Abstract

Recently, long-lived, organic radical species have attracted much attention from chemists and material scientists because of their unique electronic properties derived from their magnetic spin and singly occupied molecular orbitals. Most stable and persistent organic radicals are heteroatom-centered radicals, whereas carbon-centered radicals are generally very reactive and therefore have had limited applications. Because the physical properties of carbon-centered radicals depend predominantly on the topology of the π-electron array, the development of new carbon-centered radicals is key to new basic molecular skeletons that promise novel and diverse applications of spin materials. This account summarizes our recent studies on the development of novel carbon-centered radicals, including phenalenyl, fluorenyl, and triarylmethyl radicals.

Highlights

  • Organic radical species are generally recognized as highly reactive, intermediate species

  • The π-conjugated radical high stability were found to be On ablethe to show various association modesspecies due towith steric andthermodynamic electronic effects of substituent groups

  • Other hand, it association was found that the due anthryl groupand used for kinetic stabilization has notgroups

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Summary

Introduction

Organic radical species are generally recognized as highly reactive, intermediate species. Galvinoxyl, and DPPH are well known as stable, organic, radical species, which are commercially available chemicals. These stable radical species are “heteroatom-centered radicals”, in which unpaired electrons are mainly distributed on heteroatoms. The thermodynamic stability of radical species can be evaluated by the indices such as bond dissociation energy (BDE) and radical stabilization energy (RSE) [8]. Either BDEs or RSEs may be used for evaluating the thermodynamic stability of radical species. The larger the delocalization of unpaired electrons, the more thermodynamically stabilized the radical species, and the RSE shows a larger negative value. 1 is in equilibrium with a dimer and dissociates mostly into a monomeric radical in dilute solution (about 10− 5 M), indicating high thermodynamic stability of 1.

Phenalenyl Radical
Electronic Structure of Phenalenyl Radical
Dimerizaion of Phenalenyl
3.25 Å tert-butyl groups at
H NMR spectrum of the pale yellow yellow in crystals
The enthalpy and entropy
H NMR spectrum of recorded in degassed
One-Dimensional Stack of Phenalenyl Radicals
Fof interplanar between the C6 Fthe
Fluorenyl
10. Manner
Ring Expansion of Fluorenyl Radical
12. Anthryl-substituted
Conclusions
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