The same holds for solvated systems wherein a lone-pair-possessing XB donor pins the halocarbon.…”

Section: Nature Of the Halogen Bondmentioning

confidence: 87%

The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Nature Of the Halogen Bondmentioning

confidence: 87%

The Halogen Bond

et al. 2016

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“…For the remarkable cyanine/oxonol system (9/ 10) at least fourteen different polymorphs or solvates have been identified. [72] Two of these, a gold and a red form (each containing a molecule of CHCl 3 solvent per 1:1 complex, and hence true polymorphs) crystallize concomitantly and have been structurally characterized. [72] Three of these polymorphs are shown in Figure 11.…”

Section: Concomitant Crystallization Of Multicomponent Systemsmentioning

confidence: 99%

“…[72] Two of these, a gold and a red form (each containing a molecule of CHCl 3 solvent per 1:1 complex, and hence true polymorphs) crystallize concomitantly and have been structurally characterized. [72] Three of these polymorphs are shown in Figure 11. Despite the fact that both of these dyes are known to be individually self-aggregating, [73] the two Figure 11.…”

Section: Concomitant Crystallization Of Multicomponent Systemsmentioning

confidence: 99%

Concomitant Polymorphs

Bernstein

Davey

Henck

1999

Angewandte Chemie Intl Edit

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817

671

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The simultaneous appearance of polymorphs of a substance has long been recognized but rarely noted or systematically studied. This phenomenon can be useful in the investigation of solid materials and in understanding the relative crystal energetics of polymorphic materials. This review covers the thermodynamic and kinetic factors that govern competitive and concomitant polymorphic crystallization. One of the many examples surveyed is a cyanine/oxonol complex, for which different relative molecular orientations in two of the many reported polymorphs are shown.

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“…3-Ethyl-2-methylbenzothiazolium iodide, 1a, was used for the preparation of the perchlorate, 1b. The formyl derivative of phenylaza-15-crown-5, 2b, was prepared according to the literature, 21 and the condensation of 1b with 2b was carried out in absolute ethanol in the presence of pyridine as a catalyst.…”

Section: Synthesismentioning

confidence: 99%

Structure and ion-complexing properties of an aza-15-crown-5 ether dye: synthesis, crystallography, NMR spectroscopy, spectrophotometry and potentiometry

Алфимов¹,

Churakov²,

Fedorov³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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The perchlorate of 2-{2-[4-(13-aza-1,4,7,10-tetroxa-13-cyclopentadecyl)phenyl]ethenyl}-3-ethylbenzothiazolium (3) has been synthesised and its structure determined in the crystalline state by X-ray diffraction and in solution in acetonitrile by 1 H NMR methods. Complexation with barium and silver cations in solution has been studied in comparison with other model azacrown molecules by spectrophotometric and potentiometric methods. With the exception of the puckered azacrown moiety, the structure of 3 is remarkably planar, consistent with extensive -conjugation throughout the remainder of the molecule in both solid and solution states. Compound 3 forms a stable 1 : 1 complex with Ba 2ϩ ions in acetonitrile, with a stability constant of K 1 = 80 ± 10 dm 3 mol Ϫ1 ; the complexation results in major changes in the electronic absorption spectrum of 3, consistent with binding to the azacrown moiety. A model compound, phenylaza-15-crown-5 (2a), was found to bind Ba 2ϩ to form both a 1 : 1 ligand-metal complex (LM), with a stability constant of K 1 = (2.0 ± 0.2) × 10 4 dm 3 mol Ϫ1 , and a 2 : 1 (L 2 M) complex, with a stability constant of K 2 = 220 ± 20 dm 3 mol Ϫ1 for binding of the second ligand. The electronic absorption and NMR spectra both indicate binding of the 'hard' Ba 2ϩ cation to the azacrown oxygen atoms. However, by contrast, the evidence from NMR data shows that the 'soft' Ag ϩ cation complexes with 2a mainly through a strong interaction with the azacrown nitrogen atom, giving a 1 : 1 complex with a stability constant of K 1 = 6 ± 1 dm 3 mol Ϫ1 , determined by potentiometry. No complexation of 3 with Ag ϩ is observed. Studies of the simple aza-15-crown-5 ether reveal strong complexation with both Ba 2ϩ (K 1 × K 2 > 10 12 dm 6 mol Ϫ2 ) and Ag ϩ [K 1 = (1.15 ± 0.10) × 10 4 dm 3 mol Ϫ1 and K 2 = 450 ± 20 dm 3 mol Ϫ1 ].

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Solid-state chemistry and structures of a new class of mixed dyes. Cyanine-oxonol

Cited by 35 publications

References 0 publications

The Halogen Bond

The Halogen Bond

Concomitant Polymorphs

Structure and ion-complexing properties of an aza-15-crown-5 ether dye: synthesis, crystallography, NMR spectroscopy, spectrophotometry and potentiometry

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