title: Solvent Molding of Organic Morphologies Made of Supramolecular Chiral Polymers.
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.
authors.affiliation: †Department of Chemical and Pharmaceutical Sciences, INSTM UdR Trieste, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy.
authors.forename: Luka
authors.initials: L
authors.lastname: Đorđević
authors.affiliation: †Department of Chemical and Pharmaceutical Sciences, INSTM UdR Trieste, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy.
authors.forename: Tomas
authors.initials: T
authors.lastname: Marangoni
authors.affiliation: †Department of Chemical and Pharmaceutical Sciences, INSTM UdR Trieste, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy.
authors.forename: Tanja
authors.initials: T
authors.lastname: Miletić
authors.affiliation: §Laboratory for Chemistry of Novel Materials, Center for Innovation in Materials and Polymers, University of Mons-UMONS, 20 Place du Parc, B-7000 Mons, Belgium.
authors.forename: Jenifer
authors.initials: J
authors.lastname: Rubio-Magnieto
authors.affiliation: ⊥Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via Gobetti 101, 40129 Bologna, Italy.
authors.forename: John
authors.initials: J
authors.lastname: Mohanraj
authors.affiliation: ∥Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria.
authors.forename: Heinz
authors.initials: H
authors.lastname: Amenitsch
authors.affiliation: #Department of Chemistry and INSTM UdR Pavia, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy.
authors.forename: Dario
authors.initials: D
authors.lastname: Pasini
authors.affiliation: ×Department of Physics, University of Patras, 26504 Patras, Greece.|∇Institute of Chemical Engineering Sciences, Foundation for Research and Technology-Hellas, P.O. Box 1414, Patras 26504, Greece.
authors.forename: Nikos
authors.initials: N
authors.lastname: Liaros
authors.affiliation: ×Department of Physics, University of Patras, 26504 Patras, Greece.|∇Institute of Chemical Engineering Sciences, Foundation for Research and Technology-Hellas, P.O. Box 1414, Patras 26504, Greece.
authors.forename: Stelios
authors.initials: S
authors.lastname: Couris
authors.affiliation: ⊥Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via Gobetti 101, 40129 Bologna, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Armaroli
authors.affiliation: §Laboratory for Chemistry of Novel Materials, Center for Innovation in Materials and Polymers, University of Mons-UMONS, 20 Place du Parc, B-7000 Mons, Belgium.
authors.forename: Mathieu
authors.initials: M
authors.lastname: Surin
authors.affiliation: †Department of Chemical and Pharmaceutical Sciences, INSTM UdR Trieste, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy.|⊗Namur Research College and Department of Chemistry, University of Namur-UNamur, Rue de Bruxelles 61, 5000 Namur, Belgium.
authors.forename: Davide
authors.initials: D
authors.lastname: Bonifazi