New π-electron donor systems based on acenaphtho[1,2-b][1,4]dithiine
| Autor: | Alexander K. Lay, Martin R. Bryce, Andrei S. Batsanov, Judith A. K. Howard, Antony Chesney |
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| Rok vydání: | 1996 |
| Předmět: | |
| Zdroj: | J. Chem. Soc., Perkin Trans. 1. :2451-2459 |
| ISSN: | 1364-5463 0300-922X |
| DOI: | 10.1039/p19960002451 |
| Popis: | Syntheses of the acenaphtho[1,2-b][1,4]dithiine derivatives 12, 25 and 29 are reported. Cyclic voltammetric studies reveal that these compounds undergo reversible single-electron oxidations at < 1.0 V, vs. Ag/AgCl. Lithiation of compound 12 with BuLi (2 equiv.) followed by addition of either methyl iodide or ethyl chloroformate yielded the unstable ring-opened acetylene derivatives 22a and 22b, respectively. A new synthesis of 1,2-diselenine derivative 33 is reported. Compound 25 formed 1 : 1 charge-transfer complexes with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) and with 2,5-dibromo-TCNQ, both of which were electrical insulators. The X-ray crystal structures of compound 25, a charge-transfer complex 25:Br2TCNQ (1:1 stoichiometry) and compound 33 are reported. In the structure of 25:Br2TCNQ, molecules of 25 and Br2TCNQ form mixed stacks. The folding of the donor along the S ⋯ S vector in the complex is 17°(cf. 48° in pure 25) and the conformation of 25 is discussed in the light of previous studies on 1,4-dithiine derivatives. An interesting feature of the crystal structure of 33 is the formation of pseudo-dimers with two short intermolecular Se ⋯ Se contacts. |
| Databáze: | OpenAIRE |
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