1,8‐Diarylnaphthalenes: Synthesis, Properties, and Applications

Abstract

Abstract1,8‐Diarylnaphthalenes are a fascinating example of strained organic molecules that have found many practical applications due to unusual parallel face‐to‐face arrangement of two peri‐aryl rings in close proximity almost perpendicular to the central naphthalene backbone. 1,8‐Diarylnaphthalenes show notable potential as photoluminescent and chiral sensors, stereodynamic switches, nonlinear optic chromophores, blue‐transparent frequency doublers, materials for creating high‐performance blue and green OLEDs, chiral ligands and so on. Molecules of this type have also been used as convenient models for studying π‐π, dipole‐π and cation‐π interactions. 1,8‐Diarylnaphthalenes are also interesting as objects to study atropisomeric transformations: if the peri‐aryl rings have ortho‐ or meta‐substituents, then the anti‐conformer becomes C2‐symmetrical (hence chiral), and the syn‐isomer upon symmetrical substitution is achiral. In this review, data on synthetic methods, applications, atropisomerism and structural characteristics of 1,8‐diaryl‐ and 1,8‐dihetarylnaphthalenes are summarized.