Alternating, all-trans polyenynes: Model compounds for poly(diacetylene)s with defined conjugation length

The syntheses of polyenynes as model compounds for poly(diacetylene)s (PDAs) are described. Variation of properties (UV–VIS, Raman, NMR and bond geometries) as a function of the chain length was investigated. After extrapolation to infinite chain length these data were compared to those for PDAs. From UV–VIS spectra a value of λ = 551 nm (2.25 eV) was calculated corresponding to the electronic transition of a single polyenyne chain. This energy is located at the low energy end of a yellow PDA solution spectrum. From Raman scattering v(CC) = 2108–2128 cm−1 and v(CC) = 1505–1532 cm−1 were calculated after extrapolation. Similarly sp‐C13C NMR data yielded a shift of δ = 100 ppm. These data are almost identical to data known for yellow PDA solutions. Bond geometries are almost identical to those of poly(diacetylene)s and theoretical data.