A One-Step Synthesis of a Poly(iptycene) through an Unusual Diels−Alder Cyclization/Dechlorination of Tetrachloropentacene

A One-Step Synthesis of a Poly(iptycene) through an Unusual Diels−Alder Cyclization/Dechlorination of Tetrachloropentacene

We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels−Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600−900 °C). Theoretical ca...

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Veröffentlicht in:Journal of the American Chemical Society 2003-08, Vol.125 (34), p.10190-10191
Hauptverfasser: Perepichka, Dmitrii F, Bendikov, Michael, Meng, Hong, Wudl, Fred
Format: Artikel
Sprache:eng
Schlagworte:
Applied sciences
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polymers with particular structures
Preparation, kinetics, thermodynamics, mechanism and catalysts
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Zusammenfassung:We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels−Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600−900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja036193i