Studies Towards Arene-fused Isoindolinones And AIE-active N,O-chelated Boron Complexes

In recent years,the discovery and research of multi-component reactions(MCR)has become a thriving field of chemical science.In many cases,multi-component processes,either directly or in combination with appropriate post-transformation,can be used to construct complex nitrogen-containing heterocyclic molecules,laying the foundation for the generation of biologically related combinatorial libraries.Organic and metal organic light-emitting compounds have attracted intense research interest due to their potential applications in organic light-emitting diodes(OLEDs),solar cells,laser dyes,photosensitizers,biomolecular markers,and molecular probes.Among various types of luminescent compounds,boron complexes based on N,O-bidentate ligands have received a particular attention because of their excellent optophysical properties,high thermal and photochemical stability and high fluorescence quantum yield.Accordingly,the content of this thesis is divided in two major parts.In the first part of this paper,we have summarized our efforts on the development of an efficient one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels-Alder/HCl-elimination cascade that provides a rapid access to the isoindolinone framework in a diversity-oriented fashion.The scope of the process has been investigated with respect to all four components and a comparison between the one-pot and sequential approaches is given.The possibility of a late-stage one-pot functionalization through the Suzuki coupling has been explored.The second part of this thesis focuses on the synthesis of organic luminescent material based on pyridine-enol and isoquinoline-enol boron complexes and their optical properties assessment.Specifically,we have prepared a series of N,O-chelated pyridine-enol boron complexes and studied the effect of substituents on their optical properties.In addition,wehave explored the possibility of functionalization of isoquinoline-enol boron complexes through the palladium-catalyzed couplings.Finally,the photoluminescence behavior of all newly synthesized complexes was studied in dichloromethane solution and in solid state.