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

Lynch, Daniel E., Geissler, Uwe, Peterson, Ian R., Floersheimer, Mathias, Terbrack, Roland, Chi, Li Feng, Fuchs, Harald, Calos, Nicolas J., Wood, Barry, Kennard, Colin H.L. and Langley, G. John (1997) The synthesis and non-linear optical properties of (N-alkylpyrrol-2-yl)squaraine derivatives. Part 1. Journal of the Chemical Society. Perkin Transactions 2, (4), 827-832. (doi:10.1039/a604111f).

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 d_eff = 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 d_eff = 1.8 ± 0.2 pm V^-1. Poly(1-octadecylpyrrolylsquaraine) is the first alternating donor-acceptor polymer to give SHG.

This record has no associated files available for download.

Contributors

Author: G. John Langley

Download statistics