[2.2.2]paracyclophane, a novel type of metal cation complexing agent (.pi.-prismand)

Abstract

A novel type of cryptation involving only the r-binding sites of the cavity [2.2.2]paracyclophane is evidenced through solubility and 'H NMR studies. The stability constant, in methanol, of the 1:l complex of [2.2.2]paracyclophane with silver triflate is approximately 100-fold higher than those of the usual r-charge-transfer complexes of arenes with silver cation. The well-defined, sharp-melting, crystalline, 1 : 1 complex has been isolated and characterized.

Novel potentiometric and optical silver ion-selective sensors with subnanomolar detection limits

“…Nitrogen as coordinating site has been used only in a few cases such as in pyridophanes [20] or tetraazacrown ethers [21]. Another group of chelators, applied more recently in polymeric membrane electrodes [9,[22][23][24], is based on π-electrons as the coordinating sites for Ag + (see, e.g., [25,26]). Such ionophores seem especially attractive for Ag + -sensors, since π-electrons do not significantly interact with most of the other ions.…”

Structure of the 1/1 complexes of [2.2.2]paracyclophanetriene and [2.2]paracyclophane with tetracyanoethylene

“…This work is part of a series of structural studies on paracyclophanes and their complexes with metal ions or electron-acceptor molecules such as tetracyanoethylene, TCNE (Pierre, Baret, Chautemps & Armand, 1981;Cohen-Addad, Baret, Chautemps & Pierre, 1983).…”

Structures cristallines du [2.2.2]paracyclophane (I) (C24H24) et de son complexe avec le perchlorate d'argent (II) (C24H24.AgClO4)

“…Les cyclophanes pr~sentent une cavit~ mol~culaire susceptible de complexer des ions m~talli-ques. Ainsi, l'insertion d'un atome de chrome dans la cavit~ de cyclophanes a 6t+ d+crite (Elschenbroich, M6ckel & Zenneck, 1978;Blank, Haenel, Koray, Weidenhammer & Ziegler, 1980) (Tabushi, Yamada, Oshida & Oda, 1971), l'6tude en solution de la formation d'un complexe de coordination entre (I) et l'ion Ag ÷ a 6t6 entreprise par certains d'entre nous (Pierre, Baret, Chautemps & Armand, 1981).…”