Supramolecular optical chemosensors are abiotic molecular devices that bind analytes by noncovalent interactions, producing a change in light absorption or fluorescence. This review summarizes recent progress in the development of such chemosensors for organic analytes based on artificial receptors. Important design considerations, such as analyte affinity, choice of chromophore or fluorophore, binding selectivity, and optical signaling mechanism are briefly discussed. Chemists have fashioned chemosensors from a wide range of molecular structures, including polyalcohols, crown ethers, calixarenes, helicenes, sterically geared tripods, metal complexes, pinwheels, porphyrins, and fused-ring heterocycles. Analytes of interest include amines, carboxylic acids, amino acids, hydroquinones, alkaloids, carbohydrates, peptides, urea and creatinine.

Infinite channels with a diameter 10.5 Å are formed by the DNA‐base hybrid 1 in the solid state. These channels arise because 1 specifically communicates the hydrogen bonding codes of the nucleobases cytosine and guanine (“C” and “G”) to unambiguously assemble hexagonal, macrocyclic aggregates 16, which overlap in the crystal.

Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.

Monocyclic medium-ring diamines whose monoprotonated ions can form transannular hydrogen bonds have enhanced basicities in solution; structural data for 1,6-dimethyl-l,6-diazacyclodecane suggest that the enhanced basicity may reflect steric inhibition of solvation, leading to gas-phase-like behaviour.