TY - JOUR A1 - Caricato, Marco A1 - González, Silvia Díez A1 - Arandia Ariño, Idoia A1 - Pasini, Dario T1 - Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 JF - Beilstein Journal of Organic Chemistry PY - 2014/// VL - 10 SP - 1308 EP - 1316 SN - 1860-5397 DO - 10.3762/bjoc.10.132 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.10.132 KW - BINOL KW - C60 KW - carbon nanomaterials KW - carbon nanostructures KW - chirality KW - macrocycles KW - sensors KW - supramolecular chemistry N2 - The “one-pot” synthesis of several homochiral macrocycles has been achieved by using π-electron-rich, electron-deficient or extended aromatic dicarboxylic acids in combination with an axially-chiral dibenzylic alcohol, derived from enantiomerically-pure BINOL. Two series of cyclic adducts with average molecular D2 and D3 molecular symmetries, respectively, have been isolated in pure forms. Their yields and selectivities deviate substantially from statistical distributions. NMR and CD spectroscopic methods are efficient and functional in order to highlight the variability of shapes of the covalent macrocyclic frameworks. The larger D3 cyclic adducts exhibit recognition properties towards C60 in toluene solutions (up to log Ka = 3.2) with variable stoichiometries and variable intensities of the charge-tranfer band upon complexation. ER -