Trifluoromethyl/Perfluoroalkyl Corannulenes: Directed Synthesis And Photophysical Characterization

Buckyball is a fragment of fullerene,or the end cap of a single-walled carbon nanotube.They are considered to be building blocks of many important elements.Corannulene is a bowl-shaped molecule composed of five fused benzenoid rings that has C_5v symmetry,which could also regard as a hydrogen-terminated fragment of C₆₀.Due to its curved aromatic structure,corannulene possesses unique electron accepting ability,and displays extensive application prospects in numerous areas such as material chemistry,molecular electronics and photochemistry.With the discovery of an efficient method to prepare corannulene in kilogram quantities,it is relatively easy to obtain many corannulene derivatives from this parent compound.Given the existence of robust procedures to make halocorannulenes and corannuleneboronates?including mono-and penta-substituted corannulenes?,it became ideal to prepare other functionalized derivatives based on these precursors.This thesis presents a novel copper-mediated synthetic approach for the synthesis of perfluoroalkyl substituted corannulene derivatives.The reactions are carried out under mild conditions and deliver a good yield in gram-scale.This method also does not require expensive trifluoromethyl reagents.Other perfluoroalkyl groups such as perfluoroethyl and perfluorooctyl group can also be introduced onto corannulene through this method.This mild and selective methodology enables production of sufficient material to conduct further electrochemical and photophysical measures on a cognate series of these perfluoroalkylated corannulene derivatives.The electrochemical measurements reproduce well previous measurements.The optical measurements display a constant set of electronic transitions across the series.