Synthesis, photophysical properties and applications of arylpyrene and dithienophenazine derivatives -

Abstract

The synthesis and full characterization of a series of pyrene-based compounds and their application in organic electronics owing to their blue-emitting properties is reported. The synthesis of these compounds was carried out from pyrene using different procedures including electrophilic aromatic substitution, reduction, oxidation, and Suzuki-Miyaura coupling reaction. The synthesis of a stable fluorescent sensor for anion detection based on a dithienophenazine core is also reported starting from an alpha-diketone and 1,2-benzene diamine. The synthesis involved tosylation, nitration, hydrogenation, keto-amino condensation, and Suzuki-Miyaura coupling reaction. In Chapter 2, we start by introducing pyrene and its properties. These included its chemical reactivity through electrophilic aromatic substitution, and its photophysical properties. Synthetic routes to reach different arylpyrene categories starting from unsubstituted pyrene are presented along with the photophysical advantages of the 1,3,6,8-tetraarylsubstitution. In this Chapter, the synthesis and full characterization of nine 1,3,6,8-tetraarylpyrene compounds (2.21-2.29) is described through three different synthetic procedures. The photophysical properties of these compounds in different environments including solid state will be discussed, in parallel to a discussion of their X-Ray structures and thermal properties. Based on this discussion their potential for being involved in organic electronic devices is evaluated. This is done in comparison to a reference compound (1,3,6,8-tetraphenylpyrene) and to pyrene itself, which illustrates the effect of different substituents on the properties of pyrene from a steric and an electronic point of view. In Chapter 3, a further step towards other arylpyrene categories (other than the 1,3,6,8-tetraarylpyrenes presented in Chapter 2) is made by the synthesis and characterization of new 2,7-diarylpyrene (3.1-3.3) and 2,7-diaryl-4,5,9,10-tetrahydropyrene (3.4-3.6) derivatives. The study focuses on their photophys