Synthesis and Properties of Benzo‐Fused Indenofluorenes

A set of fully‐conjugated indenofluorenes has been synthesized and confirmed by solid‐state structure analysis. The indeno[2,1‐c]fluorenes and their benzo‐fused analogues all contain the antiaromatic as‐indacene core. The molecules possess high electron affinities and show a broad absorption that re...

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Published in:Chemistry, an Asian journal an Asian journal, 2019-05, Vol.14 (10), p.1737-1744
Main Authors: Tanguy Jousselin‐Oba, Deal, Parker E, Fix, Aaron G, Frederickson, Conerd K, Vonnegut, Chris L, Yassar, Abderrahim, Zakharov, Lev N, Frigoli, Michel, Haley, Michael M
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Language:English
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Aromatic compounds
Chemical reactions
Chemistry
Organic chemistry
Structural analysis
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container_end_page 1744
container_issue 10
container_start_page 1737
container_title Chemistry, an Asian journal
container_volume 14
creator Tanguy Jousselin‐Oba
Deal, Parker E
Fix, Aaron G
Frederickson, Conerd K
Vonnegut, Chris L
Yassar, Abderrahim
Zakharov, Lev N
Frigoli, Michel
Haley, Michael M
description A set of fully‐conjugated indenofluorenes has been synthesized and confirmed by solid‐state structure analysis. The indeno[2,1‐c]fluorenes and their benzo‐fused analogues all contain the antiaromatic as‐indacene core. The molecules possess high electron affinities and show a broad absorption that reaches into the near‐IR region of the electromagnetic spectrum. All of the featured compounds reversibly accept up to two electrons as revealed by cyclic voltammetry. Analysis of molecule tropicity using NICS‐XY scan calculations shows that, while the as‐indacene core is less paratropic than s‐indacene, benz[a]‐annulation further reduces the antiaromaticity of the core. Antiaromatic strength of the as‐indacene core can also be tuned by the position of fusion of additional arenes on the outer rings.
doi_str_mv 10.1002/asia.201801684
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subjects Aromatic compounds
Chemical reactions
Chemistry
Organic chemistry
Structural analysis
title Synthesis and Properties of Benzo‐Fused Indenofluorenes
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