Benzobisoxazole Cruciforms and Guanosine Derivatives: Syntheses, Structural Analyses, and Optical Properties



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This dissertation presents two studies in supramolecular chemistry; one is the chemistry of benzobisoxazole cruciforms in which two linearly conjugated π systems meet at the unsaturated center, and the other is that of guanosine derivatives.

Chapter One. This chapter summarizes the previous work on molecular cruciforms: tetrakis(arylethynyl)benzenes, distyrylbis(arylethynyl)benzenes, tetrakis(aryl-vinyl)benzenes, and tetraethynylethenes.

Chapter Two. The synthesis, optical properties, and computational calculation of benzobisoxazole-based molecular cruciforms are presented. The potential use of donor/acceptor substituted cruciforms as sensors is also discussed, and optical response of cruciform compounds to different concentration of trifluoroacetic acid in the liquid state is presented.

Chapter Three. A method for the identification method of carboxylic acids, organoboronic acids, phenols, amines, ureas, and tetrabutylammonium salts is described using one of donor/acceptor substituted benzobisoxazole-cruciforms as the sensor.

Chapter Four. Structural study of benzobisoxazole cruciforms is presented: their solid state structures, obtained by X-ray crystallography, are presented.

Chapter Five. The synthesis and structural analysis of 8-arylethynyl substituted guanosine derivatives is presented. The structural effects of this substitution, in comparison to the previous work in guanosine chemistry, is also discussed.



Self-assembly, Benzobisoxazole, Cruciform molecules, Fluorophores, Sensors, Guanosine