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

Abstract

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 periaryl 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 metasubstituents, then the anti-conformer becomes C 2 -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.

Synthesis, conformational stability and molecular structure of 4-aryl- and 4,5-diaryl-1,8-bis(dimethylamino)naphthalenes

“…1,8-Diarylnaphthalenes 1 have attracted considerable attention from organic, physical organic and material chemists for decades due to their unusual geometry and, consequently, properties. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] It is well known that in the absence of any steric restrictions, two aryl rings prefer the T-arrangement based on the electrostatic interaction between the π-system of one ring and the polarized C-H bond of the other ring. 15,16 The peri-aryl nucleus of 1,8-diarylnaphthalenes exhibits an unfavorable face-to-face orientation almost perpendicular to the central naphthalene core causing severe repulsion between stacked rings and structural deformation of the central naphthalene skeleton.…”