Supramolecular-Directed Chiral Induction in Biaryl Derivatives

Etxebarría, J.; Degenbeck, H.; Felten, Anne‐Sophie; Serres, S.; Nieto, Natalia; Vidal‐Ferran, Anton

doi:10.1021/jo9015425

Cited by 29 publications

(28 citation statements)

References 35 publications

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“…[10][11][12][13] So far, the stereochemistry of these ligands has been controlled via hydrogen bonding, 14 hydrogen bonding and formation of supramolecular structures, [15][16][17] coordination of additional chiral coligands, 18 chiral counter-ions, 19,20 and chiral ionic liquids. [10][11][12][13] So far, the stereochemistry of these ligands has been controlled via hydrogen bonding, 14 hydrogen bonding and formation of supramolecular structures, [15][16][17] coordination of additional chiral coligands, 18 chiral counter-ions, 19,20 and chiral ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular chirality transfer in a stereodynamic catalysts

Storch

Trapp

2018

Chirality

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We present rhodium catalysts that contain stereodynamic axially chiral biphenol-derived phosphinite ligands modified with non-stereoselective amides for non-covalent interactions. A chirality transfer was achieved with (R)- or (S)-acetylphenylalanine methyl amide, and the interaction mechanism was investigated by NMR measurements. These interactions at the non-stereoselective interaction sites and the formation of supramolecular complexes result in an enrichment of either the (R )- or (S ) enantiomer of the tropos catalysts, which in turn provide the (R)- or (S)-acetylphenylalanine methyl ester in the hydrogenation of (Z)-methyl-α-acetamidocinnamate.

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Section: Introductionmentioning

confidence: 99%

Supramolecular chirality transfer in a stereodynamic catalysts

Storch

Trapp

2018

Chirality

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“…2015, 53, 1431-1439 INTRODUCTION Among the various photovoltaic technologies under development, one of the contemporary areas is the polymer solar cells that are quite pertinent for the cost effective and user friendly method of generating electricity from the sun light. [1][2][3] Main attractions of polymer solar cells lie in the suitability of inexpensive, low temperature solution processing techniques like spin coating, drop casting, printing, and so forth for large area fabrication. [1][2][3] In addition, other advantages like lightweight, flexibility, and the ability to tune the properties through organic synthesis methods have also made the polymer solar cells attractive.…”

mentioning

confidence: 99%

“…[1][2][3] Main attractions of polymer solar cells lie in the suitability of inexpensive, low temperature solution processing techniques like spin coating, drop casting, printing, and so forth for large area fabrication. [1][2][3] In addition, other advantages like lightweight, flexibility, and the ability to tune the properties through organic synthesis methods have also made the polymer solar cells attractive. [1][2][3] Despite these advantages, the commercialization of the polymer solar cells is hampered due to the poor efficiency 1,4 and stability of materials/devices.…”

mentioning

confidence: 99%

“…[1][2][3] In addition, other advantages like lightweight, flexibility, and the ability to tune the properties through organic synthesis methods have also made the polymer solar cells attractive. [1][2][3] Despite these advantages, the commercialization of the polymer solar cells is hampered due to the poor efficiency 1,4 and stability of materials/devices. [5][6][7][8] One of the important factors that determines the efficiency of such solar cells is the film morphology of the active layer in the bulk heterojunction devices.…”

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confidence: 99%

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Charge transport properties of MDMO PPV thin films cast in different solvents

Mohan

Joshi

Shalu

et al. 2015

J Polym Sci B Polym Phys

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Charge transport properties in thin films of Poly(2‐methoxy‐5‐(3′,7′‐dimethyloctyloxy)‐1,4‐phenylenevinylene) (MDMO PPV) cast using either chloroform (CF), toluene (TOL), or chlorobenzene (CB) as solvent were investigated. Hole mobility (μ) in these thin films measured using time‐of‐flight transient photoconductivity showed an increasing trend with respect to the solvent used in the same order, that is, μCF (2.4 × 10−7 cm2/Vs) < μTOL (6.9 × 10−7 cm2/Vs) < μCB (2.3 × 10−6 cm2/Vs). Observed variations in mobilities were attributed to different morphologies of MDMO PPV chains in thin films cast using the aforesaid solvents. Nature of the interchain interactions and aggregate formation were obtained using photoluminescence (PL), Raman spectroscopy, and AFM studies. Ratio of PL peak intensities of 0–0 and 0–1 transitions, which is a direct measure of interchain interaction, was the highest in CB and lowest in CF. Variation in the relative intensities of out‐of‐plane wagging of vinylene group (∼963 cm−1 mode) in Raman spectra suggested different extent of coiling of polymer chains in these thin films. From these observations, it was elicited that aggregate size and interchain interactions are highest in CB and least in CF. AFM‐based topographic images of thin films further supported these variations in the size of aggregates. Variation in the aggregate sizes and interchain interactions explained the corresponding variation in the mobility. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2015, 53, 1431–1439

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“…Catalyst 6 embodies these elements. Peptide 6 contains the dimethylamino-alanine residue (Dmaa), which we felt might target the acidic meta -hydroxyl of the benzamide, 14 possibly activating the arene. We elected to embed Dmaa within peptide frameworks we have examined extensively over the years.…”

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confidence: 99%

Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination

2013

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We report the enantioselective synthesis of atropisomeric benzamides employing catalytic electrophilic aromatic substitution reactions involving bromination. The catalyst is a simple tetrapeptide bearing a tertiary amine that may function as a Brønsted base. A series of tri- and dibrominations are accomplished for a range of compounds bearing differential substitution patterns. Tertiary benzamides represent appropriate substrates for the reaction since they exhibit sufficiently high barriers to racemization after ortho-functionalization. Mechanism-driven experiments provide some insight into the basis for selectivity. Examination of the observed products at low conversion suggests that the initial catalytic bromination may be regioselective and stereochemistry-determining. A complex between catalyst and substrate is observed by NMR, revealing a specific association. Finally, products of these reactions may be subjected to regioselective metal-halogen exchange and trapping with I2, setting the stage for utility.

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Supramolecular-Directed Chiral Induction in Biaryl Derivatives

Cited by 29 publications

References 35 publications

Supramolecular chirality transfer in a stereodynamic catalysts

Supramolecular chirality transfer in a stereodynamic catalysts

Charge transport properties of MDMO PPV thin films cast in different solvents

Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination

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