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.
Regioselective Synthesis of 1,2- vs 1,3-Squaraines / E. Ronchi, R. Ruffo, S. Rizzato, A. Albinati, L. Beverina, G.A. Pagani. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 2011:12(2011), pp. 3166-3169. [10.1021/ol201093t]
Regioselective Synthesis of 1,2- vs 1,3-Squaraines
S. Rizzato;A. Albinati;
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.
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