Solvent Molding of Organic Morphologies Made of Supramolecular Chiral Polymers

Luka Dordević, Tomas Marangoni, Tanja Miletić, Jenifer Rubio-Magnieto, John Mohanraj, Heinz Amenitsch, Dario Pasini, Nikos Liaros, Stelios Couris, Nicola Armaroli, Mathieu Surin, Davide Bonifazi

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

The self-assembly and self-organization behavior of uracil-conjugated enantiopure (R)- or (S)-1,1′-binaphthyl-2,2′-diol (BINOL) and a hydrophobic oligo(p-phenylene ethynylene) (OPE) chromophore exposing 2,6-di(acetylamino)-pyridine termini are reported. Systematic spectroscopic (UV-vis, CD, fluorescence, NMR, and SAXS) and microscopic studies (TEM and AFM) showed that BINOL and OPE compounds undergo triple H-bonding recognition, generating different organic nanostructures in solution. Depending on the solvophobic properties of the liquid media (toluene, CHCl<inf>3</inf>, CHCl<inf>3</inf>/CHX, and CHX/THF), spherical, rod-like, fibrous, and helical morphologies were obtained, with the latter being the only nanostructures expressing chirality at the microscopic level. SAXS analysis combined with molecular modeling simulations showed that the helical superstructures are composed of dimeric double-cable tape-like structures that, in turn, are supercoiled at the microscale. This behavior is interpreted as a consequence of an interplay among the degree of association of the H-bonded recognition, the vapor pressure of the solvent, and the solvophobic/solvophilic character of the supramolecular adducts in the different solutions under static and dynamic conditions, namely solvent evaporation conditions at room temperature. (Chemical Equation Presented).

langue originaleAnglais
Pages (de - à)8150-8160
Nombre de pages11
journalJournal of the American Chemical Society
Volume137
Numéro de publication25
Les DOIs
étatPublié - 1 juil. 2015

Empreinte digitale

Nanostructures
Molding
Polymers
Vapor Pressure
Molecular modeling
Uracil
Chirality
Toluene
Chromophores
Vapor pressure
Pyridine
Tapes
Self assembly
Evaporation
Cables
Fluorescence
Nuclear magnetic resonance
Association reactions
Transmission electron microscopy
Temperature

Citer ceci

Dordević, Luka ; Marangoni, Tomas ; Miletić, Tanja ; Rubio-Magnieto, Jenifer ; Mohanraj, John ; Amenitsch, Heinz ; Pasini, Dario ; Liaros, Nikos ; Couris, Stelios ; Armaroli, Nicola ; Surin, Mathieu ; Bonifazi, Davide. / Solvent Molding of Organic Morphologies Made of Supramolecular Chiral Polymers. Dans: Journal of the American Chemical Society. 2015 ; Vol 137, Numéro 25. p. 8150-8160.
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abstract = "The self-assembly and self-organization behavior of uracil-conjugated enantiopure (R)- or (S)-1,1′-binaphthyl-2,2′-diol (BINOL) and a hydrophobic oligo(p-phenylene ethynylene) (OPE) chromophore exposing 2,6-di(acetylamino)-pyridine termini are reported. Systematic spectroscopic (UV-vis, CD, fluorescence, NMR, and SAXS) and microscopic studies (TEM and AFM) showed that BINOL and OPE compounds undergo triple H-bonding recognition, generating different organic nanostructures in solution. Depending on the solvophobic properties of the liquid media (toluene, CHCl3, CHCl3/CHX, and CHX/THF), spherical, rod-like, fibrous, and helical morphologies were obtained, with the latter being the only nanostructures expressing chirality at the microscopic level. SAXS analysis combined with molecular modeling simulations showed that the helical superstructures are composed of dimeric double-cable tape-like structures that, in turn, are supercoiled at the microscale. This behavior is interpreted as a consequence of an interplay among the degree of association of the H-bonded recognition, the vapor pressure of the solvent, and the solvophobic/solvophilic character of the supramolecular adducts in the different solutions under static and dynamic conditions, namely solvent evaporation conditions at room temperature. (Chemical Equation Presented).",
author = "Luka Dordević and Tomas Marangoni and Tanja Miletić and Jenifer Rubio-Magnieto and John Mohanraj and Heinz Amenitsch and Dario Pasini and Nikos Liaros and Stelios Couris and Nicola Armaroli and Mathieu Surin and Davide Bonifazi",
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Dordević, L, Marangoni, T, Miletić, T, Rubio-Magnieto, J, Mohanraj, J, Amenitsch, H, Pasini, D, Liaros, N, Couris, S, Armaroli, N, Surin, M & Bonifazi, D 2015, 'Solvent Molding of Organic Morphologies Made of Supramolecular Chiral Polymers', Journal of the American Chemical Society, VOL. 137, Numéro 25, p. 8150-8160. https://doi.org/10.1021/jacs.5b02448

Solvent Molding of Organic Morphologies Made of Supramolecular Chiral Polymers. / Dordević, Luka; Marangoni, Tomas; Miletić, Tanja; Rubio-Magnieto, Jenifer; Mohanraj, John; Amenitsch, Heinz; Pasini, Dario; Liaros, Nikos; Couris, Stelios; Armaroli, Nicola; Surin, Mathieu; Bonifazi, Davide.

Dans: Journal of the American Chemical Society, Vol 137, Numéro 25, 01.07.2015, p. 8150-8160.

Résultats de recherche: Contribution à un journal/une revueArticle

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T1 - Solvent Molding of Organic Morphologies Made of Supramolecular Chiral Polymers

AU - Dordević, Luka

AU - Marangoni, Tomas

AU - Miletić, Tanja

AU - Rubio-Magnieto, Jenifer

AU - Mohanraj, John

AU - Amenitsch, Heinz

AU - Pasini, Dario

AU - Liaros, Nikos

AU - Couris, Stelios

AU - Armaroli, Nicola

AU - Surin, Mathieu

AU - Bonifazi, Davide

PY - 2015/7/1

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N2 - The self-assembly and self-organization behavior of uracil-conjugated enantiopure (R)- or (S)-1,1′-binaphthyl-2,2′-diol (BINOL) and a hydrophobic oligo(p-phenylene ethynylene) (OPE) chromophore exposing 2,6-di(acetylamino)-pyridine termini are reported. Systematic spectroscopic (UV-vis, CD, fluorescence, NMR, and SAXS) and microscopic studies (TEM and AFM) showed that BINOL and OPE compounds undergo triple H-bonding recognition, generating different organic nanostructures in solution. Depending on the solvophobic properties of the liquid media (toluene, CHCl3, CHCl3/CHX, and CHX/THF), spherical, rod-like, fibrous, and helical morphologies were obtained, with the latter being the only nanostructures expressing chirality at the microscopic level. SAXS analysis combined with molecular modeling simulations showed that the helical superstructures are composed of dimeric double-cable tape-like structures that, in turn, are supercoiled at the microscale. This behavior is interpreted as a consequence of an interplay among the degree of association of the H-bonded recognition, the vapor pressure of the solvent, and the solvophobic/solvophilic character of the supramolecular adducts in the different solutions under static and dynamic conditions, namely solvent evaporation conditions at room temperature. (Chemical Equation Presented).

AB - The self-assembly and self-organization behavior of uracil-conjugated enantiopure (R)- or (S)-1,1′-binaphthyl-2,2′-diol (BINOL) and a hydrophobic oligo(p-phenylene ethynylene) (OPE) chromophore exposing 2,6-di(acetylamino)-pyridine termini are reported. Systematic spectroscopic (UV-vis, CD, fluorescence, NMR, and SAXS) and microscopic studies (TEM and AFM) showed that BINOL and OPE compounds undergo triple H-bonding recognition, generating different organic nanostructures in solution. Depending on the solvophobic properties of the liquid media (toluene, CHCl3, CHCl3/CHX, and CHX/THF), spherical, rod-like, fibrous, and helical morphologies were obtained, with the latter being the only nanostructures expressing chirality at the microscopic level. SAXS analysis combined with molecular modeling simulations showed that the helical superstructures are composed of dimeric double-cable tape-like structures that, in turn, are supercoiled at the microscale. This behavior is interpreted as a consequence of an interplay among the degree of association of the H-bonded recognition, the vapor pressure of the solvent, and the solvophobic/solvophilic character of the supramolecular adducts in the different solutions under static and dynamic conditions, namely solvent evaporation conditions at room temperature. (Chemical Equation Presented).

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