Synthesis, Structure, and Nonlinear Optical Properties of Diarylpolyynes

A series of α,ω-diarylpolyynes has been synthesized. In addition to the synthesis of three hexaynes (3a − c), a notably improved synthesis of 1,16-diphenylhexadecaoctayne (5) is described. The third-order nonlinear optical characteristics for these molecules have been studied and show a substantial increase in molecular hyperpolarizability (γ) as a function of increasing length. The unusual solid-state structures of compounds 3a and 3b are reported.