title: Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties.
abstract: The syntheses of three new [3]radialenes - hexakis(3,5-dimethylpyrazolyl)-, hexakis(3-cyanophenyl)-, and hexakis(3,4-dicyanophenyl)[3]radialene (1-3) - are reported. Compound 3 is obtained in five steps with an excellent yield of 76% in the key step. Compared to that, the respective steps of the syntheses of 1 and 2 result in lower yields. All compounds adopt a double bladed propeller conformation in solution. Compound 3 is considerably more electron deficient than previously reported hexaaryl[3]radialenes, with reduction potentials of -0.06 and -0.45 V in CH(2)Cl(2). The compounds mostly display red fluorescence with large Stokes shifts.
authors.affiliation: School of Chemistry & Physics, The University of Adelaide, Adelaide, SA 5005, Australia.
authors.forename: Antonio
authors.initials: A
authors.lastname: Avellaneda
authors.forename: Courtney A
authors.initials: CA
authors.lastname: Hollis
authors.forename: Xin
authors.initials: X
authors.lastname: He
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Sumby