Colouring naphthalene diimides

Resumo

Naphthalene diimides have been explored in a wide variety of ways; They are a promising candidate for organic electronics, boasting the ability to form n-type semiconductor materials, the stability of their anions further aiding in this regard. Their electron poor aromatic core can be used in host guest chemistry to generate interlocked species. The ability to tune their electronic properties and how this could be manipulated to create photovoltaic devices is primarily focus of this thesis. A series of naphthalene diimides substituted at the core with morpholine moieties have been synthesized and their optical and electronic properties have been probed. Interestingly these species were found to not follow the typical trends for core substituted naphthalene diimides. Through further investigation it was revealed that this unexpected behavior was due to the conformation of core substituents, typically considered unimpactful. In addition to these species, more complex naphthalene diimide systems, core substituted with phenothiazine and phenoxazine, have been synthesized. By combination of the electron deficient naphthalene diimide with the electron rich phenothiazine and phenoxazine electron donor-acceptor species have been created. These species can be excited by visible light and upon excitation have the potential to generate a charge separated state, which could be used to generate current in a photovoltaic device. Finally a naphthalene diimide furnished with two BODIPY units was synthesized in an attempt to utilize it as the central rod of a rotaxane. The electronic properties of this rod species were also attempted to be modulated via thionation of the naphthalene diimide core. These species would be used to assess the viability of utilizing BODIPY as a light harvesting antenna for naphthalene diimide systems.