Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction.

ABSTRACT: Ruthenium(0) catalyzed diol-diene benzannulation is applied to the conversion of oligo(p-phenylene vinylenes) 2a-c, 5 and 6 to alternating oligo(o,p-phenylenes) 10a-c, 11-13. Orthogonality with respect to conventional palladium catalyzed biaryl cross-coupling permits construction of p-bromo-terminated alternating oligo(o,p-phenylenes) 10b, 11-13, which can be engaged in Suzuki cross-coupling and Scholl oxidation. In this way, structurally homogeneous nanographenes 16a-f are prepared. Nanographene 16a, which incorporates 14 fused benzene rings, was characterized by single crystal X-ray diffraction. In a similar fashion, p-bromo-terminated oligo(p-phenylene ethane diol) 9

SUBMITTER: Kasun ZA 

PROVIDER: S-EPMC6194800 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature