Darstellung und optische Eigenschaften endständig substituierter Polyene mit Androstan als Spacer

Abstract

The conjugated polyenes 10, 11, 21, 22, and 26 with 9-anthryl and 2-tetraphenylporphyrinyl (TPP) terminal groups and an androstane unit incorporated into the polyene chain were synthesized by Wittig or Wittig-type olefinations. In most but not all cases the desired all-(E) isomers could be obtained from the (E)/(Z)-isomeric mixtures by chromatographic purification. From the UV/Vis spectra it is concluded that in all cases the TPP group and the polyene chain are electronically separated, whereas the 9-anthryl residue and the connected dienyl moiety in 10 and 11 are electronically amalgamated. In 21, 22, and 26 a selective excitation of the anthryl group, the TPP moiety, and the polyene is possible.