New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents

Baczko, Krystyna; Larpent, Chantal; Lesot, Philippe

doi:10.1016/j.tetasy.2004.01.022

Cited by 35 publications

(27 citation statements)

References 47 publications

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“…Methanol (99%), n ‐hexane (99%), and all the other solvents were purchased from Sinopharm and were used as received otherwise denoted. 4‐Isocyanobenzoyl‐2‐aminoisobutyric acid decyl ester ( 3 ) was synthesized according to literature procedures . The chemical structure was confirmed by proton nuclear magnetic resonance spectroscopy ( 1 H NMR) and Fourier transform infrared (FTIR) spectra, as shown in Supporting Information Figure S1.…”

Section: Methodsmentioning

confidence: 99%

One‐pot synthesis of conjugated poly(3‐hexylthiophene)‐b‐poly(phenyl isocyanide) hybrid rod–rod block copolymers and its self‐assembling properties

Liu

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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In this article, the synthesis of a series of conjugated rod–rod block copolymers based on poly(3‐hexylthiophene) (P3HT) and poly(phenyl isocyanide) (PPI) building blocks in a single pot is presented. Ni‐catalyzed Grignard metathesis polymerization of 2,5‐dibromo‐3‐hexylthiophene and subsequent addition of 4‐isocyanobenzoyl‐2‐aminoisobutyric acid decyl ester in the presence of Ni(dppp)Cl2 as a single catalyst afford P3HT‐b‐PPI with tunable molecular weights and compositions. In solid state, microphase separation occurred as differential scanning calorimetric analysis of P3HT‐b‐PPI revealed two glass transition temperatures. In solutions, the copolymers can self‐assemble into spherical aggregates with P3HT core and PPI shell in tetrahydrofuran and exhibit amorphous state in CHCl3. However, atomic force microscopy revealed that the block copolymers self‐assemble into nanofibrils on the substrate. These unique features warrant the resultant conjugated rod–rod copolymers' potential study in organic photovoltaic and other electronic devices. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2939–2947

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Section: Methodsmentioning

confidence: 99%

One‐pot synthesis of conjugated poly(3‐hexylthiophene)‐b‐poly(phenyl isocyanide) hybrid rod–rod block copolymers and its self‐assembling properties

Liu

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…The synthesis and characterization of 1 and 2 have been reported in a previous paper. 23 Compounds 3 25 and 4 26 were prepared according to reported methods. The methods for the determination of association constants have been reported in previous papers.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Bonded Semi‐Rigidified Bispyridyl‐Incorporating Aryl Amide Oligomers: Efficient "C"‐Styled Receptors for Aliphatic Ammoniums, a Remarkable Protonation Effect and Chiral Induction

Gao

et al. 2007

Chin. J. Chem.

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The complexing behaviour of two linear compounds 1 and 2 toward the trifluoroacetic acid (TFA) salts of n-dodecylamine, di-n-octylamine, n-dodecyl D-and L-phenylalaninates (3, 4, and D-and L-5) in chloroform has been described. Compounds 1 and 2 consist of two folded amide moieties with two pyridyls at the terminals which are connected directly or with an acetylene linker. The rigidified folded moieties are stabilized by intramolecular hydrogen bonding, while the whole molecules can adopt an "S"-or a "C"-styled conformation depending on the relative orientation of the two rigidified moieties.1 H NMR, UV-Vis, fluorescent and circular dichroism investigations revealed that 1 and 2 could bind primary and secondary ammonium cations with their "C"-styled conformation. In the presence of 1 equiv. of TFA, the binding stability was increased significantly as a result of promoted formation of the "C"-styled conformation due to the monoprotonation of the peripheral pyridyl units in 1 and 2. In contrast, the addition of 2 equiv. of TFA substantially weakened the binding stability because the "S"-styled conformation was favored as a result of protonation of both of their pyridyl units. Moreover, remarkable induced circular dichroisms were also displayed for the complexes of 1 and 2 with chiral D-and L-5.

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“…10 Compound 60 displays lower solubility and a lower cmc compared to its analogues (e.g., entry 62, Table 1) suggesting a hydrophobic contribution of the benzyl moiety. 2 Surfactant 63 displays a large value of cmc due to the short alkyl chain of six carbon atoms. Surfactant 117 belongs to the branched alkyl sulfates class.…”

Section: General Qspr Model For 181 Anionic Surfactantsmentioning

confidence: 99%

QSPR Study of Critical Micelle Concentration of Anionic Surfactants Using Computational Molecular Descriptors

Katritzky

Pacureanu

Dobchev

et al. 2007

J. Chem. Inf. Model.

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A data set of 181 diverse anionic surfactants has been investigated to relate the logarithm of critical micelle concentration (cmc) to the molecular structure using Comprehensive Descriptors for Structural and Statistical Analysis (CODESSA Pro) software. A fragment approach provided superior quantitative structure-property relationship (QSPR) models in terms of statistical characteristics and predictive ability. The regression equations provided insight into the structural features of surfactants that influence cmc. The most obvious influence on cmc was manifested by hydrophobic fragments expressed by the topological and geometrical descriptors, while the hydrophilic fragment is represented by constitutional, geometrical, and charge related descriptors. Significantly important molecular descriptors in the selected QSPR models were topological, solvational, and charge-related descriptors as the driving force of the intermolecular interactions between anionic surfactants and water.

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New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents

Cited by 35 publications

References 47 publications

One‐pot synthesis of conjugated poly(3‐hexylthiophene)‐b‐poly(phenyl isocyanide) hybrid rod–rod block copolymers and its self‐assembling properties

One‐pot synthesis of conjugated poly(3‐hexylthiophene)‐b‐poly(phenyl isocyanide) hybrid rod–rod block copolymers and its self‐assembling properties

Hydrogen Bonded Semi‐Rigidified Bispyridyl‐Incorporating Aryl Amide Oligomers: Efficient "C"‐Styled Receptors for Aliphatic Ammoniums, a Remarkable Protonation Effect and Chiral Induction

QSPR Study of Critical Micelle Concentration of Anionic Surfactants Using Computational Molecular Descriptors

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