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DOI: 10.1039/A604111F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 827-832

The synthesis and non-linear optical properties of (N-alkylpyrrol-2-yl)squaraine derivatives. Part 1

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Daniel E. Lynch, Uwe Geissler, Ian R. Peterson, Mathias Floersheimer, Roland Terbrack, Li Feng Chi, Harald Fuchs, Nicolas J. Calos, Barry Wood, Colin H. L. Kennard and G. John Langley

Abstract

The synthesis of a soluble poly(pyrrolylsquaraine) was achieved by N-alkylation of the pyrrole nucleus with 1-bromooctadecane and subsequent condensation with squaric acid. Bis(1-octadecylpyrrol-2-yl)- squaraine was also produced and found to exist in a variety of inseparable isomeric forms. When deposited as Langmuir–Blodgett monolayers on hydrophilic substrates, these dyes exhibit second harmonic generation (SHG) with deff = 0.5 ± 0.1 pm V-1 for both. For comparison, bis(3,5-dimethyl-1-octadecylpyrrol-2-yl)squaraine was synthesised and revealed a higher SHG activity of deff = 1.8 ± 0.2 pm V-1. Poly(1-octadecylpyrrolylsquaraine) is the first alternating donor–acceptor polymer to give SHG.

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