In recent years, it is known that the porphyrin electronic system is susceptible to conjugative perturbation at the periphery. ^[1] So, the electronic and optical properties of porphyrin can be rationally tuned. Because of this, a variety of conjugated porphyrin arrays have been constructed over the last two decades. It is one strategy to link electron donors and electron acceptors together using π-conjugated molecular spacers to investigate photoinduced electron transfer processes on a molecular level. ^[2] The electronic properties of these molecules make them potentially useful in molecular photonics, optoelectronics, nanoscale application and in solar energy conversion. ^[1]

In this work, we report the synthesis and electronic properties of conjugated porphyrin dimer and monomers. All the porphyrins were synthesized using bromination, palladium catalyzed domino heck reaction followed by electrocyclization/dehydration strategy ^[3]and then imidation with coupling reagents.

Reference

[1] S. V. Kirner, D. Arteaga, C. Henkel, J. T. Margraf, N. Alegret, K. Ohkubo, B. Insuasty, A. Ortiz, N. Martı´n, L. Echegoyen, S. Fukuzumi, T. Clark and D. M. Guldi, Chem. Sci., 2015, 6, 5994–6007

[2] S. Fukuzumi, K. Ohkubo and T. Suenobu, Acc. Chem. Res., 2014, 47, 1455.

[3] Jinadasa, R. G. W.; Fang, Y.; Kumar, S.; Osinski, A. J.; Jiang, X.; Ziegler, C. J.; Kadish, K. M.; Wang, H. J. Org. Chem., 2015, 80 (24), 12076–12087