The selective preparation of partial cone O-aryl calix[4]arene ethers from 1,3-dimethoxycalix[4]arene: a new platform for the preparation of non-aggregated dyes

O'Malley, Shane; Alhashimy, Nameer; O’Mahony, John; Kieran, Aisling; Pryce, Mary T.; Nolan, Kieran

doi:10.1016/j.tetlet.2006.11.095

Cited by 7 publications

(5 citation statements)

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“…With a long-term goal of developing new calix-based dyes, the Nolan group developed phthalocyanine derivative 182 (Figure ) in the partial cone conformation . NMR analysis showed that this dye had a reduced propensity to aggregate, while fluorescence studies (excitation at 650 nm) resulted in strong fluorescence at 715 nm with a Stokes shift of 7 nm relative to phthalocyanine itself.…”

Section: Calix[4]arene-based Receptorsmentioning

confidence: 99%

“…With a long-term goal of developing new calix-based dyes, the Nolan group developed phthalocyanine derivative 182 (Figure 38) in the partial cone conformation. 319 NMR analysis showed that this dye had a reduced propensity to aggregate, while fluorescence studies (excitation at 650 nm) resulted in strong fluorescence at 715 nm with a Stokes shift of 7 nm relative to phthalocyanine itself. Similarly, excitation at 614 nm resulted in the same fluorescence spectrum as that of phthalocyanine, indicating that the phthalocyanine group in 182 was unaffected by the calix moiety.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

et al. 2019

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Calix[n]arenes (n = 4, 5, 6, 8) are "chalicelike" phenol-based macrocycles that are among the most fascinating and highly studied scaffolds in supramolecular chemistry. This stems from the functional and tunable diversity at both their upper and lower rims, their preorganized nonpolar cavities and preorganized ionbinding sites, and their well-defined conformations. Conjugation of calixarene scaffolds with various fluorogenic groups has led to the development of smart fluorescent probes that have been utilized as molecular sensors, in bioimaging, for drug and gene delivery, in self-assembly/aggregation, and as smart materials. The fine-tuning and incorporation of different ligating sites in the calix[4]arene scaffold have produced numerous molecular sensors for cations, anions, and biomolecules. Moreover, the aqueous solubility of p-sulfonatocalix[4]arenes has engendered their potential use in drug/gene delivery and enzymatic assays. In addition, because of their strong optical properties, fluorescent calix[4]arenes have been used to develop smart materials, including gels as well as nonlinear optical, organic light-emitting diode, and multiphoton materials. Finally, significant developments in the utility of fluorescent higher calixarenes have been made for bioapplications. This review critically summarizes the recent advances made in all of these different areas.

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Section: Calix[4]arene-based Receptorsmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

et al. 2019

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“…The separation of AABB and ABAB structures is inherently problematic, however, since these isomers have identical molecular weights and usually have similar molecular properties. There are some examples of the complete resolution and characterization of the four products for both peripheral substitution 87,192,195,[197][198][199][200] and fused ring modification, 93,181,182,184,[187][188][189][190][191]201 but most recent low symmetry Pc studies have focused on the relatively easily separated AAAB products formed through partial peripheral substitution of Pz, 100,[202][203][204][205][206][207][208][209][210][211][212] Nc, 213 unsubstituted Pc, [213][214][215][216][217][218][219][220][221][222][223][224][225][226][227][228]…”

Section: Mixed and Cross-condensationsmentioning

confidence: 99%

“…The separation of AABB and ABAB structures is inherently problematic, however, since these isomers have identical molecular weights and usually have similar molecular properties. There are some examples of the complete resolution and characterization of the four products for both peripheral substitution ,,,− and fused ring modification, ,,,,− , but most recent low symmetry Pc studies have focused on the relatively easily separated AAAB products formed through partial peripheral substitution of Pz, ,− Nc, unsubstituted Pc, − α-substituted Pc, ,− β-substituted tetrapyrazoporphyrazine, β-substituted P c, − ,− ,− ,,,,− ,− …”

Section: Peripheral Substitution and Fused Ring Modificationmentioning

confidence: 99%

“…There has been a growing focus on excited state properties over the past decade . Fluorescence excitation and emission spectra, ,,,,− ,,,,,,,,− ,,,,,,, ,,,,,,,,,− ,,,,,,,,,,,,,,,,,,,,,,,,,,,, excited state lifetimes and decay curves, ,,,,,,,,,,,,,,,,,,,,,,− ,,,,,,,,,,, fluorescence quantum yields, ,,,…”

Section: Peripheral Substitution and Fused Ring Modificationmentioning

confidence: 99%

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Low Symmetry Phthalocyanines and Their Analogues

2010

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Clathrate Formation from Octaazaphthalocyanines Possessing Bulky Phenoxyl Substituents: A New Cubic Crystal Containing Solvent‐Filled, Nanoscale Voids

Makhseed

Ibrahim

Samuel

et al. 2008

Chemistry A European J

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The synthesis of octaazaphthalocyanine (AzaPc) derivatives, with bulky phenoxyl substituents placed at eight peripheral positions and containing either H(+), Ni(2+) or Zn(2+) ions in their central cavity, is described. The required precursors, derivatives of pyrazine-2,3-dicarbonitrile, were prepared using a nucleophilic aromatic substitution reaction between 2,6-diisopropylphenol or 2,6-diphenylphenol and 5,6-dichloropyrazine-2,3-dicarbonitrile. Analysis of the resulting AzaPcs by UV/Visible and (1)H NMR spectroscopy confirms that steric isolation of the AzaPc cores was enforced both in solution and in the solid state. X-ray diffraction studies of single crystals of the AzaPcs reveal that solvent inclusion takes place in each case. Of particular significance is the finding that the zinc derivative of 2,3,9,10,16,17,23,24-octa-(2,6-diisopropylphenoxy)octaazaphthalocyanine provides nanoporous cubic crystals, containing massive (8 nm(3)) solvent-filled voids, similar to those of the analogous phthalocyanine derivative. Exchange of the included solvent within the voids can be readily achieved by using a number of alternative solvents including water. Based on the observed loading of included water, the internal volume of this nanoporous cubic crystal appears to be more hydrophilic than its phthalocyanine counterpart.

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The selective preparation of partial cone O-aryl calix[4]arene ethers from 1,3-dimethoxycalix[4]arene: a new platform for the preparation of non-aggregated dyes

Cited by 7 publications

References 10 publications

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

Low Symmetry Phthalocyanines and Their Analogues

Clathrate Formation from Octaazaphthalocyanines Possessing Bulky Phenoxyl Substituents: A New Cubic Crystal Containing Solvent‐Filled, Nanoscale Voids

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