Squaraines have been known for many decades as very stable and versatile vis-NIR absorbing dyes. They have found applications for example as sensitizers in organic photovoltaics and photodetectors. The most common squaraine structure is the 1,3-regioisomer. Their 1,2-regioisomers are seldom mentioned and unanimously regarded as side products. A facile direct synthesis of 1,2-squaraines, highlighting the role played by reaction conditions and electronic factors, is described. The first electrochemical characterization of these dyes is also shown. © 2011 American Chemical Society.
Ronchi, E., Ruffo, R., Rizzato, S., Albinati, A., Beverina, L., Pagani, G. (2011). Regioselective Synthesis of 1,2- vs 1,3-Squaraines. ORGANIC LETTERS, 13(12), 3166-3169 [10.1021/ol201093t].
Regioselective Synthesis of 1,2- vs 1,3-Squaraines
RUFFO, RICCARDO;BEVERINA, LUCA;PAGANI, GIORGIO ALBERTO
2011
Abstract
Squaraines have been known for many decades as very stable and versatile vis-NIR absorbing dyes. They have found applications for example as sensitizers in organic photovoltaics and photodetectors. The most common squaraine structure is the 1,3-regioisomer. Their 1,2-regioisomers are seldom mentioned and unanimously regarded as side products. A facile direct synthesis of 1,2-squaraines, highlighting the role played by reaction conditions and electronic factors, is described. The first electrochemical characterization of these dyes is also shown. © 2011 American Chemical Society.
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