title: Twisted, Z-shaped perylene bisimide.
abstract: The first derivative of a new class of perylene bisimide chromophores, N,N'-bis(octyl)-3,9-bis(phenyl)perylene-1,2,7,8-tetracarboxyl bisimide, 1, has been synthesized and its fundamental photophysical and electrochemical properties assessed. The extended, Z-shaped structure was achieved by use of the classic photoenolization of an o-methylbenzophenone analogue, 1,5-dibenzoyl-9,10-dihydroanthracene, and in situ Diels-Alder trapping of the resulting o-xylylenol intermediates with N-octylmaleimide. Subsequent dehydration and aromatization of the resulting bisadduct afforded 1. In dichloromethane, bisimide 1 has an absorption lambdamax at 491 nm (epsilon = 29,600 M-1 cm-1), a fluorescence lambdamax at 517 nm with a high quantum yield (Phi = 0.70), and a single-exponential fluorescence decay (tau = 5.01 ns). Pure crystals of 1 have red emission, suggesting exciplex formation in the solid state. X-ray crystallographic analysis of 1 revealed significant twisting of its perylene core.
authors.affiliation: Polymers Branch, Materials and Structures Division, NASA Glenn Research Center, 21000 Brookpark Road, Cleveland, Ohio 44135, USA.
authors.forename: Faysal
authors.initials: F
authors.lastname: Ilhan
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Tyson
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Stasko
authors.forename: Kristin
authors.initials: K
authors.lastname: Kirschbaum
authors.forename: Michael A
authors.initials: MA
authors.lastname: Meador