Widely applicable metallacarborane reagents for φ-conjugated systems

Abstract

The compounds [N(CH3)4][3,3-Co(8-(p-C 6H4C2H3)-1,2-C2B 9H10)(1,2-C2B9H11)], [N(CH3)4][3,3-Co(8-(p-C6H4CHO)-1,2- C2B9H10)(1,2-C2B9H 11)], and [N(CH3)4][3,3-Co(8-(m-C 6H4CHO)-1,2-C2B9H 10)(1,2-C2B9H11)] were synthesized using an easy methodology, in very good yields and large quantities, which are important requisites to be employed as starting reagents. They have been fully characterized by elemental analysis, IR, NMR, and MALDI-TOF-MS, and the crystal structures of [N(CH3)4][3,3-Co(8-(p-C6H 4C2H3)-1,2-C2B9H 10)(1,2-C2B9H11)] and [N(CH 3)4][3,3-Co(8-(p-C6H4CHO)-1,2-C 2B9H10)(1,2-C2B9H 11)] were elucidated by single-crystal X-ray diffraction. These compounds, having terminal formyl and vinyl functional groups, are suitable platforms to involve the aromatic cobaltabisdicarbollide unit into extended φ-conjugated systems. It is expected that these synthons will facilitate the applicability of metallacarboranes in a wide variety of different fields, where φ-conjugated systems are needed to keep electronic communication. © 2014 American Chemical Society.