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PreprintCC BY-NC-NDChemRxiv

Globally Aromatic 10-Boratetraoxacorroles: Boron-Doped Macrocyclic Chromophores with Intense Red-to-Near-Infrared Emission

  • Jonas Fehler1,2,3
  • Lukas Swoboda1,2,3
  • Alexandra Friedrich1,2,3
  • Vivien Schütz1,2,3
  • Holger Helten1,2,3
  1. 1Institute of Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg, Germany, 97074
  2. 2Institute for Sustainable Chemistry & Catalysis with Boron (ICB)
  3. 3Julius-Maximilians-Universität Würzburg
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Abstract

Neutral, globally aromatic boron-containing macrocycles are exceptionally rare, with the 10-bora-21,22,23,24-tetraoxacorroles reported herein representing only the second class of such compounds known to date, following the 5-bora-21,22-dioxaporphyrin we recently described, and are also the first neutral, globally aromatic boracorroles. Here, we present a furan-based 10-bora-21,22,23,24-tetraoxacorrole and an oxadiborepin-fused derivative thereof. The global aromaticity of both macrocyclic boranes in the neutral state is supported by experimental data and NICS and ACID cal­culations. They exhibit intense absorption spanning the ultraviolet to near-infrared (NIR) regions of the electromagnetic spectrum. Notably, the novel boracorroles display bright red and red-to-NIR fluorescence, achiev­ing quantum yields more than twice (Φ fl = 35–46%) that of conventional triphenylcorrole (Φ fl = 19%). DFT analysis reveals that the frontier orbital en­ergies are strongly modulated by the meso- B atom, generating a large HOMO to HOMO−1 energy gap and, consequently, mark­edly enhanced Q-band extinction coefficients arising from the predominantly single-configurational character of the S 0 →S 1 transition (HOMO to LUMO). Incorporation of the BOB bridge in the oxadiborepin-fused derivative significantly stabilizes the LUMO, giving rise to red-shifted absorption and emission alongside distinct electrochemical behavior. In addition, the BOB unit further amplifies the global aromaticity of the boracorrole, underscoring efficient π-conjugation across this heteroatomic bridge.

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Cite

BibTeXRIS
BibTeX
@misc{fehler2026globally,
  title = {{Globally Aromatic 10-Boratetraoxacorroles: Boron-Doped Macrocyclic Chromophores with Intense Red-to-Near-Infrared Emission}},
  author = {Jonas Fehler and Lukas Swoboda and Alexandra Friedrich and Vivien Schütz and Holger Helten},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15004419/v2},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15004419/v2},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Globally Aromatic 10-Boratetraoxacorroles: Boron-Doped Macrocyclic Chromophores with Intense Red-to-Near-Infrared Emission
AU  - Jonas Fehler
AU  - Lukas Swoboda
AU  - Alexandra Friedrich
AU  - Vivien Schütz
AU  - Holger Helten
PY  - 2026
DA  - 2026/09/17
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15004419/v2
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15004419/v2
AB  - Neutral, globally aromatic boron-containing macrocycles are exceptionally rare, with the 10-bora-21,22,23,24-tetraoxacorroles reported herein representing only the second class of such compounds known to date, following the 5-bora-21,22-dioxaporphyrin we recently described, and are also the first neutral, globally aromatic boracorroles. Here, we present a furan-based 10-bora-21,22,23,24-tetraoxacorrole and an oxadiborepin-fused derivative thereof. The global aromaticity of both macrocyclic boranes in the neutral state is supported by experimental data and NICS and ACID cal­culations. They exhibit intense absorption spanning the ultraviolet to near-infrared (NIR) regions of the electromagnetic spectrum. Notably, the novel boracorroles display bright red and red-to-NIR fluorescence, achiev­ing quantum yields more than twice (Φ fl = 35–46%) that of conventional triphenylcorrole (Φ fl = 19%). DFT analysis reveals that the frontier orbital en­ergies are strongly modulated by the meso- B atom, generating a large HOMO to HOMO−1 energy gap and, consequently, mark­edly enhanced Q-band extinction coefficients arising from the predominantly single-configurational character of the S 0 →S 1 transition (HOMO to LUMO). Incorporation of the BOB bridge in the oxadiborepin-fused derivative significantly stabilizes the LUMO, giving rise to red-shifted absorption and emission alongside distinct electrochemical behavior. In addition, the BOB unit further amplifies the global aromaticity of the boracorrole, underscoring efficient π-conjugation across this heteroatomic bridge.
ER  -