Abstract
The present paper deals with the synthesis of oligo(1,4-phenylenevinylene)s (trimers, tetramers and a nonamer), which contain 1-3 (E)-stilbene crowns. A classical reaction route led first to stilbene crown subunits. Wittig-Horner reactions of diphosphonates with mono- or dialdehydes or of dialdehydes with mono- or diphosphonates yielded then the desired all-trans configured OPVs, which were designed for the complexation of metal cations.
Highlights
Among the conjugated oligomers, 1,4-phenylenevinylenes, OPVs (1) are prominent examples with various applications in materials science, such as light emitting diodes (LEDs), semiconductive or photoconductive devices, nonlinear optics, conversion of sunlight, formation of liquid crystals, etc
We studied the preparation of OPVs 1 (m = 3, 4, 9), which contain crown ether segments of type 2 (n = 1, 3), which can be called stilbene crowns
In order to get OPV crowns, we synthesized first the stilbene crowns 8a,b and 9a,b (Scheme 1), which bear substituents, that are suitable for the extension of the conjugated chain
Summary
1,4-phenylenevinylenes, OPVs (1) are prominent examples with various applications in materials science, such as light emitting diodes (LEDs), semiconductive or photoconductive devices, nonlinear optics, conversion of sunlight, formation of liquid crystals, etc. Wittig-Horner reactions of diphosphonates with mono- or dialdehydes or of dialdehydes with mono- or diphosphonates yielded the desired all-trans configured OPVs, which were designed for the complexation of metal cations. The Wittig-Horner reaction of dialdehyde 27a and diphosphonate 8a was in so far an exception as a small portion of an oligomer could be obtained which was the only soluble component in hot CHCl3.
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