Aromaticity and Antiaromaticity in the Excited States of Porphyrin Nanorings
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Abstract
Aromaticity can be a useful concept for predicting the behavior of excited states. Here we show that π-conjugated porphyrin nanorings exhibit size-dependent excited-state global aromaticity and antiaromaticity for rings containing up to eight porphyrin subunits, although they have no significant global aromaticity in their neutral singlet ground states. Applying Baird’s rule, even rings ([4n] π-electrons) are aromatic in their lowest excited states, whereas the lowest excited states of odd rings ([4n + 2] π-electrons) are antiaromatic. These predictions are borne out by density functional theory (DFT) studies of the nucleus-independent chemical shift (NICS) in the T1 triplet state of each ring, which reveal the critical importance of the triplet delocalization to the emergence of excited-state aromaticity. The singlet excited states (S1) are explored by measurements of the radiative rate and fluorescence peak wavelength, revealing a subtle odd–even alternation as a function of ring size, consistent with symmetry breaking in antiaromatic excited states.
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LC-ωhPBE (ω = 0.1) generally gives NICS values that are consistent with experimental NMR shifts.
“We found that LC-ωhPBE (ω = 0.1) generally gives NICS values that are consistent with experimental NMR shifts. 2,4,36”
From From Macrocycles to Quantum Rings: Does Aromaticity Have a Size Limit? (2021) · cites this paper as [36]
In the section labeled Abstract (page unavailable), the paper says it calculated NICS values using LC-ωHPBE with ω = 0.1 among other functionals. It does not report that this functional’s NICS values generally agree with experimental NMR shifts; it instead emphasizes that NICS values are sensitive to the chosen functional. (LLM, conf=0.83)
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Behmagham, F., Arshadi, S., Ghnim, Z. S., Rajiv, A., Adhab, A. H., Shankhyan, A., Mahdi, M. S., Mansoor, A. S., Radi, U. K., & Abd, N. S. (2025) · Computational and Theoretical Chemistry · doi:10.1016/j.comptc.2025.115230 · Cited by 3 · see citing works
NICS—nucleus-independent chemical shift
Gershoni‐Poranne, R., & Stanger, A. (2021) · Dialnet (Universidad de la Rioja) · Cited by 3 · see citing works
MacLeod‐Carey, D., & Muñoz‐Castro, A. (2023) · Physical Chemistry Chemical Physics · doi:10.1039/d2cp05326h · Cited by 3 · see citing works
Insight into magnetically induced ring currents and photophysics of six-porphyrin nanorings
Valiulina, L. I., Cherepanov, V. N., & Khoroshkin, K. (2024) · Physical Chemistry Chemical Physics · doi:10.1039/d4cp02547d · Cited by 3 · see citing works
Moallem, A., Arshadi, S., Emami, M. R. S., Khaghani, A., Salary, M., & Marvi, O. (2025) · Journal of Molecular Graphics and Modelling · doi:10.1016/j.jmgm.2025.109198 · Cited by 2 · see citing works
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Tetrahedral Al20O30 Cage: A Superchalcogen Atom
Sun, Z., Shi, L., & Cheng, L. (2025) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.4c06789
Synthesis and Properties of Unusually Stable Antiaromatic Porphyrinoids
Tripathi, N., & Ravikanth, M. (2026) · European Journal of Organic Chemistry · doi:10.1002/ejoc.70590
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- Authors
- Peeks, M. D., Gong, J. Q., McLoughlin, K., Kobatake, T., Haver, R., Herz, L. M., & Anderson, H. L.
- Affiliations
- University of Oxford (GB)
- University of Oxford , , ,
- Corresponding author
- Peeks, Martin D.
- Anderson, Harry L.
- Venue
- The Journal of Physical Chemistry Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-04-05
- Volume
- 10
- Issue
- 8
- Pages
- 2017-2022
- ISSN
- 1948-7185 (ISSN-L)
- PMC
- PMC6488184
- OpenAlex
- W2932253631
- Cited by
- 49
- References
- 57
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 4 · 2023: 6 · 2022: 9 · 2021: 17 · 2020: 5 · 2019: 3
- FWCI
- 3.07
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Locations
- The Journal of Physical Chemistry Letters (publishedVersion, cc-by)
- ChemRxiv (acceptedVersion, cc-by-nc-nd)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- UNSWorks (University of New South Wales, Sydney, Australia) (submittedVersion, cc-by-nc-nd)
- Royal College of Surgeons in Ireland (submittedVersion, cc-by-nc-nd)
- Funders
- H2020 European Research Council (320969)
- Engineering and Physical Sciences Research Council (EP/J007161/1, EP/M016110/1)
- Exeter College, University of Oxford (NA)
- Nippon Shokubai Ltd. (NA)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- porphyrin nanorings, excited-state aromaticity, antiaromaticity, Baird's rule, nucleus-independent chemical shift, triplet state, singlet excited state, π-conjugated macrocycles, odd-even effect, symmetry breaking, fluorescence
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