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Synthesis and grafting properties of functionalized oligo( para ‐phenylene)s
Author(s) -
SiAhmed Lynda,
Nüesch Frank,
Zuppiroli Libero,
François Bernard
Publication year - 1998
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19980401)199:4<625::aid-macp625>3.0.co;2-5
Subject(s) - phenylene , polymer chemistry , arylene , monolayer , chemistry , oligomer , ethylene oxide , polymerization , materials science , polymer , organic chemistry , alkyl , biochemistry , aryl , copolymer
For the purpose of grafting conjugated molecules on metal or oxide electrodes (which is an essential step towards a new generation of reliable organic light emitting diodes), we have synthesized soluble oligocyclohexadienes (12 cyclic units) by anionic polymerization and functionalized them by carboxylic acids, thiol and siloxane. Aromatization of the oligomer to oligo( para ‐phenylene) (OPP) is carried out by dehydrogenation with chloranil. The adsorption of the carboxylic oligo( para ‐phenylene) derivatives on indium tin oxide powder is investigated by solution equilibration. In tetrahydrofuran (THF) an equilibrium constant of K = 21 500 1 · mol −1 and a maximum surface coverage ( N max ) of 4 μmol/m 2 are obtained by using the Langmuir equation. A characteristic area of 40 Å 2 per molecule is inferred from the surface density of absorbed oligo( para ‐phenylene), which indicates that a densely packed monolayer of vertically adsorbed molecules is formed.