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

Research output: Contribution to journalArticlepeer-review

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, 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).

Original languageEnglish
Pages (from-to)8150-8160
Number of pages11
JournalJournal of the American Chemical Society
Volume137
Issue number25
DOIs
Publication statusPublished - 1 Jul 2015

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