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Issue 13, 2009
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Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; conformationally-controlled oligomers bearing electroactive groups

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Abstract

The design of polymers with repeating [C(NR2)2CH2CH2] units which may simultaneously provide conformational control and contain repeating electroactive centres is discussed; (NR2)2groups would be ideally provided by ortho-phenylenediamine derivatives, with 1,8-diaminonaphthalenes as alternatives. Oligomers containing 1,8-bis(methylamino)naphthalenes, up to the hexamer, were obtained by condensation of oligomers of CH3[COCH2CH2]nCOCH3 with 1,8-bis(methylamino)naphthalene, but attempts to prepare related oligomers from 1,2-bis(alkylamino)benzenes were unsuccessful, as only terminal ketone groups could be converted to aminals. Evidence for a strong preference for all-anti conformations of the main chain in the naphthalenediamine oligomers is provided by ring current effects on 1H NMR shifts, and by X-ray structures, which also provide evidence of intercalation in the solid state. Electrochemical studies of these oligomers show irreversible oxidation of oligomers in solution, but oxidation of longer oligomers leads to the deposition of a reddish-pink insoluble material which shows two reversible oxidation waves. Possible interpretation of these results is discussed.

Graphical abstract: Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; conformationally-controlled oligomers bearing electroactive groups

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Publication details

The article was received on 20 Jan 2009, accepted on 01 Apr 2009 and first published on 08 May 2009


Article type: Paper
DOI: 10.1039/B901060B
Org. Biomol. Chem., 2009,7, 2704-2715

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    Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; conformationally-controlled oligomers bearing electroactive groups

    R. W. Alder, N. P. Hyland, J. C. Jeffery, T. Riis-Johannessen and D. J. Riley, Org. Biomol. Chem., 2009, 7, 2704
    DOI: 10.1039/B901060B

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