Chemistry Reference
In-Depth Information
Indenofluorenes and Derivatives: Syntheses
and Emerging Materials Applications
Aaron G. Fix, Daniel T. Chase, and Michael M. Haley
Abstract The growing demand for flexible electronic devices and hydrogen
storage materials has spurred a resurgence of interest in polyaryl hydrocarbons
including graphene, acenes, fullerenes, polythiophenes, etc. Indenofluorenes are
another polyaryl molecular scaffold that has shown utility in the organic and hybrid
materials arena, with polymers incorporating the indeno[1,2-
b
]fluorene moiety
being common in organic light emitting diodes. This review examines the syntheses
and properties of the five distinct indenofluorene regioisomers, with a focus on
small molecule applications in organic electronics of this intriguing and somewhat
underexplored family of polyaryl hydrocarbons.
Keywords Acene
Indenofluorene
Organic electronics
Polyarene
Polycyclic
aromatic hydrocarbon
Terphenyl
Contents
1
Introduction .................................................................................. 160
1.1 Background ............................................................................ 160
1.2 Early Research . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 162
2
Indeno[1,2-
a
]fluorenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 165
2.1 Indeno[1,2-
a
]fluorene-7,12-diones ................................................... 165
2.2 Other Indeno[1,2-
a
]fluorenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166
3
Indeno[1,2-
b
]fluorenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 167
3.1 Indeno[1,2-
b
]fluorene-6,12-diones ................................................... 167
3.2 Indeno[1,2-
b
]fluorene-6,12-olefins . . . ................................................ 172
3.3 Fully-Conjugated Indeno[1,2-
b
]fluorene . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 174
3.4 Other Indeno[1,2-
b
]fluorenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 179
