Polycyclic aromatic hydrocarbons (PAHs) have been attracting great attention from structural, environmental, and more recently molecular electronics perspectives. Their often planar or near-planar geometry and extended ?-delocalization render them appealing ?-? stacking building blocks which can be utilized to dictate controlled self-assembly processes. In addition, the potentially high charge mobility along the stacked PAH column may find applications in sensors, field effect transistors and photovoltaic devices. In this presentation, four alkoxy-substituted tribenzopentaphene (TBP) derivatives have been synthesized. When coated onto a pre-grown PDI nanofiber, all four compounds led to dramatic enhancement in the photocurrent response of the resulting nanofiber, with isopropoxyl TBP showing the best performance. The enhanced photocurrent is due to the facile photoinduced electron transfer from the TBP derivative to the excited PDI core which is facilitated by the well-matched HOMO/LUMO energy levels of the donor (TBP) and the acceptor (PDI) and by the short donor-acceptor distance due to the alky chain interdigitation. The lack of ?-? stacking of the donor TBP rings in isopropoxyl TBP helps minimize the charge recombination which accounts for its higher photocurrent response than the other TBP derivatives. Moreover solar cells fabricated from TBPs blended with PDI derivatives have also been studied.

Synthesis, self-assembly, and applications of tribenzopentaphene derivatives

245th National Meeting (2013)

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