There has been a notable surge of interest in the identification and optimization of materials that yield efficient organic photovoltaic solar cells. One synthetic approach for increasing the band gap in C60 derivatives is the addition of multiple adducts to C60. Multiple additions to C60 disrupt C60's pi-conjugated network, affording a higher LUMO by virtue of a larger band gap. However, syntheses that exploit multi-additions to C60 can be problematic due to the multiplicity of resulting C60 isomers. One attractive approach towards limiting isomer formation in C60 multiadducts is via tether directed bis-functionalization. Here we present the synthesis of a series of tether directed C60 bis adducts. The tethers were fashioned using DCC couplings derived from a combination of benzoyl propionic or benzoyl butyric acid with a sterically restrictive 1,2 or 1,3 or 1,4 Dimethanol Benzene linker. This tethered synthon will be used to bis functionalize C60, raising its LUMO.

Tether directed remote functionalization of C60

245th National Meeting (2013)

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