Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls

Syguła, Andrzej; Rabideau, Peter W.

doi:10.1002/3527607994.ch12

Cited by 51 publications

(16 citation statements)

References 39 publications

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“…Bond length, bond angle, and torsion angle among carbon atoms are nearly constant on the basis of their hybrid orbitals. On the other hand, unusual geometrical parameters have been reported for highly strained molecules, such as sterically congested and/or curved polycyclic aromatic hydrocarbons [1][2][3][4][5][6][7][8] as well as cyclic p-conjugated molecules, including cycloparaphenylenes, [9][10][11][12][13][14][15][16][17] which are endowed with special properties that the ordinary hydrocarbons do not have. In these novel aromatic compounds, the pyramidalization of C sp 2 carbons and the bond and torsion angles that deviate from the standard values are responsible for the formation of distorted structures.…”

Section: Introductionmentioning

confidence: 99%

Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å

Ishigaki

Shimajiri

Takeda

et al. 2018

Chem

114

109

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Compounds with an ultralong CC single bond have been successfully constructed in three steps from commercially available dihalo aromatics. The intramolecular ''core-shell strategy'' is a key tactic for stabilizing compounds with an ultralong CC bond. Using this concept could lead to an even longer CC bond (''hyper covalent bonds'' with a bond length of 1.8-2.0 Å) because the covalently bonded state and non-bonded state are seamlessly connected in terms of the interatomic distance.

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Section: Introductionmentioning

confidence: 99%

Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å

Ishigaki

Shimajiri

Takeda

et al. 2018

Chem

114

109

View full text Add to dashboard Cite

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“…π –Conjugated systems have attracted much attention due to the facile modification of their properties by unique molecular design, as shown in several reports on sterically-congested and/or curved polycyclic aromatic hydrocarbons (PAHs) [ 1 , 2 , 3 , 4 ]. Some of them have been shown to have unusual geometric features, such as extremely twisted aromatic rings [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ] or an extraordinarily long C–C bond [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ], which result in intriguing physical properties.…”

Section: Introductionmentioning

confidence: 99%

9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior

et al. 2017

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The title dispiro hydrocarbon 1 was designed as a new electrochromic material. This multiply clamped hexaphenylethane-type electron donor was prepared from 2,2′-diiodobiphenyl via biphenyl-2,2′-diylbis(dibenzotropylium) 22+ salt. X-ray analysis of 1 revealed a highly strained structure as reflected by an elongated “ethane” bond [bond length: 1.6665(17) Å] and nearly eclipsed conformation. The weakened bond was cleaved upon two-electron oxidation to regenerate the deeply colored dication 22+. The reversible interconversion between 1 and 22+ is accompanied not only by a drastic color change but also by C–C bond formation/cleavage. Thus, the voltammogram showed a pair of well-separated redox waves, which is characteristic of “dynamic redox (dyrex)” behavior. The tetrahydro derivative of 1 with two units of spiro(dibenzocycloheptadiene), which suffers from more severe steric congestion, was also prepared. The crystallographically determined bond length for the central C–C bond [1.705(4) Å] is greatest among the values reported for 9,9,10,10-tetraaryl-9,10-dihydrophenanthrene derivatives.

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“…Extended -conjugated molecules have been widely investigated for their unique physical properties that can be modified by proper molecular design. In particular, much attention has been focused on sterically congested and/or curved polycyclic aromatic hydrocarbons (PAHs) [1][2][3][4][5][6][7][8][9][10][11][12][13][14] as well as cyclic -conjugated molecules like cycloparaphenylenes [15][16][17][18][19][20][21] and carbon nanobelts. [22][23][24] These highly strained molecules are potential candidates with special characteristic features that are not found in normal compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

Photo- and Thermal Interconversion of Multiconfigurational Strained Hydrocarbons Exhibiting Completely Switchable Oxidation to Stable Dicationic Dyes

2019

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Highly strained hydrocarbons with two di-/tri-benzocycloheptatriene units were designed as electrochromic overcrowded ethylenes that undergo reversible interconversion with stable dicationic dyes. Due to severe steric repulsion, two configurational isomers (anti,anti-folded and syn,anti-folded forms) were isolated as stable entities. Photo-and thermal interconversion of these isomers proceeded cleanly: one-way photoisomerization occurred from anti,anti-to syn,anti-form and one-way thermal isomerization was observed from syn,anti-to anti,anti-form. Even though both isomers undergo twoelectron oxidation into the same twisted dications, quite different oxidation potentials enable completely selective oxidation of syn,anti-isomers. Thus, the present multi-configurational strained hydrocarbons are capable of switching of activation/deactivation of their electrochromic properties by light/heat.

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Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls

Cited by 51 publications

References 39 publications

Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å

Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å

9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior

Photo- and Thermal Interconversion of Multiconfigurational Strained Hydrocarbons Exhibiting Completely Switchable Oxidation to Stable Dicationic Dyes

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