Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole

Abstract

Novel meso-meso directly linked porphyrin hybrids were successfully targeted and synthesized, with porphyrin units linked with dipyrrin, bidipyrrin or thiacorrole, expanding the ranges of dipyrrin derivatives and showing diverse metal coordinations and further influencing the chemical shift of pyrrole units. The porphyrinyl dipyrrin nickel complex 3 was successfully obtained in a high yield by the oxidation of porphyrinyl dipyrromethane 2 and subsequent coordination. Further oxidative coupling reactions of 3 afforded por-bidipyrrin-por hybrid 4. Interestingly, an unexpected methoxy por-bidipyrrin-por hybrid 6 was generated by treating 4 with FeCl3 in CH2Cl2/MeOH and subsequent coordination. In addition to open chain hybrids, an aromatic scaffold hybrid por-thiacorrole-por 8 was synthesized by treating porphyrinyl dibromo-dipyrrin nickel complex 7 with Na2S·9H2O. A series of porphyrin hybrids offers a new approach for π-conjugated molecules.

Multifaceted Applications of Luminescent Metalloporphyrin Derivatives: Fluorescence Turn-On Sensing of Nicotine and Antimicrobial Activity

“…A doublet at 10.0 ppm was observed presumably due to the hydrogens attached to the meso carbon centers (referred as a) (Figure ). The peak experienced significant broadening as well as slight upfield shifts upon interaction with nicotine. Again, in the aliphatic region, the peaks (f, g) for aliphatic residue at 3.61 ppm were also downfield-shifted and become broad with the interaction of nicotine.…”

Heterocorroles: corrole analogues containing heteroatom(s) in the core or at a meso-position

“…Kong and co-workers 20 reported the synthesis of a meso – meso linked porphyrin–corrole hybrid (triad) in which 10-thiacorrole was flanked by two porphyrin units ( Scheme 13 ). Porphyrinyl dipyrromethane 41 upon consecutive bromination, 2,3-dichloro-5,6-dicyano-benzoquinone (DDQ) oxidation and treatment with Ni( ii ) salt resulted in an unstable intermediate 42, which on treatment with Na 2 S·9H 2 O yielded triad 43 in 41% yield.…”