Synthesis And Properties Of Acceptor - Donor Conjugated Aromatic Macrocyclic Molecules Based On PDI

In recent years, organic photovoltaic materials have made rapid development in basic research and applications, they have become a more mature emerging interdisciplinary field. The organic photoelectric materials have been widely applied in the photovoltaic device, including organic light emitting diodes, organic solar cells, organic field effect transistors, organic biochemical sensors, as well as the organic nonlinear optical materials.Since the organic molecule than the inorganic material has strong advantages,such as low density、Low price and easy modification of the structure, in recent years it has been widespread attention in research and industry. chemists and materials scientists design and synthesis some specific organic π- conjugated system, and explore their application in optoelectronic functional areas, and as a feedback to guide molecular design. In 2008, the p-phenylene ring(cycloparaphenylenes, CPPs) compound has been first successful synthesized by Jasti, Bertozzi use of cis-1,4-dimethyl-2,5-cyclohexadiene molecules bridge. But the CCP don’t have strong absorption in the visible range, so its application is limited in the photovoltaic device. However, synthesis of this compound provides us with a synthetic strategy for cyclic compounds. And two different aromatic molecules such completely conjugated together to form a cyclic compound group that has not yet been synthesized, therefore, for this situation, we carried out the following two aspects of the research work.we designed and synthesized the conjugated macrocyclic molecules that incorporates two different aromatics. The donor is a bithiophene, and the acceptor is a perylene diimide derivative. The macrocycle formed has a persistent elliptiform cavity that is lined with the sulfur atoms of the thiophenes and the π-faces of the perylene diimide. Due to the linkage of the perylene diimide subunits,the macrocycles exist in both chiral and achiral forms. We separate the three stereoisomers using chiral high-performance liquid chromatography and study their interconversion. These unusual macrocycles are black in color with an absorption spectrum that spans the visible range. Density functional theory calculations reveal a photoinduced electron transfer from the bithiophene to the perylene diimide.Based on the previous research, we can see this new macrocyclic moleculehas a unique spectral absorption characteristics, with a strong absorption in the visible range, This makes the molecule with the possibility of application in solar photovoltaic devices. Because of this new conjugated aromatic macrocyclic molecules are synthesized for the first time. Although we understands its spatial structure and photoelectric properties, for this kind of PDI as receptors, other aromatics conjugated molecules as donor to form macrocyclic molecules, we have not studied them carefully. In order to understand the laws of such cyclic molecules、spatial characteristics and spectral characteristics, we synthesized several conjugated macrocyclic molecules and study their spatial structure and optical properties.