Expanding the Realm of Furan-Based Conducting Polymers through Conjugation with 1,6-Methano[10]annulene

The synthesis of a new bisfuranyl monomer, 2,7-bis(2-furanyl)-1,6-methano[10]annulene, is presented. Its properties and those of its polymer, synthesized via electropolymerization, are compared to those of the known furan−arene−furan monomers and their respective polymers. Investigation using UV−vis...

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Bibliographic Details
Published in:Macromolecules 2009-07, Vol.42 (13), p.4449-4455
Main Authors: Peart, Patricia A, Tovar, John D
Format: Article
Language:English
Subjects:
Applied sciences
Exact sciences and technology
Physicochemistry of polymers
Polymerization
Polymers and radiations
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Summary:The synthesis of a new bisfuranyl monomer, 2,7-bis(2-furanyl)-1,6-methano[10]annulene, is presented. Its properties and those of its polymer, synthesized via electropolymerization, are compared to those of the known furan−arene−furan monomers and their respective polymers. Investigation using UV−vis spectroscopy, cyclic voltammetry, and spectroelectrochemistry indicated that the 1,6-methano[10]annulene copolymer has properties rivaling those of the copolymers containing traditional aromatic cores. These results are rationalized in conjunction with DFT calculations, and they further the premise that 1,6-methano[10]annulene can be viewed as a viable building block for advanced π-conjugated electronic materials.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma9006494