Metal-acetylide addition to tetracyanoethylene |
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Authors: | Tristan A Reekie Jean-Paul Gisselbrecht Corinne Boudon Nils Trapp François Diederich |
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Institution: | 1. Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland;2. Laboratoire d’Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4, rue Blaise Pascal, 67081 Strasbourg, France |
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Abstract: | Two push-pull chromophores that have shown utility in the field of molecular electronics and non-linear optics are DDMEBT (1, 2-(4-dimethylamino)phenyl)-3-((4-(dimethylamino)phenyl)ethynyl)buta-1,3-diene-1,1,4,4-tetracarbonitrile) and TDMEE (2, 4-(4-dimethylamino)phenyl)but-1-en-3-yne-1,1,2-tricarbonitrile). Unfortunately, the methods reported for their synthesis give variable yields, use toxic solvents, and only provide small amounts of material. We report improved synthetic protocols, providing access to larger quantities of material. By investigating multiple metal-acetylides of 4-ethynyl-N,N-dimethylaniline and their subsequent addition to TCNE, we obtained various products depending on the identity of the metal ion. This led to the simple synthesis of push-pull chromophoric compounds. |
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Keywords: | Push-pull chromophores Tetracyanoethene Metal-acetylide additions Optoelectronics |
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