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Synthesis and Enantioselective Discrimination of Chiral Fluorescence Receptors Bearing Amino Acid Units 总被引:1,自引:0,他引:1
Two chiral fluorescence receptors (1, 2) were synthesized, and their structures were characterized by IR, ^1H NMR, ^13C NMR, mass spectra and elemental analysis. The chiral recognition of receptors was studied by ^1H NMR and fluorescence spectra. The results demonstrate that receptors and dibenzoyl tartrate anion formed a 1 : 1 complex. The receptor 1 exhibited a good enantioselective recognition ability toward the enantiomers of dibenzoyl tartrate anion. 相似文献
3.
《Tetrahedron: Asymmetry》2007,18(15):1769-1774
The fluorescent photoinduced electron transfer (PET) chemosensors 1–3 based on (S)-1,1′-bi-2-naphthol were designed for their recognition of dibenzoyl tartrate anions. The binding properties for hydroxy acid anions were examined by the fluorescence and 1H NMR spectra. The results indicated that receptor 1 exhibit excellent enantioselectivity toward the enantiomers of dibenzoyl tartrate anion. 相似文献
4.
《Tetrahedron: Asymmetry》2005,16(4):833-839
Two chiral fluorescence receptors 1 and 2 have been synthesized, and their structures characterized by IR, 1H NMR, MS spectra and elemental analysis. The chiral recognition of the receptors was studied by 1H NMR and fluorescence spectra. The results demonstrate that the receptors and tetrabutylammonium mandelate formed a 1:1 complex. Two receptors exhibit good chiral recognition abilities towards the enantiomers of tetrabutylammonium mandelate. 相似文献
5.
《Tetrahedron: Asymmetry》2006,17(22):3144-3151
Two chiral fluorescence receptors 3a and 3b based on calix[4]arenes were synthesized, and their chiral recognition properties for enantiomeric malate were studied by fluorescence and 1H NMR spectra in CHCl3. The addition of either l- or d-malate caused obvious fluorescence quenching of the host solution. Different fluorescent responses demonstrate that the two receptors have good enantioselective recognition abilities towards malate. 相似文献
6.
New chiral receptors 1 and 2 based on (S)-BINOL and thiourea units were synthesized. The chiral recognition of receptors for chiral anions were studied by fluorescence, UV–vis, and 1H NMR spectra. The results of the non-linear curve fitting indicated that the receptors and guest anions formed a 1:1 stoichiometric complex. The obvious color change of receptor 2 can be observed by the naked eye when the enantiomers of mandelate anions were added, which demonstrates that receptor 2 may be used as a colorimetric sensor for mandelate anions. 相似文献
7.
Kuo-xi Xu Zhen Qiu Jin-Jin Zhao Jin Zhao Chao-jie Wang 《Tetrahedron: Asymmetry》2009,20(14):1690-1696
The derivatives of BINOL, (S)-1 and (R)-1, and their analogues have been prepared and the structures of these compounds have been characterized by IR, MS, 1H, and 13C NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and 1H NMR spectroscopy. The receptors exhibited different chiral recognition abilities toward some enantiomers of chiral materials and formed 1:1 complexes between host and guest. Receptor (S)-1 or (R)-1 exhibits excellent enantioselective fluorescent recognition abilities toward amino acid derivatives. 相似文献
8.
Bis (α - diazophenacyl) mercury (2a), bis (α - diazo - 2,4,6 - trimethylphenacyl) mercury (2b), bis (1 - diazo - 3,3 - dimethyl - 2 - oxobutyl)mercury (2c), and bis (1 - diazo - 2 - phenylacetonyl) mercury (2d) have been prepared by treatment of the corresponding α-diazo ketones with mercuric oxide. The solution IR, UV, and 1H NMR spectra of 2a–d and of three other mercuribis (α-diazo ketones) have been compared with the spectra of the corresponding α-diazo ketones, and the similarities between these have led to the conclusion that in solution these mercury derivatives exist with the mercury bonded to carbon. The 13C NMR resonance spectra of 2a and of α-diazo - α - methylmercuriacetophenone (9) have been examined for evidence of 199HgC coupling; this was observed in the case of 9 for the Me carbon, but not detected in either case for the diazo carbon; this is attributed to difficulty of detection and/or ligand exchange. The signals of the diazo carbon in these spectra occur at unusually high field; a similar observation was made in the spectra of several α-diazo ketones, where the chemical shifts were in the range δ 50–70. 相似文献
9.
Zhi-hong Chen Yong-bing He Chen-Guang Hu Xiao-huan Huang 《Tetrahedron: Asymmetry》2008,19(17):2051-2057
Two chiral fluorescent chemosensors 1 and 2 were synthesized, and the structure characterized by IR, 1H NMR, 13C NMR, MS spectra and elemental analysis. Their recognition ability was studied in aqueous solution (Tris–HCl buffer pH 7.4, MeOH/H2O = 1:1) through fluorescence spectra. Receptors 1 and 2 showed a good binding ability to the copper ion. The host 1-Cu2+ complex showed a chiral recognition ability to mandelate anions with a preferable binding to l-mandelate than d-mandelate anions. The host 1-Cu2+ complex and l- or d-mandelate anions formed 1:1 stoichiometric complex. The binding constant for l-mandelate is 576 M−1, whereas that for d-mandelate is only 38 M−1, which can be distinguished by the different change of fluorescence intensity. 相似文献
10.
《Tetrahedron: Asymmetry》2006,17(14):2143-2148
New chiral fluorescence macrocycles 1 and 2 containing naphthalene and amino acid units were synthesized. The binding properties for amino acid anions were examined by the fluorescence and 1H NMR spectra. The results indicated good enantioselectivity of 1 toward the N-protected phenylalanine anions. 相似文献
11.
《Tetrahedron: Asymmetry》2005,16(8):1527-1534
Two novel types of chiral calix[4]arenes containing hydrazide and dansyl groups were synthesized and examined for their enantioselective recognition abilities by the fluorescence and 1H NMR spectra in CHCl3. The results indicate that both 4a and 4b have excellent enantioselectivities to the N-protected alanine or phenylalanine anions. 相似文献
12.
In this work, 3,3′-(((1E,1′E)-(H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(ethene-2,1-diyl))bis(1,1-dimethyl-1H-benzo[e]indole-3-ium-2,3-diyl))bis(propane-1-sulfonate) (1), 3,3’-(((1E,1′E)-(6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(ethene-2,1-diyl))bis(3,3-dimethyl-3H-indole-1-ium-2,1-diyl))bis(propane-1-sulfonate) (2), 2,2’-((1E,1′E)-(6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(ethene-2,1-diyl))bis(1,3,3-trimethyl-3H-indol-1-ium) iodide (3) and 2,2’-((1E,1′E)-(6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(ethene-2,1-diyl))bis(1,1,3-trimethyl-1H-benzo[e]indol-3-ium) iodide (4) were designed and synthesized by ethylene bridging of the N-substituted indolium salts and the Tröger’s Base (TB) framework. The probes exhibited a longer absorption and emission wavelength and the emission wavelength of them in dichloromethane (DCM) was more than 600 nm, performed a red fluorescence. All of the probes could work on the extreme acidic and the extreme alkaline environments and showed a good liner response in the working pH range. Especially, 2 and 4 were soluble in water and manifested a good pH sensing in a water system. Also, 1H NMR analysis illustrated how these dyes worked as the pH-sensitive fluorescence probes. In addition, they performed excellent reversibility, high selectivity and good photostability. 相似文献
13.
Bilge Taner 《Journal of inclusion phenomena and macrocyclic chemistry》2014,79(1-2):75-81
A new vic-dioxime functionalized calix[4]pyrrole was synthesized from anti-chloroglyoxime and 4-aminophenyl-calix[4]pyrrole at room temperature. The Ni(II) complex has been prepared by reacting the ligand with NiCl2·6H2O in ethanol. These receptors were characterized by elemental analyses, 1H and 13C NMR spectra, IR and mass spectra. Electrochemical properties of the ligand, and its Ni(II) complex were investigated in CH2Cl2 solution by cyclic voltammetry at 100 mV s?1 scan rate. Anion-binding studies were carried out using UV–Vis, and 1H NMR titrations, revealed that the Ni(II) complex exhibits selective recognition toward F? over other anions. The selectivity for F– among the halides is attributed mainly to the hydrogen-bond interaction of the receptor with F–. Receptor showed colour change from red to brown in the presence of tetrabutylammonium fluoride (TBAF) with 1:2 stoichiometry. 相似文献
14.
Dong Wang Xiuli Cheng Yuhua Shi Erjun Sun Xuexin Tang Changfu Zhuang Tongshun Shi 《Solid State Sciences》2009,11(1):195-199
The porphyrin nicotinic acid binary compounds with different substituents in porphine rings (5-(4-nicotinicoxyldecyloxy)phenyl-10,15,20-triphenylporhyrin 2a, 5-(4-nicotinicoxyldecyloxy)phenyl-10,15,20-tri(4-chlorophenyl)porphyrin 2b and 5-(4-nicotinicoxyldecyloxy)phenyl-10,15,20-tri(4-methoxyphenyl)porphyrin 2c) were synthesized. All of them have been characterized, assigned and analyzed by UV–vis, IR, MS and 1H NMR spectra. Their electrochemical and spectroscopic properties were studied by using cyclic voltammetry, fluorescence spectra and Resonance Raman spectra. Different substituents have a little influence on electrochemical behavior and fluorescence spectra. In the Resonance Raman spectra, the substituent has little influence on the skeleton vibration of porphyrin and has much influence on the vibration of phenyl. 相似文献
15.
Two linear bis(pyrrol-2-yl-methyleneamine)s linked by a carbon chain, -(CH2)n-, n=2, 4, were synthesized in high yields by condensation of 2-formylpyrrole with the corresponding diamines. Self-assembly of the resulting bis(pyrrol-2-yl-methyleneamine) ligands with Zn(II) gave double-stranded helicates in excellent yields. Their structures were characterized by MS, 1H NMR, 13C NMR, UV-Vis spectroscopic studies, and were confirmed by an X-ray crystal analysis. In CH2Cl2, both complexes 4 and 5 displayed moderate fluorescence. 相似文献
16.
Stereoselective synthesis of pseudotripeptides 4, 5, 6, 8, 9, 13 and 14, incorporating an uncommon bis(α-aminoacid) derivative, has been accomplished starting from the L-valine derived chiral synthon 1. The configuration of the introduced stereogenic centres has been assigned on the basis of 1H NMR spectroscopic data. The geometry of the tripeptides, deduced on the basis of 1H NMR parameters and IR spectra, was confirmed by X-ray crystal structure analysis of 6. 相似文献
17.
Samuel B. Owens Jr. 《Journal of organometallic chemistry》2008,693(26):3907-3914
The syntheses of two chiral bis(phosphite) ligands with tartaric acid-derived backbones: 1 (from dimethyl tartrate) and 2 (from dipyrollidene tartramide), three complexes of 1: cis-Mo(CO)4(1), cis-PtCl2(1), and cis-PdCl2(1) and two complexes of 2: cis-Mo(CO)4(2) and cis-PdCl2(2) are described. Each ligand and complex has been fully characterized by 1H, 13C, and 31P NMR spectroscopy, and the coordination 31P NMR chemical shifts have been compared to those observed for complexes of related ligands. The X-ray crystal structures of each of the metal complexes have also been determined. The X-ray crystal structures indicate that the conformation of the seven-membered chelate ring varies depending on the substituents on the tartrate backbone. However, the conformations of the seven-membered rings do not change when the metal center is changed or when the coordination environment around the metal center is changed. 相似文献
18.
Four cholate-based pyridinium compounds were synthesized and their binding abilities toward unmodified amino acids were investigated by UV spectroscopy and fluorescence emission spectroscopy. Studies revealed that the recognition process involved hydrogen bonding, electrostatic force, and π–π interaction. The receptor 4a was found to recognize l-tryptophan specifically, and the complex was studied by 1H NMR spectroscopy. The receptors 4b and 4c showed very little recognition ability toward l-tryptophan, indicating the important role of the benzyl group at pyridinium ring. 相似文献
19.
Rebecca M. Duke 《Tetrahedron letters》2010,51(41):5402-7844
The quinoxaline 1, possessing a 2,6-pyridyl-based amidothiourea moiety, with the view of forming a pre-organised molecular cleft, was developed as a fluorescent anion sensor. The sensing ability of 1 was evaluated in organic solution where both the ground and the excited state of 1 was affected upon recognition of anions such as acetate [as tetrabutylammonium salt (TBAAc) solution] at the amiodothiourea moieties in MeCN. The fluorescence of 1, with λmax at 477 nm, was, on all occasions quenched, upon anion recognition. Using TBAOH, we also show that the same anion-induced changes occurred; demonstrating that for this particular sensor, the anion-sensing takes place via a deprotonation mechanism. This anion-induced deprotonation event was further investigated by carrying out 1H NMR titrations on 1, using both AcO− and OH− in DMSO-d6. 相似文献