Synthesis of Oligomeric Benzoporphyrins Via Imidation

Tuesday, 30 May 2017
Grand Ballroom (Hilton New Orleans Riverside)
Y. Hu, R. G. W. Jinadasa (University of North Texas), and H. Wang (Miami University)
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.


[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