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To examine the influence of molecular planarity and conjugation effects on physicochemical properties of porphyrin π-system through  meso -thienyl ring, a new class of anthracene and pyrene appended  trans- ThPPZn(II)-An and  trans- ThPPZn(II)-Py porphyrins have been synthesized. An efficient and facile methodology is adopted for the synthesis of  trans -5NThPPM and  trans- 5AThPPM (where M = H 2 , Cu(II), Ni(II), Zn(II)) porphyrins from 5(5-nitro-2-thienyl)dipyrromethane. The  1 H NMR spectra of the synthesized porphyrins showed two signals of equal intensity corresponding to the pyrrolyl β-protons, which evidenced the structure of  trans- isomers. Electronic spectroscopy and cyclic voltammetry explain the near co-planarity of the thien-2-yl group with the central porphyrin π-system which can influence the electron delocalization on these molecules. The present study reveals the existence of resonance interaction between porphyrin core and anthracene/pyrene moiety in their thien-2-yl bridged conjugates.

polycyclic aromatic compounds

Investigation on the Role of Molecular Planarity and Conjugation Effects on Physicochemical Properties of Anthracene and Pyrene Appended  meso -5,15-Bis(Thien-2-yl)-10,20-Diphenylporphyrin Triads