Symmetry-Breaking Charge Transfer in a Zinc Chlorodipyrrin Acceptor for High Open Circuit Voltage Organic Photovoltaics

Andrew N. Bartynski, Mark Gruber, Saptaparna Das, Sylvie Rangan, Sonya Mollinger, Cong Trinh, Stephen E. Bradforth, Koen Vandewal, Alberto Salleo, Robert A. Bartynski, Wolfgang Bruetting, Mark E. Thompson

Research output: Contribution to journalArticlepeer-review

73 Scopus citations


© 2015 American Chemical Society. Low open-circuit voltages significantly limit the power conversion efficiency of organic photovoltaic devices. Typical strategies to enhance the open-circuit voltage involve tuning the HOMO and LUMO positions of the donor (D) and acceptor (A), respectively, to increase the interfacial energy gap or to tailor the donor or acceptor structure at the D/A interface. Here, we present an alternative approach to improve the open-circuit voltage through the use of a zinc chlorodipyrrin, ZCl [bis(dodecachloro-5-mesityldipyrrinato)zinc], as an acceptor, which undergoes symmetry-breaking charge transfer (CT) at the donor/acceptor interface. DBP/ZCl cells exhibit open-circuit voltages of 1.33 V compared to 0.88 V for analogous tetraphenyldibenzoperyflanthrene (DBP)/C60-based devices. Charge transfer state energies measured by Fourier-transform photocurrent spectroscopy and electroluminescence show that C60 forms a CT state of 1.45 ± 0.05 eV in a DBP/C60-based organic photovoltaic device, while ZCl as acceptor gives a CT state energy of 1.70 ± 0.05 eV in the corresponding device structure. In the ZCl device this results in an energetic loss between ECT and qVOC of 0.37 eV, substantially less than the 0.6 eV typically observed for organic systems and equal to the recombination losses seen in high-efficiency Si and GaAs devices. The substantial increase in open-circuit voltage and reduction in recombination losses for devices utilizing ZCl demonstrate the great promise of symmetry-breaking charge transfer in organic photovoltaic devices.
Original languageEnglish (US)
Pages (from-to)5397-5405
Number of pages9
JournalJournal of the American Chemical Society
Issue number16
StatePublished - Apr 14 2015
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The authors would like to acknowledge the following agencies for funding of this work: The Department of Energy, Office of Basic Energy Sciences as part of Energy Frontier Research Center program, the Center for Energy Nanoscience (DE-SC0001013, A.N.B., C.T., S.D., S.E.B.), NanoFlex Power Corp. (M.E.T.). King Abdullah University of Science and Technology (KAUST), through the Center for Molecular Photovoltaics (CAMP) is gratefully acknowledged. S.M. acknowledges support from a Stanford Graduate Fellowship. The authors also thank Bavaria California Technology Center (BaCaTeC) (M.G, W.B.). R.A.B. and S.R. were supported through grant NSF-CHE 1213727.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.


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