Synthesis of Fullerene Derivatives for Organic Solar Cells
Eneida Chesnut 1, Mingfeng Wang 2, Fred Wudl 2,3
Light
e-
Introduction & Research Goals
Organic solar cells are a promising renewable energy option,
characterized by two important features: they are low cost
and very flexible.
This project targets new electron-accepting materials for
organic solar cells. Specifically, it focuses on the synthesis
of fullerene-chromophore addends that show enhanced light
absorption in the UV-Vis range, which could potentially
augment the performance of organic solar devices.
1 Department of Chemical Engineering
3 Department of Chemistry & Biochemistry
2 Center for Polymers and Organic Solids (CPOS)
Acknowledgements
Ofelia Aguirre & Arica Lubin,
UCLEADS Program
Ali Mohebbi, Wudl’s Research
Group
• Avent et all, Synthesis and electrochemical behavior of [60]fullerene possessing
poly(arylacetylene) dendrimer addends, Royal Soc. of Chem. 2000, 1409 – 1413.
• Hummelen et all, Preparation and characterization of fulleroid and methanofullerene
derivatives, J. Org. Chem. 1995, 60, 532-538.• Adapted from www.lios.at
Contact Information:
Eneida Chesnut, email: [email protected]
Synthesis
NaOMe / pyridine
C60 / ODCB
Bucky-
EMD
Derivatives of emeraldicene (EMD), a green
organic chromophore presenting high
solubility in several organic solvents, were
reacted with [60]fullerenes and the products
were separated by column chromatography
and purified.
After a series of step-reactions, an
emeraldicene derivative was linked to a
specific position of a fullerene cage,
according to the following reaction:
a) MeOH / HCl
b) TsNHNH2 / MeOH
Characterization
Future research will investigate the application of these new chromophore-
attached fullerene derivatives in plastic solar cells.
Future Work
References
C60
Bucky-EMD
(calculated molecular weight =
1294 g/mol)
1294.2
C60
Bucky-EMD
EMDBO
