jo0c01387_si_004.cif (763.42 kB)
Late-Stage Modification of Electronic Properties of Antiaromatic and Diradicaloid Indeno[1,2‑b]fluorene Analogues via Sulfur Oxidation
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posted on 2020-08-06, 22:00 authored by Justin J. Dressler, Joshua E. Barker, Lucas J. Karas, Hannah E. Hashimoto, Ryohei Kishi, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gomez-Garcia, Masayoshi Nakano, Judy I. Wu, Michael M. HaleyThe
ability to alter optoelectronic and magnetic properties of
molecules at a late stage in their preparation is in general a nontrivial
feat. Here, we report the late-stage oxidation of benzothiophene-fused
indacenes and dicyclopentanaphthalenes to their corresponding sulfone
derivatives. We find that while such modifications increase the highest
occupied molecular orbital (HOMO)–lowest unoccupied molecular
orbital (LUMO) energy gap to a small degree, other properties such
as HOMO and LUMO energy levels, molecule paratropicity, and singlet-triplet
energy gaps are influenced to a greater degree. The most surprising
finding is a change of the bond alternation pattern within the s-indacene core of the sulfones. Computations corroborate
the experimental findings and offer plausible explanations for these
changes in molecular properties.
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nontrivial featHOMOindacene coreLUMO energy levelssulfone derivativesfluorene AnaloguesSulfur Oxidationmolecule paratropicitymodifications increaseLate-Stage Modificationenergy gaplate-stage oxidationbenzothiophene-fused indacenesElectronic Propertiesbond alternation patternsinglet-triplet energy gaps
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