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Practical Synthesis of Vinyl‐Substituted p ‐Phenylenevinylene Oligomers and Their Triethoxysilyl Derivatives
Author(s) -
Sugiono Erli,
Metzroth Thorsten,
Detert Heiner
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(20010430)343:4<351::aid-adsc351>3.0.co;2-2
Subject(s) - chemistry , silanes , chromophore , conjugated system , metathesis , dispersity , polymer chemistry , polymer , grubbs' catalyst , heck reaction , organic chemistry , catalysis , polymerization , silane , palladium
Luminescent semiconducting organic compounds are widely used as active layers in electro‐optical devices. Apart from conjugated polymers, monodisperse oligomers also represent attractive materials. The synthesis of stilbenoid oligomers with polymerizable end groups is presented. Oligo(phenylenevinylene)s with terminal vinyl groups 17 – 19 are prepared in good yields by Horner–Emmons olefinations or by the Heck reaction of the iodo‐substituted oligomers 15 , 16 with compressed ethene. Triethoxysilyl groups can be linked via rigid 1,2‐vinylene units to the chromophores 26 – 30 , either in the direct reaction of 14 , 24 with silanes 21 , 22 or by cross‐metathesis of 17 – 19 with the vinylsilanes 21 , 22 using Grubbs catalyst.