Solid-state complexes of quinoxaline- and phenazine-N,N′-dioxide donors with tetracyanoethylene. Crystal engineering via donor-acceptor interactions

• Published in: Tetrahedron letters Vol. 38; no. 44; pp. 7665 - 7668
• Main Authors: Greer, Melinda L., Duncan, Joseph R., Duff, Janice L., Blackstock, Silas C.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 03.11.1997
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(97)10089-2

2,3-Dimethylquinoxaline-N,N′-dioxide (DMQDO) and phenazine-N,N′-dioxide (PDO) bind to tetracyanoethylene (TCNE) in solution, with complexation constants of 4.8(7) and 1.2(7) M −1, respectively in CH 2Cl 2. Crystallization of the mixtures affords two-component solids which contain weakly bound one-dimensional donor-acceptor arrays. The DA interactions create DA ladder domains in the (DMQDO) 2TCNE solid and single-stranded DA chains in the (PDO)TCNE crystal. The interactions of 2,3-dimethylquinoxaline-N,N′-dioxide and phenazine-N,N′-dioxide with tetracyanoethylene (TCNE) are investigated. X-ray crystal structures of the complexes show donor-acceptor interactions between the donor oxygens and the olefinic carbons of TCNE which result in one-dimensional DA ladder and chain formations in the complex solids.