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Isophthalic and terephthalic acid monoesters of cyclic nigerosyl‐(1→6)‐nigerose (CNN), a cyclic tetrasaccharide composed of four d‐glucopyranosyl residues connected by alternating α‐1,3‐ and α‐1,6‐linkages, were synthesized as novel chiral supramolecular sensitizers for enantiodifferentiating photoisomerization of (Z)‐cyclooctene (1Z) to planar chiral (E)‐isomer (1E). Despite the saucer‐shaped shallow...
Enantiopure hemicryptophanes efficiently discriminate chiral ammonium neurotransmitters. The ephedrine and norephedrine molecules associate with hemicryptophane hosts to form 1:1 and 1:2 host‐guest complexes. Binding constants are determined by fitting the 1H nuclear magnetic resonance (NMR) titration curves to give β1 and β2 values, which are used to characterize the diastereomeric and enantiomeric...
Bis(diamido)‐bridged basket resorcin[4]arene (all-S)-1 and its (all-R)-1 enantiomer proved able to interact with 2'‐deoxycytidine (2) and pyrimidine nucleoside analogs in dimethyl sulfoxide (DMSO) solution. In such a solvent, the resorcinarene hosts adopt a preferential 1,3‐alternate‐like conformation, with a larger cavity delimited by two syn 3,5‐dimethoxyphenyl moieties, and two external pockets,...
This review brings together the past and current methods for synthesizing the classical cucurbit[n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as " classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methylene bridging carbons. The synthetic background and general physical and...
There are frequent situations both in supramolecular chemistry and in crystallography that result in stereogenic centers, whose absolute configuration needs to be specified. With this aim we propose the inclusion of one simple additional rule to the Cahn‐Ingold‐Prelog (CIP) system of priority rules stating that noncovalent interactions have a fictitious number between 0 and 1. Chirality 27:339–343, 2015...
We studied the spontaneous formation of chiral crystals of four diaryl ethers, 3‐phenoxybenzaldehyde, 1; 1,3‐dimethyl‐2‐phenoxybenzene, 2; di(4‐aminophenyl) ether, 3; and di(p‐tolyl) ether, 4. Compounds 1, 3, and 4 form conformationally chiral molecules in the solid state, while the chirality of 2 arises from the formation of supramolecular helices. Compound 1 is a liquid at ambient temperature, but...
Helical D3tris(4‐amino‐2,6‐pyridine‐dicarboxylate)terbium(III) and europium(III) complexes, which form a racemic equilibrium in aqueous solution, were prepared to study their secondary coordination sphere interactions with chiral amino acids. These interactions were probed using a combination of circularly polarized luminescence (CPL) and 13C NMR spectroscopy. The results indicate that, regardless...
The use of stereodynamic probes is becoming one of the leading strategies for the fast and effective determination of enantiomeric excess. Recently, we reported a series of novel molecular architectures based on a modified tris(2‐pyridylmethyl)amine complex (TPMA), which are able to amplify the electronic CD, in the case of Zn(II) assemblies and vibrational CD, in the case of Co(II) assemblies. Herein,...
Tripodal metal complexes have been widely used for catalysis and more recently also for molecular recognition applications. Their ability in recognition and signal amplification of chiral substrates is because of the setup of the ligand around the metal in a propeller shape. Within this subject, we have recently reported tris(2‐pyridylmethyl)amine‐ and triphenolamine‐based complexes for the determination...
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