Face-to-face fixed ferrocenes. Synthesis and properties of 2,10-diferrocenyl- and 2,5,7,10-tetraferrocenyl-1,6-methano[10]annulenes

Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene

“…Iyoda et al prepared several ferrocenyl-substituted annulenes through Negishi-type couplings with the hopes of constructing ferromagnetic materials on account of the cofacial interactions and electronic communication present among the organometallic fragments. [67] Starting synthetically from a cycloheptatriene, recent work by Kajioka et al prepared hole-transporting triarylamines whose amorphous solidstate properties made them suitable electroluminescent OLED materials. [68] To the best of our knowledge, there are no reports describing the incorporation of the methano [10]annulenes into the backbones of semiconducting organic polymers.…”

Non-Traditional Aromatic Topologies and Biomimetic Assembly Motifs as Components of Functional Pi-Conjugated Oligomers

“…We initiated our explorations with the methano[10]annulene ring system, a remarkable hydrocarbon whose synthesis was developed by Professor Emanuel Vogel in the mid-1960s [ 7 ]. Although a variety of more complex electronic molecules have been built from this annulene core over the intervening decades [ 8 , 9 , 10 ], we were not aware of any studies to incorporate this 10 pi-electron aromatic molecule into conjugated polymers, either for solution or thin-film solid-state measurements. Larger aromatics such as the 14 pi-electron dihydrodimethylpyrene have been included into conjugated polymers but have not been compared in a side-by-side sense to more classical benzenoid aromatics [ 11 , 12 ].…”

Synthesis, Structure, and Properties of Aromatic Ring-Layered Polymers Containing Ferrocene as a Terminal Unit

“…(Scheme 1 and Table I) Two related model compounds 7 and 8 were prepared according to the reactions shown in Two cyclopentadienyl rings were arranged in a face-to-face manner [42][43][44][45][46][47][48][49]. The molecular structure of 8 possessing the [2.2]paracyclophane unit between two ferrocenes is depicted in Figure 2.…”