NBN- and BNB-Phenalenyls: the Yin and Yang of Heteroatom-doped π Systems.

NBN- and BNB-doped phenalenyls are isoelectronic to phenalenyl anions and cations, respectively. They represent a pair of complementary molecules that have essentially identical structures but opposite properties as electron donors and acceptors. The NBN-phenalenyls 1-4 considered here were prepared from N,N'-dimethyl-1,8-diaminonaphthalene and readily available boron-containing building blocks (i.

BNB-Doped Phenalenyls: Modular Synthesis, Optoelectronic Properties, and One-Electron Reduction.

A highly modular synthesis of BNB- and BOB-doped phenalenyls is presented. Treatment of the 1,8-naphthalenediyl-bridged boronic acid anhydride with LiAlH/MeSiCl afforded the corresponding 1,8-naphthalenediyl-supported diborane(6) , which served as the starting material for all subsequent transformations. Upon addition of MesMgBr/MeSiCl, was readily converted to the tetraorganyl diborane(6) .

En Route to Stimuli-Responsive Boron-, Nitrogen-, and Sulfur-Doped Polycyclic Aromatic Hydrocarbons.

Replacing both meso carbon atoms of the polycyclic aromatic hydrocarbon (PAH) bisanthene by boron atoms creates an efficient blue fluorophore with a strong electron-accepting character. The corresponding meso-B,S-doped bisanthene exhibits a solvent-dependent green-to-orange photoluminescence and undergoes a reversible reduction at E1/2 =-2.06 V (vs.