Chiroptical Properties of Acridino-18-Crown-6 Ligands and Their Complexes with Chiral and Achiral Protonated Primary (Aralkyl) Amine Guest Molecules

Szarvas, Szilvia; Májer, Zsuzsa; Huszthy, Péter; Vermes, Borbála; Hollósi, Miklós

doi:10.1080/10242430215699

Cited by 14 publications

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“…The unique CHEF effect, which was induced by Pi, can be attributed to the additional hydrogen bonding between the hydrogen of OH in the Pi and nitrogen on the acridine moiety . Similar hydrogen bonding between ammonium hydrogen and nitrogen acridine was reported by Hollósi et al Recently, the fluorescence enhancement due to the interaction between metal ions and a nitrogen on acridine was also reported …”

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confidence: 80%

Simple but Effective Way to Sense Pyrophosphate and Inorganic Phosphate by Fluorescence Changes

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Simple but Effective Way to Sense Pyrophosphate and Inorganic Phosphate by Fluorescence Changes

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“…3,5 The 1 B b band in the UV spectra of (R,R)-1a,b and (S,S)-1c near 270 nm and at 263 nm in that of (R,R)-2 appeared in the CD spectra varied. A doublet showed up in the spectra of (R,R)-1a,b, while a single positive 1 B b band of differing intensity was observed in the spectra of (S,S)-1c and (R,R)-2 ( Fig.…”

Section: Spectra Of the Crown Ether Hostsmentioning

confidence: 95%

“…From the sign of the exciton couplet the absolute conformation of the complexes could be deduced. 3,5 The structure of cation complexes of chiral crown ethers has been studied extensively by X-ray crystallography, NMR, IR, UV, and fluorescence spectroscopies, and microcalorimetry. 6 CD spectroscopy has also been used to examine the alkali and alkaline-earth complexes of selected pyridino crown ether hosts.…”

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Chiroptical properties of cation complexes of chiral phenazino‐18‐crown‐6 ether‐type hosts

Szarvas¹,

Szalay²,

Vass³

et al. 2005

Chirality

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Herein we report CD spectroscopic studies on complexes of (R,R)-dimethyl-, (R,R)-diisobutyl-, and (S,S)-di-sec-butyl-phenazino-18-crown-6 ligands (Scheme 1) with selected alkali (Na+, K+), alkaline earth (Mg2+, Ca2+), and transition-metal (Ag+, Zn2+, Ni2+, Cd2+, Pb2+) cations. The complexation was monitored in the 300- to 240-nm region of the CD spectra comprising mainly the 1Bb band of the heteroaromatic subunit. The CD spectra of the complexes showed an unexpected diversity. In the most characteristic 1Bb spectral region, the number, position, and intensity of band(s) depend not only on the heteroaromatic subunit and the size of the substituents but also on the diameter, ion strength, and coordination geometry of the cation. The appearance of two weak 1Bb CD bands (type-I spectra) with the sign pattern of the host is an indication of two complexes of comparable stability. The "type-II" spectra differ from that of the host in the number, sign pattern, and intensity of the bands. Complexes of transition-metal cations generally show CD spectra with more intense bands. The CD spectra of complexes of (S,S)-di-sec-butyl-phenazino-18-crown-6 ligand with Na+, K+, and Pb2+ (type III) strongly suggest exciton coupling caused by the closeness of the heteroaromatic rings of two 1:1 complex molecules.

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“…In the last few years our research in this area has been focused on the synthesis of enantiopure crown ethers containing heterocyclic (pyridine [16,18], [34]- [40], acridine [41]- [43] and phenazine [39,41], [44]- [48]) subunits and their enantiomeric recognition with chiral protonated primary aralkyl amines, amino acids and their derivatives.…”

Section: Chiral Crown Ethersmentioning

confidence: 99%

Synthesis and molecular recognition studies of crown ethers

Huszthy¹,

Tóth²

2007

Per. Pol. Chem. Eng.

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This short review summarizes the synthesis and molecular recognition studies of crown ether type macrocycles accomplished at the Institute for Organic Chemistry of Budapest University of Technology and Economics in the last few years. The research work reported here belongs to the areas of protonionizable crown ethers and chiral macrocycles.Proton-ionizable crown ethers at higher pH s than their pK a values are mostly ionized to ligand anions which increase the cation-ligand complex stability with enhancement of selectivity and avoid the need for a counter anion to accompany the cation transport or solvent extraction. The latter factor is not only advantageous from energetical point of view, but is also important when counter anions are not required to be transported.Enantiopure chiral macrocycles have also drawn the attention of many researchers, because owing to their enantioselective complexation they are excellent candidates for effective sensors and selectors of the enantiomers of biologically important chiral compounds such as protonated primary organic amines, amino acids and the derivatives of the latters. Keywords molecular recognition · enantiomeric recognition · protonionizable crown ethers · chiral crown ethers · chiral stationary phases Acknowledgement This work was supported by the Hungarian Scientific Research Fund (OTKA K62654) and by the Ministry of Education of Hungary (Postdoctoral Fellowship PAL 11/2003). Péter HuszthyDepartment of Organic Chemistry, BME, H-1111, Budapest, Szent Gellért tér 4., Hungary e-mail: huszthy@mail.bme.hu Tünde TóthDepartment of Organic Chemistry, BME, H-1111, Budapest, Szent Gellért tér 4., Hungary 1 Introduction Molecular recognition is a generally occurring phenomenon in nature. Examples include the storage and retrieval of genetic information by the DNA double helix, the selective binding of a subtrate by the active site of an enzyme, the antibodyantigen interactions, selective transport of metal ions by natural ionophores through different biomembranes and incorporation of the single enantiomeric forms of amino acids and sugars in metabolic pathways. The latter two examples refer to enantiomeric recognition. Enantiomeric recognition, as a special case of molecular recognition involves the discrimination between enantiomers of the guest by a chiral host. It was believed a few decades ago that molecular recognition was the result of unique properties of complex biomolecules. However, recent successes in imitating such phenomena using relatively simple synthetic compounds have demonstrated that biological behaviour can be engineered into small molecules. Crown ether type macrocycles for example offer unusual opportunities for the study of molecular recognition. These kinds of studies are not only important, because we can get deeper insight and understandig of molecular recognition in the living organisms, but also, because as a result of these studies we can develop new molecular sensors and selectors for practical applications.Probably the greatest impetus...

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Chiroptical Properties of Acridino-18-Crown-6 Ligands and Their Complexes with Chiral and Achiral Protonated Primary (Aralkyl) Amine Guest Molecules

Cited by 14 publications

References 0 publications

Simple but Effective Way to Sense Pyrophosphate and Inorganic Phosphate by Fluorescence Changes

Simple but Effective Way to Sense Pyrophosphate and Inorganic Phosphate by Fluorescence Changes

Chiroptical properties of cation complexes of chiral phenazino‐18‐crown‐6 ether‐type hosts

Synthesis and molecular recognition studies of crown ethers

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