Chemical Oxidation Induced Aromaticity Switching of <i>E</i>-Ethylene Bridged [38] Octaphyrin (1.2.1.0.1.2.1.0) with NIR Absorption
We report the syntheses, spectroscopic analyses, and solid-state structural evidence of a quasi-planar aromatic [38] <i>E</i>-ethylene bridged octaphyrin (1.2.1.0.1.2.1.0) exhibiting NIR absorption. The chemical oxidation using an appropriate oxidant led to unique π reconstruction via amine-imine conversion and/or C-oxygenation of the inverted thiophene rings resulting in weakly antiaromatic or nonaromatic [36] octaphyrins with preserved <i>E</i>-conformation of the ethylene moieties. The aromatic nature of the studied octaphyrins is supported by GIMIC calculations of the magnetically induced ring current density.
Authors
- Dage Sundholm (ORCID: https://orcid.org/0000-0002-2367-9277)
- P.K. Chatterjee
- Harapriya Rath (ORCID: https://orcid.org/0000-0002-5507-5275)
- Daniel Blasco (ORCID: https://orcid.org/0000-0001-9291-6187)
- Sumit Sahoo (ORCID: https://orcid.org/0000-0002-5807-7153)
Institutions
- University of Helsinki (FI)
- Indian Association for the Cultivation of Science (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-06
- DOI
- https://doi.org/10.1021/acs.orglett.4c04203
- Citations
- 3
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.35
Funders
- University Grants Commission
- Academy of Finland
- Science and Engineering Research Board