Thiophene–Bipyridine Appended Diketopyrrolopyrrole Ligands and Platinum(II) Complexes

Straightforward palladium(II) catalyzed direct cross-coupling reaction between decyl, (S)-2-methyl-butyl, and dodecyl N-substituted diketopyrrolopyrrole thiophene (DPPT), including a 3-methoxy-thiophene derivative, 6-bromo-2,2′-bipyridine afforded series of mono- bis-bipyridine substituted DPPT ligands 1–3. Complexation reactions with PtCl2(DMSO)2 provided ortho-metalated platinum(II) complexes 1-Pt 2-Pt, together the N^N^O complex 3d-Pt(N^N^O) resulted from O-Me activation intermediary 3d-Pt(N^N). The ligand 1b mononuclear 1a-Pt 1b-Pt have been structurally characterized by single crystal X-ray structure, evidencing establishment numerous intermolecular π–π interactions in solid state. Moreover, structure model DMTB-Pt(N^N^O) (DMTB = 3,4-dimethoxy-(2,2′-bipyridine)) chelating tridentate mode is clearly evidenced. chiral its do not show any CD signal solution, but they are active state bisignate bands low energy region, opposite sign complex, suggesting helical supramolecular arrangement dpp chromophore Photophysical investigations demonstrate that all fluorescent high quantum yields, while emission quenched for complexes, except partially 3d-Pt(N^N), very likely through an intersystem crossing mechanism promoted heavy metal. Density functional theory calculations support differences observed absorption properties ligands, ortho- non-ortho-metalated complexes. highly bipyridine reported herein open way toward multifunctional transition metal their use organic electronics.