Enantiomerically pure chiral phenazino-crown ethers: synthesis, preliminary circular dichroism spectroscopic studies and complexes with the enantiomers of 1-arethyl ammonium salts

Samu, Erika; Huszthy, Péter; Somogyi, László; Hollósi, Miklós

doi:10.1016/s0957-4166(99)00287-6

Cited by 38 publications

(39 citation statements)

References 25 publications

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“…This molecule was synthesized by Huszthy and co-workers 3 and its CD spectrum was recorded. 4 The characteristic features of the experimental CD spectrum (Fig.…”

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confidence: 99%

Theoretical CD spectrum calculations of the crown‐ether aralkyl‐ammonium salt complex

et al. 2002

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Rotatory strengths of the alpha-(1-naphtyl)-ethylammonium perchlorate (NEA)-phenazino-18-crown-6 ether molecular complex is determined theoretically by the coupled oscillator model and using ab initio random phase approximation (RPA) to describe local excitations on the chromophores. The computational results are compared to the experimental circular dichroism (CD) spectrum published previously. The good qualitative agreement between calculated and measured optical rotatory strengths allows one to assign the CD bands of the complex in a unique manner.

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“…This molecule was synthesized by Huszthy and co-workers 3 and its CD spectrum was recorded. 4 The characteristic features of the experimental CD spectrum (Fig.…”

mentioning

confidence: 99%

Theoretical CD spectrum calculations of the crown‐ether aralkyl‐ammonium salt complex

et al. 2002

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“…We also prepared enantiopure crown ethers containing acridine [41] and phenazine [41,45] subcyclic units (see Fig. 11).…”

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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“…Synthesis and molecular recognition studies of many crown ethers based on tricyclic heterocycles are reported in the literature, for example those of xanthone 10 -, dibenzofuran [11][12][13][14] -, phenanthroline [15][16][17][18][19][20][21][22] -, phenazine [23][24][25][26][27] -, or acridone-and acridine 23,[28][29][30][31][32][33][34][35][36][37] -based macrocycles. In the continuation of our research of crown ethers based on tricyclic ring systems, [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] our attention turned toward phenothiazine. The properties of the nitrogen of phenothiazine can not only be modified by substitution in the aromatic rings, but also by changing the oxidation state of the sulfur atom making it a promising building element of new macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 18-crown-6 type ligands containing a phenothiazine 5,5-dioxide unit

Kormos¹,

Sveiczer²,

Fődi³

et al. 2013

Arkivoc

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Enantiomerically pure chiral phenazino-crown ethers: synthesis, preliminary circular dichroism spectroscopic studies and complexes with the enantiomers of 1-arethyl ammonium salts

Cited by 38 publications

References 25 publications

Theoretical CD spectrum calculations of the crown‐ether aralkyl‐ammonium salt complex

Theoretical CD spectrum calculations of the crown‐ether aralkyl‐ammonium salt complex

Synthesis and molecular recognition studies of crown ethers

Synthesis of novel 18-crown-6 type ligands containing a phenothiazine 5,5-dioxide unit

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