A Kekulé Diradicaloid with a Naphthalene Spacer
The availability of a diverse array of carbenes led to the generation of a catalog of carbene based Kekulé diradicaloids, but the linker in such molecules is mostly limited to phenylene or biphenylene. Here we have prepared a closed-shell Kekulé diradicaloid (2) separated by a naphthalene moiety and stabilized by two capping 5-SIDipp [5-SIDipp = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-ylidene] from the reduction of the corresponding dication (1). The combined experimental and computational studies confirm that 2 is in a closed-shell singlet state exhibiting a singlet–triplet energy difference (ΔES–T) of 18.7 kcal/mol, which is considerably lower than Thiele’s version (29.1 kcal/mol).
Authors
- Srinu Tothadi (ORCID: https://orcid.org/0000-0001-6840-6937)
- Kumar Vanka (ORCID: https://orcid.org/0000-0001-7301-7573)
- Soumya Ranjan Dash (ORCID: https://orcid.org/0000-0001-7267-6104)
- Sakya S. Sen (ORCID: https://orcid.org/0000-0002-4955-5408)
- Gargi Kundu (ORCID: https://orcid.org/0000-0003-3029-2895)
- Debjit Pramanik (ORCID: https://orcid.org/0009-0006-7514-8335)
- Aryya Ghosh
- Ravi Kumar
Institutions
- Central Salt and Marine Chemicals Research Institute (IN)
- National Chemical Laboratory (IN)
- Ashoka University (IN)
- Institute for Analytical Instrumentation (RU)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organometallics
- Published
- 2026-03-11
- DOI
- https://doi.org/10.1021/acs.organomet.5c00508
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00