Synthesis Characterization and Optical Porperties of a Syano functionalized 4,5,9,10 Tetraaryl 6 Dioxapyrene

摘要

5,l O-Di(4-cyanophenyl) -4,9-di(4-methylphenyl)- 1,6-dioxapyrene ( CN-diox) , a symmetrically substituted 4,5,9,1O-tetraaryldioxapyrene, was synthesized in seven steps from 1,4-dihydroxynaphthalene. The synthetic methodology incorporated a base-catalyzed ringclosure process followed by dehydration to introduce the first tetraaryl- 1,6-dioxapyrene. Crystal structure and electrochemical analysis were performed to directly compare the properties of CNdiox to previously reported dioxapyrene derivatives, specifically 1,6-dioxapyrene (Diox) and 4,9- diethyl-2,7-dimethyl- 1,6-dioxapyrene (Alkyl-diox). Optical spectroscopy studies were performed to evaluate the potential of the 1,6-dioxapyrenes as fluorescent probes.