In this thesis, the syntheses and characterization of a series of cove-bridged saddle-shaped fenestrindane derivatives were reported. The structures of these novel molecules were established by various techniques, including NMR spectroscopy, mass spectrometry, X-ray crystallography, UV--vis spectroscopy, fluorescence spectroscopy and cyclic voltammetry.

Chapter 1 reviewed the growing research significance of nonplanar polyaromatic molecules, and the central aspects of the oxidative aromatic coupling reaction used in polyarene synthesis.

Chapter 2 outlined the definition, nomenclature and stereochemistry of fenestranes and fenestrindanes. The latter scaffold was emphasized in terms of structure, reactivity and unexplored respects.

Chapter 3 first described the research plan, and then disclosed the synthesis of the 1,4,9,12-tetraarylfenestrindane family which was well characterized. These molecules served to produce the target fenestrindane-based saddles by oxidative cyclization.

Chapter 4 discussed the oxidative cyclization outcomes of the prepared tetraarylfenestrindanes. The observed reactivity and selectivity were rationalized based on the arenium ion mechanism. The saddle topography of the cove-bridged fenestrindanes was established by X-ray crystallography. These derivatives were also examined in terms of their photophysical and electrochemical properties.

Chapter 5 concluded the thesis by pointing out the future perspectives founded on the reported new results.

This thesis demonstrated the unprecedented saddle-shaped structure of covebridged fenestrindane derivatives. The results formed the basis in furtherance of understanding the optoelectronic and supramolecular properties of larger fenestrindane-based pi-systems.