Issue 57, 2024

Cyano disubstituted tetrabenzoindeno[2,1-a]fluorene: open-shell or closed-shell?

Abstract

Organic diradicaloids have lately emerged as potential spintronic materials. We report the unprecedented synthesis of a near-IR absorbing indeno[2,1-a]fluorene derivative that displays remarkably low LUMO (−4.15 eV) and a small HOMO–LUMO gap (0.85 eV). NMR/EPR studies indicated its open-shell diradical property, which was supported by DFT calculations while suggesting a 30% diradical character and a small singlet (S)–triplet (T) gap (−2.52 kcal mol−1). A large bond length alternation of the as-indacene core for its single-crystals indicated a quinoidal contribution with greater antiaromaticity, which is in line with the small diradical character despite showing a small S–T gap.

Graphical abstract: Cyano disubstituted tetrabenzoindeno[2,1-a]fluorene: open-shell or closed-shell?

Supplementary files

Article information

Article type
Communication
Submitted
09 Yan 2024
Accepted
07 Mud 2024
First published
07 Mud 2024

Chem. Commun., 2024,60, 7319-7322

Cyano disubstituted tetrabenzoindeno[2,1-a]fluorene: open-shell or closed-shell?

P. K. Sharma, P. Jana, S. Bandyopadhyay and S. Das, Chem. Commun., 2024, 60, 7319 DOI: 10.1039/D4CC00683F

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