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875226.pdf (5.34 MB)

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2024-09-20

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cc-by (c) Betkhoshvili, Sergi, et al., 2024
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/222933

A Leap from Diradicals to Tetraradicals by Topological Control of π-Conjugation.

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Recurs relacionat

https://doi.org/10.1021/acs.joc.4c01375

Resum

In this work, we explore the series of diradical(oid)s based on 2,2′-(5,11-dihydroindolo[3,2-b]carbazole-3,9-diyl)-dimalononitrile (further referred to as PH). Hydrogen atoms in the central benzenoid (CB) ring of PH are substituted by the seriesof substituents with various lengths of π-conjugated chain and electron-donating or electron-withdrawing properties to study howthey modulate the diradical character of the parent compound. The diradical character of molecules increases up to 88−89% by twogroups doubly bonded to both sides of the CB ring of PH in para relative positions. This breaks the direct π-conjugation betweenunpaired electrons that gives rise to two radical centers and restricts the minimal polyradical identity of the compound todiradical. We show that diradicals and tetraradicals can be designed, and their polyradical character can be modulated by controlling the topology of π-conjugation as long as there is sufficient aromatic stabilization. Henceforth, the bridge between diradicals and tetraradicals is established, leading to the tetraradical(oid) molecule, which has been predicted to have narrow low-spin to high-spin energy gaps in our recent Letter.

Matèries

Compostos aromàtics, Molècules, Ressonància

Matèries (anglès)

Aromatic compounds, Molecules, Resonance

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Articles publicats en revistes (Química Inorgànica i Orgànica)
Articles publicats en revistes (Institut de Química Teòrica i Computacional (IQTCUB))

Citació

BETKHOSHVILI, Sergi, et al. A Leap from Diradicals to Tetraradicals by Topological Control of π-Conjugation. Journal of Organic Chemistry. 2024. Vol. 89, num. 14006-14020. ISSN 0022-3263. [consulted: 4 of August of 2026]. Available at: https://hdl.handle.net/2445/222933

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