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The condensation of MeP(SiMe 3 ) 2 with a series of 5-substituted isophthaloyl chlorides (5-R'C 6 H 3 -2,6-{C(O)Cl} 2 ) affords the diphosphametacyclophanes m -{-C(O)-C 6 H 3 -5-R'-(C(O)PMe)} 2 (R' = I, Me,    Bu, Ph, and p -NCC 6 H 4 ); the analogues m -{-C(O)-C 5 H 3 N-(C(O)PMe)} 2 and m -{-C(O)-C 6 H 4 -(C(O)PPh)} 2 are similarly obtained in preference to higher oligomers, in contrast to precedent reports. The cyclophanes all adopt butterfly-like conformations in the solid state with the P-organyl substituents adopting mutually exo arrangements. Structural and computational data suggest the nature of the 5-R substituent is key in directing the inter-ring angle and the extent of LUMO stabilization about the diketophophanyl scaffold. The latter is substantiated by UV/vis spectroscopy and cyclic voltammetry, which demonstrate these cyclophanes to be appreciably comparable to the diketophosphanyl systems commonly explored in the context of organic electronic materials; intriguingly, the distinct dikeophosphanyl moieties within the macrocycles appear effectively "insulated" by the macrocycle geometry, rather than acting as a through-conjugate.

Diphosphametacyclophanes: Structural and Electronic Influences of Substituent Variation within a Family of Bis(diketophosphanyl) Macrocycles