Synthesis and characterisation of a new naphthalene tris-Tröger’s base derivative—a chiral molecular clip

Serial tris-Tröger’s base derivatives (trisTBs) are members of a recently introduced family of chiral molecular clips. Naphthalene tris-Tröger’s base is prepared via both stepwise and one-pot approaches. All three diastereoisomers are isolated and unambiguously identified, and their NMR spectra, enantioseparation and binding ability are studied. The syn,syn-trisTB diastereoisomer, a molecular clip, is found to be a potential molecular receptor of electron-deficient cyanobenzenes. For the first time, racemic syn,syn-trisTB is resolved via preparative HPLC (chiral column) and the absolute configurations are assigned by comparison of experimental and calculated ECD spectra. General dependencies on the oligoTB stability in acid media and potential anion binding are suggested.