Cyclobutadiene–C[subscript 60] Adducts: N-Type Materials for Organic Photovoltaic Cells with High V[subscript OC]
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Author(s)
Han, Ggoch Ddeul
Collins, William R.
Andrew, Trisha Lionel
Bulovic, Vladimir
Swager, Timothy Manning
Date Issued
January 2013
Journal
Advanced Functional Materials
Publisher
Wiley Blackwell
Citation
Han, Ggoch Ddeul, William R. Collins, Trisha L. Andrew, Vladimir Bulovic, and Timothy M. Swager. “Cyclobutadiene-C60 Adducts: N-Type Materials for Organic Photovoltaic Cells with High VOC.” Advanced Functional Materials 23, no. 24 (June 25, 2013): 3061-3069.
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Author's final manuscript
Abstract
New tetraalkylcyclobutadiene–C[subscript 60] adducts are developed via Diels–Alder cycloaddition of C[subscript 60] with in situ generated cyclobutadienes. The cofacial π-orbital interactions between the fullerene orbitals and the cyclobutene are shown to decrease the electron affinity and thereby increase the lowest unoccupied molecular orbital (LUMO) energy level of C[subscript 60] significantly (ca. 100 and 300 meV for mono- and bisadducts, respectively). These variations in LUMO levels of fullerene can be used to generate higher open-circuit voltages (V[subscript OC]) in bulk heterojunction polymer solar cells. The tetramethylcyclobutadiene–C[subscript 60] monoadduct displays an open-circuit voltage (0.61 V) and a power conversion efficiency (2.49%) comparable to the widely used P3HT/PCBM (poly(3-hexylthiophene/([6,6]-phenyl-C61-butyric acid methyl ester) composite (0.58 V and 2.57%, respectively). The role of the cofacial π-orbital interactions between C[subscript 60] and the attached cyclobutene group was probed chemically by epoxidation of the cyclobutene moiety and theoretically through density functional theory calculations. The electrochemical, photophysical, and thermal properties of the newly synthesized fullerene derivatives support the proposed effect of functionalization on electron affinities and photovoltaic performance.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology. Department of Electrical Engineering and Computer Science
Massachusetts Institute of Technology. School of Engineering
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DOI of Published Version
https://doi.org/10.1002/adfm.201203251
