Molecular saddles, 2: 2,6-Dialkoxy-9,10-bis(1,3-dithiol-2-ylidene)-9,10- dihydroanthracene derivatives: Synthesis, electrochemistry and X-ray crystal structures of neutral and dication species

Martin R. Bryce, Terry Finn, Andrei S. Batsanov, Ritu Kataky, Judith A.K. Howard, Svetlana B. Lyubchik

Resultado de pesquisarevisão de pares

25 Citações (Scopus)

Resumo

The synthesis of 2,6-dialkoxy-9,10-bis(1,3-dithiol-2-ylidene)9,10- dihydroanthracene derivatives 15 and 16 is described. Solution electrochemistry shows that 15 and 16 display three redox waves, representing the sequential formation of the dication, radical trication and tetracation species in an E(q)E(q)E(q) process. The X-ray crystal structures of neutral compounds 15 and 16 and the charge transfer complex (15)2+(TCNQ-·)2. 2MeCN are reported. The neutral molecules adopt a saddle-like conformation; the bis(1,3-dithiole)benzoquinone system is U-shaped through an accumulating bend' comprising the boat conformation of the central (quinonoid) ring and folding of both 1,3-dithiole rings. In the complex (15)2+(TCNQ-·)2. 2MeCN the anthracene system is planar and aromatic; the dithiolium cations form a dihedral angle of 78°with the anthracene plane. The TCNQ anion radicals form a stack of dimers with interplanar separations of 3.15 Å within a dimer and 3.50 Å between the dimers. The structure contains unusually short intermolecular S···N contacts [2.865(3) Å].

Idioma originalInglês
Páginas (de-até)1199-1205
Número de páginas7
RevistaEuropean Journal of Organic Chemistry
Número de emissão7
DOIs
Estado da publicaçãoPublicadas - abr. 2000
Publicado externamenteSim

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