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Cyclobutadiene-C60Adducts: N-Type Materials for Organic Photovoltaic Cells with High VOC
- Source :
- Advanced Functional Materials. 23:3061-3069
- Publication Year :
- 2013
- Publisher :
- Wiley, 2013.
-
Abstract
- New tetraalkylcyclobutadiene–C60 adducts are developed via Diels–Alder cycloaddition of C60 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 C60 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 (VOC) in bulk heterojunction polymer solar cells. The tetramethylcyclobutadiene–C60 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 C60 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.
- Subjects :
- Fullerene
Materials science
Cyclobutene
Organic solar cell
Condensed Matter Physics
Photochemistry
Polymer solar cell
Electronic, Optical and Magnetic Materials
Biomaterials
chemistry.chemical_compound
chemistry
Electron affinity
Electrochemistry
Density functional theory
Cyclobutadiene
HOMO/LUMO
Subjects
Details
- ISSN :
- 1616301X
- Volume :
- 23
- Database :
- OpenAIRE
- Journal :
- Advanced Functional Materials
- Accession number :
- edsair.doi...........b5951ecb9e085d4b195a550fe3716640