A Kekulé Diradicaloid with a Naphthalene Spacer

Organometallics 2026

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Authors: Gargi Kundu, Debjit Pramanik, Soumya Ranjan Dash, Ravi Kumar, Srinu Tothadi, Aryya Ghosh, Kumar Vanka, Sakya S. Sen
DOI: 10.1021/acs.organomet.5c00508
Cited by: 0
References: 30

Abstract

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 (ΔE S–T ) of 18.7 kcal/mol, which is considerably lower than Thiele’s version (29.1 kcal/mol).

Fields of Study & Subjects

Synthesis and Properties of Aromatic Compounds Synthesis and characterization of novel inorganic/organometallic compounds Photolysis and Reactive Intermediates

Publication details

Journal / source
Organometallics
Volume
45
Issue
6
Pages
624–627
Publication date
11 March 2026
Language
EN