Stable π-electron systems and new aromatic structures

Reid, D. H.

doi:10.1016/0040-4020(58)80039-3

Cited by 139 publications

(109 citation statements)

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“…[17][18][19][20][21] This problem was partially overcome by the preparation of the 2,5,8-tri-(tert-butylphenalenyl) radical (2). [22] Phenalenyl 2 can not undergo s dimerization as a result of the steric hindrance provided by the tert-butyl groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Physical Properties of a Partial π‐Stacked Phenalenyl‐Based Neutral Radical Molecular Conductor

Sarkar

Itkis

Tham

et al. 2011

Chemistry A European J

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We report the synthesis, crystallization, and solid-state characterization of the 3,7-ethoxy-substituted spirobiphenalenyl-boron neutral radical 22. The radical is distinguished by its low disproportionation energy and one-dimensional structure. We show that our strategy of substitution of OEt group at the active positions of the phenalenyl units changes the crystal packing from its previously known OMe analogue and the solid-state properties are dictated by the partial π-stack structure and the oxygen atoms at the 3,7-positions and can be best rationalized in terms of the resonating valence bond model. Magnetic susceptibility measurements show that in the solid state the radical remains paramagnetic but there is significant spin-spin interaction between the molecules. Band structure calculations reflect efficient overlap between the molecules along the π stack and show evidence of interactions between the spin-bearing oxygen atoms. The room temperature electrical conductivity (σ(RT)=2.0×10(-2) S cm(-1)) of 22 is higher than that observed in previously known one-dimensional phenalenyl radicals.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Physical Properties of a Partial π‐Stacked Phenalenyl‐Based Neutral Radical Molecular Conductor

Sarkar

Itkis

Tham

et al. 2011

Chemistry A European J

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“…4 Later, Agranat proposed reactive intermediates, E and Z biphenalenylidene (E, Z 10) and dihydroperopyrene (11), for the decomposition pathway from 2 to 3 (Scheme 4). 39 However, these intermediates have not been experimentally determined because of the rapid decomposition into 3.…”

Section: Decomposition Of Phenalenyl Radicalmentioning

confidence: 99%

“…Phenalenyl radical (1) has long played an important role in organic radical chemistry because of its high stability and unique electronic structure. Compound 1 is an odd alternant hydrocarbon radical, and owing to its highly symmetric (D 3h ) structure, an unpaired electron is delocalized on six equivalent carbon atoms (1,3,4,6,7, and 9 positions: the α position), as shown in Figure 1. This spin delocalization leads to the thermodynamic stability of 1.…”

Section: Introductionmentioning

confidence: 99%

“…2 Compound 1 was rst generated by the air oxidation of phenalene 3 and later by the air oxidation of phenalenyl anion ( Figure 3). 4 In the initial studies on the phenalenyl chemistry, a major concern was the effect of resonance stabilization in 1 on its reactivity and properties. Generally, the two most important factors in the stabilization of long lived radicals are resonance stabilization and steric protection.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in the Chemistry of Phenalenyl

Uchida¹,

Kubo

2016

J. Synth. Org. Chem. Jpn.

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Phenalenyl radical is an odd alternant hydrocarbon radical with a highly symmetric (D 3h ) structure. The high stability and amphoteric redox nature of this radical have triggered studies on its chemical reactivity, physical properties, and functionalities. The main problem hindering the use of phenalenyl radicals as the molecular components of functional materials is their propensity to σ dimerization. Challenging issue will lie in understanding the self association character and also in controlling the molecular overlap motif. This article summarizes our studies on the self association behavior of phenalenyl radicals.

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“…1e5 It has attracted considerable interest since it has interesting magnetic, 6e10 optical, 8,11,12 and electronic properties. 13 The phenalenyl radical, the smallest open shell graphene, 14 was first prepared by Reid 6 and independently detected by Calvin. 15 It is a resonance-stabilised radical 16 that can be generated and observed at room temperature in solution, showing thermodynamic high stability but some kinetic instability.…”

Section: Introductionmentioning

confidence: 99%