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

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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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