ArticleNature communications2025
A fully conjugated meso-boron-substituted porphyrinoid combining Lewis acidity with redox-switchable aromaticity.
Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Triply N-Confused Hexaphyrins(1.1.1.1.1.0) Synthesized From N-Confused Hexaphyrin(2.1.1.1.1.1): Aromaticity Modulation, Metal Coordination, and Photothermal Conversion.Angewandte Chemie (International ed. in English) · 2026Article
- Limitations of MRSF-TDDFT for Applications in Photochemistry.The journal of physical chemistry letters · 2026Article
- All-solid passive organic optical limiter via coordination-bond anchoring strategy.Nature communications · 2026Article
- Merging Pyrrole with Boron into Versatile Di(2-pyrryl)borane Building Blocks: π-Extension, Polymerization, and Coordination.Angewandte Chemie (International ed. in English) · 2026Article
- Encapsulation of an Electron in a Diborencine Macrocycle: Synthesis, Structure, and Reactivity.Journal of the American Chemical Society · 2025Article
- A fully conjugated meso-boron-substituted porphyrinoid combining Lewis acidity with redox-switchable aromaticity.Nature communications · 2025Article
- Concealed antiaromaticity.Open research Europe · 2025Article
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Authors and funding
9 authors.
Funding
Abstract
The structural motif of porphyrin is relevant for many essential biological processes and has emerged as a versatile component of functional materials. Here, we introduce a thiophene-based porphyrinogen having electron-deficient boron atoms in all four meso-positions. Its fully π-conjugated backbone exhibits effectively concealed antiaromaticity, with locally confined aromaticity to the thiophene units. The macrocycle readily binds fluoride ions, signaled by changes in its photophysical characteristics. Global aromaticity is switched on via facile consecutive (electro)chemical one-electron reductions to give the radical anion and the dianion, the potassium salts both of which were isolated and characterized by single-crystal X-ray diffraction. The bowl-shaped dianion constitutes a tetrathiophene-based porphyrinoid with a metal cation in its coordination sphere. This 18-π-electron macrocycle shows absorption features typical of porphyrins, while its low-energy Q bands are unusually intense in relation to the Soret bands. In addition, it displays fluorescence emission in the near-infrared (NIR) spectral region.
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Registered trials
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