Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates.

This work describes the synthesis of PCBM ([6,6]-phenyl-C-butyric acid methyl ester) derivatives and other methanofullerene derivatives via generation of fullerene radical anions under photoirradiation and controlled by photoswitching, without preparation, a strong reducing agent, or precise control of the reaction conditions.

Regioselectivity enhancement in synthesis of [70]fullerene derivatives by introduction of a branched structure.

Regio-purity in [70]fullerene derivatives is of great importance to improve the power conversion efficiencies of organic photovoltaics. We found that the introduction of a branched structure to [70]PCBM enhanced the yield of α-isomers. The effect of the steric group in the reaction mechanism was theoretically investigated and a difference in the activation energies within specific pathways was revealed.

Controlling the Polarity of Fullerene Derivatives to Optimize Nanomorphology in Blend Films.

Developing a design strategy to establish the compatibility of acceptor materials with donor materials is important for the rational development of organic solar cells. We synthesized 2,6-dimethoxyphenyl methanofullerene derivatives to realize an enhanced open-circuit voltage, and we investigated polarities and their effects on the film morphology of the active layer. The polarities of the synthesized fullerene derivatives were affected significantly by the presence of functional groups, such as methoxy, ether, and ester groups.

Design of fullerene derivatives for stabilizing LUMO energy using donor groups placed in spatial proximity to the C60 cage.

A series of arylated dihydrofullerene derivatives were synthesized to elucidate the effective design of fullerene derivatives for enhancing the performance of organic photovoltaics. The LUMO energy of the fullerenes was estimated by the first reduction potential and theoretical calculations. The results showed that the methoxy groups substituted at spatial proximity to the fullerene core offered significant stabilization of the LUMO level.

Synthesis of thienyl analogues of PCBM and investigation of morphology of mixtures in P3HT.

Novel [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) analogues containing benzo[b]thiophene (3a, 3b) and thieno[3,2-b]thiophene (3c, 3d) were synthesized and characterized. The morphology of the thin films prepared from the mixtures of these methanofullerenes with regioregular poly(3-hexylthiophene) (P3HT) was investigated by AFM measurement and UV-Vis absorption spectroscopy. A solubility test of these methanofullerenes was performed by using dichloromethane as a solvent.