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Solvent molding of organic morphologies made of supramolecular chiral polymers

Đorđević, Luka, Marangoni, Tomas, Miletic, Tanja, Rubio-Magnieto, Jenifer, Mohanraj, John, Amenitsch, Heinz, Pasini, Dario, Liaros, Nikos, Couris, Stelios, Armaroli, Nicola, Surin, Mathieu and Bonifazi, Davide 2015. Solvent molding of organic morphologies made of supramolecular chiral polymers. Journal of the American Chemical Society 137 (25) , pp. 8150-8160. 10.1021/jacs.5b02448

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Last Modified: 08 Sep 2020 16:00

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