H. Wang, L. Kerr, R. G. W. Jinadasa, B. Li, B. Schmitz, A. Matus, and Y. Hu (Miami University)
Significant progress has been made on dye-sensitized solar cells sensitized by push-pull porphyrins in recent years.
1-3 Through installing push-pull groups at porphyrin
meso-positions, exceptionally high power conversion efficiencies have been achieved.
4, 5 In this work, we present the recent progress on synthesis and characterization of new classes of functionalized
pi-extended porphyrins, and their application as sensitized for dye-sensitized solar cells. We show that through installing push-pull groups at the porphyrin
beta-positions, both the UV-Vis absorption bands and fluorescence emission bands are much red-shifted and broadened relative to those of the porphyrins bearing no push-pull groups. These porphyrins show moderate to high power conversion efficiencies. In addition, anchoring group effects will also be discussed in this presentation. The design and synthesis of these organic materials take advantage of the chemistry of bromoporphyrins
6-9 and a palladium (0) catalyzed cascade reaction developed in the Wang group.
10 The electronic and optical properties of these
p-extended porphyrins were measured using UV-Vis spectroscopy, life-time and steady state fluorescence spectroscopy, and cyclic voltammetry. DFT calculations were also performed for these porphyrins.
Reference
1. T. Higashino and H. Imahori, Dalton Trans., 2015, 44, 448-463.
2. M. Urbani, M. Gratzel, M. K. Nazeeruddin and T. Torres, Chem. Rev., 2014, 114, 12330-12396.
3. L. L. Li and E. W. Diau, Chem. Soc. Rev., 2013, 42, 291-304.
4. A. Yella, H.-W. Lee, H. N. Tsao, C. Yi, A. K. Chandiran, M. K. Nazeeruddin, E. W.-G. Diau, C.-Y. Yeh, S. M. Zakeeruddin and M. Grätzel, Science, 2011, 334, 629-634.
5. S. Mathew, A. Yella, P. Gao, R. Humphry-Baker, B. F. Curchod, N. Ashari-Astani, I. Tavernelli, U. Rothlisberger, M. K. Nazeeruddin and M. Gratzel, Nat. Chem., 2014, 6, 242-247.
6. L. Jaquinod, R. G. Khoury, K. M. Shea and K. M. Smith, Tetrahedron, 1999, 55, 13151–13158.
7. L. Jaquinod, R. G. Khoury, K. M. Shea and K. M. Smith, Tetrahedron, 1999, 55, 13151-13158.
8. O. Siri and K. M. Smith, Tetrahedron Lett., 2003, 44, 6103-6105.
9. M. J. Crossley, P. L. Burn, S. S. Chew, F. B. Cuttance and I. A. Newsom, J. Chem. Soc., Chem. Commun, 1991, 1564-1566.
10. R. Deshpande, L. Jiang, G. Schmidt, J. Rakovan, X. Wang, K. Wheeler and H. Wang, Org. Lett., 2009, 11, 4251-4253.