Iminium salts of omega-dithiafulvenylpolyenals: an easy entry to the corresponding aldehydes and doubly proaromatic nonlinear optic-phores |
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Authors: | Alías Silvia Andreu Raquel Blesa María Jesús Cerdán Miguel Angel Franco Santiago Garín Javier López Carolina Orduna Jesús Sanz Jorge Alicante Raquel Villacampa Belén Allain Magali |
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Institution: | Departamento de Química Orgánica, ICMA, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain. |
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Abstract: | A short, high-yielding route to omega-dithiafulvenylpolyenals (1) via the corresponding iminium salts (2) and starting from trimethyl-1,3-dithiolium tetrafluoroborate is reported. The Knoevenagel reactions of either 1 or 2 with isoxazolone-containing acceptors afford merocyanines 7 and 9, in a process that is often accompanied by a vinylene-shortening side reaction. Experimental and theoretical studies reveal that compounds 7 and 9, featuring two proaromatic end groups, are strongly polarized and show good second-order nonlinear optical responses. |
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