Cobaltacarborane–phthalocyanine conjugates: Syntheses and photophysical properties

Syntheses of two new cobaltacarborane–phthalocyanine conjugates, one anionic (Pc 6) and one zwitterionic (Pc 7), were accomplished via cyclotetramerization of the corresponding cobaltacarborane-substituted phthalonitriles (4 or 5) with excess phthalonitrile in quinoline. X-ray structures of two phthalonitrile precursors (2 and 3) were obtained and are discussed, and the absorption and emission properties of the two cobaltacarborane–phthalocyanine conjugates in several solvents were investigated. The anionic conjugate 6 exists mainly as a monomer in polar organic solvents and has fluorescence quantum yields in the region 0.2–0.3. The zwitterionic conjugate 7 aggregates in solution and displays lower quantum yields ∼0.1 in organic solvents.

Graphical abstractThe syntheses of two cobaltacarboranyl–phthalocyanines, one anionic and one zwitterionic, are described. While the anionic phthalocyanine exists mainly as a monomer in polar organic solvents and has fluorescence quantum yields in the region 0.2–0.3, the zwitterionic phthalocyanine aggregates in solution and displays lower quantum yields ∼0.1 in organic solvents.Figure optionsDownload full-size imageDownload as PowerPoint slide