Synthesis of Three Stereoisomers of p-tert-Butylthiacalix[4]arene Substituted with (Ethoxycarbonyl)methoxy and Fluorescent 1-Amidoanthraquinone Fragments

Vavilova, Alena A.; Nosov, Roman; Mostovaya, O. A.; Stoikov, Ivan I.

doi:10.6060/mhc160531s

Cited by 11 publications

(7 citation statements)

References 20 publications

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“…There is no effect of the conformation on the position of the emission maxima and on the shape of the spectra of the studied compounds, which is characteristic for thiacalixarene derivatives [ 52 – 53 ]. This is probably due to the fact that the substituents are long and removed from the macrocyclic fragment, and the shielding of tert-butyl groups by fluorophores is not observed.…”

Section: Resultsmentioning

confidence: 99%

Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

Padnya

Khripunova

Mostovaya

et al. 2017

Beilstein J. Nanotechnol.

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New water-soluble tetra-substituted derivatives of p-tert-butylthiacalix[4]arene containing fragments of L-tryptophan in cone and 1,3-alternate conformations were obtained. It was shown that the resulting compounds form stable, positively charged aggregates of 86–134 nm in diameter in water at a concentration of 1 × 10−4 M as confirmed by dynamic light scattering, scanning electron microscopy and transmission electron microscopy. It was established that these aggregates are fluorescently active and chiral. A distinctive feature of the compounds is the pronounced dependence of their spectral (emission and chiroptical) properties on the polarity of the solvent and the length of the linker between the macrocyclic and fluorophore parts of the molecule.

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Section: Resultsmentioning

confidence: 99%

Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

Padnya

Khripunova

Mostovaya

et al. 2017

Beilstein J. Nanotechnol.

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“…The residue was crystallized from ethanol as light-yellow powder. 4,8,14,18,23,26,28,31,32,) methoxy]-pillar [5]arene (8) 7.42 (10H, s, Ar-H). 13 6.86 (10Н, s, Ar-H).…”

Section: Synthesesmentioning

confidence: 99%

“…[1][2][3][4][5][6] As a rule, a key role in these processes is played by macrocyclic compounds. [7][8][9][10][11][12][13] Depending on the size of the cavity, they are able to form host-guest systems, [14][15][16] leading to the formation of various supramolecular assembles.…”

Section: Introductionmentioning

confidence: 99%

Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

Shurpik¹,

Yakimova²,

Stoikov³

et al. 2017

MHC

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Pillar[5]arenes bearing amide and carboxylic groups have demonstrated recognition performance for some representative alkali metal ions including Li + , Na + , K + and Cs + in series cations of sand d-metals compared to pillar[5] arenes with hydroxyl, methoxy and acetone fragments. Their complexation abilities toward these cations were evaluated by UV-Vis technique. The complexation results revealed that pillar[5]arene, containing glicylglicyne groups, were the most efficient cation receptors for Li + , Na + , K + and Cs + over other synthesized and studied pillar[5]arenes. Introduction of long glycylglycide fragments into macrocycle structure allowed to increase the association constant logarithm in the case of Li + by 2 orders. In addition, in the set of macrocycles, incorporation of the additional amide fragments and carboxyl group into macrocycle structure leads to increasing the binding efficiency with alkali metal cations.

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“…The conformation of p-tert-butylthiacalix [4]arene derivatives is usually determined by using the twodimensional NMR spectroscopy techniques. [39][40][41][42][43] However, in one-dimensional 1 H NMR spectra, the compounds 49 obtained can be distinguished by characteristic signals of the protons, which can clearly establish the conformation of the macrocycle. The conformational correlation of cone 4 and 7 stereoisomers, and 1,3-alternates 6 and 9 tetrasubstituted at the lower rim of p-tert-butylthiacalix [4] arene can be realized by comparison of the chemical shifts of protons of OCH 2 C(O) groups in the 1 H NMR spectra.…”

Section: Synthesismentioning

confidence: 99%

Iminodiacetic Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis and Influence of Conformation on the Aggregation with Bismarck Brown Y

Shurpik¹,

Stoikov²,

Osin³

et al. 2017

MHC

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Three conformers (cone, partial cone and 1,3-alternate) of tetrasubstituted at the lower rim p-tert-butylthiacalix[4] arene derivatives with iminodiacetic fragments were synthesized and characterized. It was shown by spectral methods (UV-Vis, 1 H NMR and DOSY spectroscopy, DLS) and TEM that the monodisperse nano-sized particles are formed by self-assembly of synthetic octaacids in water with azo dye Bismarck brown Y in the case of the partial cone and 1,3-alternate conformations. It was found that the dye associates with the acid binding sites of the macrocycle.

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Synthesis of Three Stereoisomers of p-tert-Butylthiacalix[4]arene Substituted with (Ethoxycarbonyl)methoxy and Fluorescent 1-Amidoanthraquinone Fragments

Cited by 11 publications

References 20 publications

Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

Iminodiacetic Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis and Influence of Conformation on the Aggregation with Bismarck Brown Y

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