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Synthesis and Properties of Benzo‐Fused Indeno[2,1‐ c ]fluorenes
Author(s) -
JousselinOba Tanguy,
Deal Parker E.,
Fix Aaron G.,
Frederickson Conerd K.,
Vonnegut Chris L.,
Yassar Abderrahim,
Zakharov Lev N.,
Frigoli Michel,
Haley Michael M.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801684
Subject(s) - antiaromaticity , chemistry , molecule , conjugated system , cyclic voltammetry , annulation , affinities , aromaticity , core (optical fiber) , stereochemistry , photochemistry , crystallography , materials science , organic chemistry , electrochemistry , catalysis , electrode , polymer , composite material
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.