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Extended conjugation in stilbenoid squaraines

Abstract Squaraines, two-fold condensation products in 1,3-position of squaric acid, represent dyes or pigments of high actuality. After their first boom in electrophotography diverse applications are presently studied in a wide area of research, which reaches from electrooptical materials to biosensors and compounds used in photodynamic therapy. Absorption and/or emission ranges in the NIR are mandatory for many of these techniques. The present article deals with stilbenoid squaraines, which feature an extended conjugation in their biradicaloid D-π-A-π-D structure. Due to the charge-transfer character of the excitation, boundaries are set for the optimal length of the conjugation. The absorption maxima of the stilbenoid squaraines and their aggregates are lying in chloroform as a solvent between 600 and 1000 nm. In the solid state panchromatic absorptions can be observed, which reach far into the NIR region. The facile preparation of squaraines bearing stilbene building blocks in one or two of their arms and moreover the easy access to dyes with multiple squaraine units fixed to stilbenoid scaffolds promise a wide palette of further applications in materials science.