One-Pot And Stepwise Syntheses Of Two Novel Tricarbazolo Triazolophane Macrocycles
Fadler, Rachel E.
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Organic solar cells are much less efficient than their inorganic counterparts, and this inefficiency can be attributed to the inability to control the layout and orientation of electron-donor and electron-acceptor organic molecules at mixed heterojunctions. Consequently, organic photovoltaics could be improved by studying redox-active organic macrocycles that can self-assemble on surfaces. To this end, tricarbozolo triazolophane (tricarb) macrocycles were designed and synthesized from three redox-active, electron-donating carbazole subunits. The resulting planar, shape-persistent macrocycle was shown to organize into flower and honeycomb phases on graphite surfaces and to stack in an orderly manner off from the surface. However, the mechanisms that control the tricarb macrocycle’s assembly need to be further investigated. Presented here is the one-pot synthesis of C9 tricarbazolo triazolophane macrocycle (9) (three nonyl sidechains) and the new stepwise synthesis of C6, C6, C18 tricarbazolo triazolophane macrocycle (27) (two hexyl and one octadecyl sidechains). The successful syntheses of these macrocycles were confirmed by 1H NMR. In addition, the 1H NMR indicates that the alkyl chain lengths do not significantly impact the 1H NMR symmetry of the molecule. Furthermore, the C6, C6, C18 tricarb macrocycle’s (27) light orange color compared to the C9 tricarb macrocycles (9) beige color suggests that the C6, C6, C18 tricarb macrocycle (27) has greater conjugated character than the C9 tricarb macrocycle (9). The self-assembly of these tricarb macrocycles has yet to be studied on graphite, but these macrocycles’ are anticipated to increase our knowledge about how to tune or modify macrocycle assemblies.This SIP is confidential and not distributable. It is available to CACHE administrators only.