Soluble High Molecular Weight Poly(p-phenylene) as a Charge-Transfer Complex

Soluble high molecular weight poly(p-phenylene) (PPP), in the form of a charge-transfer complex, was synthesized by complete dehydrogenation of poly(1,3-cyclohexadiene) (PCHD) with excess tetrachloro-1,2-(o)-benzoquinone (TOQ). The yield of the PPP-TOQ complex increased as the molecular weight of th...

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Bibliographic Details
Published inMacromolecules Vol. 42; no. 6; pp. 1964 - 1969
Main Authors Natori, Itaru, Natori, Shizue, Ogino, Kenji
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 24.03.2009
Subjects
Applied sciences
Chemical modifications
Chemical reactions and properties
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Benzoquinone derivatives
Photoluminescence
Phenylene polymer
Experimental study
Organic solution
Cyclodiene polymer
Conjugated polymer
Chemical modification
Chlorine Organic compounds
Preparation
Soluble compound
Charge transfer compound
Aromatic dehydrogenation
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Summary:Soluble high molecular weight poly(p-phenylene) (PPP), in the form of a charge-transfer complex, was synthesized by complete dehydrogenation of poly(1,3-cyclohexadiene) (PCHD) with excess tetrachloro-1,2-(o)-benzoquinone (TOQ). The yield of the PPP-TOQ complex increased as the molecular weight of the original PCHD increased. The addition of TOQ to the PPP polymer chain occurred mainly at the 1,4-phenylene (Ph) units. The PPP-TOQ complex showed good solubility in tetrahydrofuran; the solubility was not limited by the length of the 1,4-Ph sequence. The formation of the PPP-TOQ complex effectively suppressed crystallization of PPP due to the decrease in π−π intermolecular interactions in the PPP molecules, and had a significant effect on π-orbital conjugation in PPP.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma802561j