Renaissance of Annulene Chemistry

Spitler, Eric L.; Johnson, and Charles A.; Haley, Michael M.

doi:10.1021/cr050541c

Cited by 352 publications

(213 citation statements)

References 327 publications

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“…Whereas a large variety of aryl-and heteroaryl-fused dehydro [12]and [18] annulenes have been described (see above), [39,[71][72][73][74][75] only a limited number of such chromophores, not annellated to aromatic rings, were reported in recent years. [76] Most of them were prepared as potential precursors to cyclo[n]carbons, such as cyclo-C 18 , which, however, remain elusive as bulk materials.…”

Section: Perethynylated Dehydroannulenesmentioning

confidence: 99%

“…1), and the physical, in particular the optoelectronic properties of the parent and peripherally functionalized compounds have been investigated; [45][46][47] this work has been the subject of several recent reviews. [30,31,39,48] Appropriate peripheral decoration also enhances the self-assembly properties [33,34,49] of such shape-persistent macrocycles. [50][51][52] Continuing interest exists in probing the aromaticity [53] and antiaromaticity of these dehydroannulenes and other macrocyclic p-systems both experimentally and by advanced theoretical calculations.…”

Section: Introductionmentioning

confidence: 99%

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All‐Carbon Scaffolds by Rational Design

2010

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The search for new molecular and regular polymeric allotropes of carbon has greatly stimulated the preparation and investigation of pi-conjugated acetylenic macrocycles, which often represent substructures of proposed 2D carbon networks. Perethynylated dehydroannulenes, expanded radialenes, and radiaannulenes with large, multi-nanometer-sized all-carbon cores are potent electron acceptors, and their optoelectronic as well as stability and solubility properties are greatly enhanced by peripheral donor substitution. Acetylenic scaffolding into three dimensions has generated an expanded cubane with a C(56) core, the first representative of a new class of "platonic" objects. Exceptional chiroptical properties displayed by enantiomerically pure alleno-acetylenic, shape-persistent macrocycles promise fascinating perspectives for the development of molecular and supramolecular chiroptical materials.

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Section: Perethynylated Dehydroannulenesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

All‐Carbon Scaffolds by Rational Design

2010

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“…1). Indeed, assembled subunits of several graphyne structures [26][27][28] and another similar graphene allotrope including triple-bonded carbon linkages, so-called graphdiyne films and nanoribbons have already been synthesized. 29,30 Theoretical calculations have shown that these lowdimensional structures have unique mechanical, 24,[31][32][33] thermal, 34,35 optical, 36 and particularly electrical [37][38][39][40][41][42] properties as peculiar as those of graphene.…”

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confidence: 99%

Electronic, phononic, and thermoelectric properties of graphyne sheets

Sevinçli

Sevik

2014

Appl. Phys. Lett.

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Electron, phonon, and thermoelectric transport properties of a-, b-, c-, and 6,6,12-graphyne sheets are compared and contrasted with those of graphene. a-, b-, and 6,6,12-graphynes, with direction dependent Dirac dispersions, have higher electronic transmittance than graphene. c-graphyne also attains better electrical conduction than graphene except at its band gap. Vibrationally, graphene conducts heat much more efficiently than graphynes, a behavior beyond an atomic density differences explanation. Seebeck coefficients of the considered Dirac materials are similar but thermoelectric power factors decrease with increasing effective speeds of light. c-graphyne yields the highest thermoelectric efficiency with a thermoelectric figure of merit as high as ZT ¼ 0.45, almost an order of magnitude higher than that of graphene. V C 2014 AIP Publishing LLC.[http://dx.doi.org/10.1063/1.4902920] Graphene and its functionalized forms have many extraordinary physical properties, such as robustness, stability, flexibility, very high thermal, and electrical conductivities, 1-8 which inspired numerous studies exploring the possibilities for adapting them for technological applications in the fields of not only electronics, photonics, and optoelectronics, 9-11 but also thermoelectrics and thermal management of nano-devices. 8,[12][13][14][15][16][17][18] Recently, it was shown that other two-dimensional materials can also be stable and that they widen the potential of two-dimensional materials for applications. [19][20][21][22] Of particular importance are graphene-like carbon allotropes, called graphyne structures composed of one-atom-thick sheets of carbon atoms but containing sp carbon bonds in addition to sp 2 hybridized bonds 23-25 (see Fig. 1). Indeed, assembled subunits of several graphyne structures 26-28 and another similar graphene allotrope including triple-bonded carbon linkages, so-called graphdiyne films and nanoribbons have already been synthesized. 29,30 Theoretical calculations have shown that these lowdimensional structures have unique mechanical, 24,31-33 thermal, 34,35 optical, 36 and particularly electrical [37][38][39][40][41][42] properties as peculiar as those of graphene. For instance, 6,6,12-graphyne, exhibit direction-dependent conductivity due to its electronic structure possessing two self-doped nonequivalent distorted Dirac cones. 38 On the other hand, c-graphyne has a direct energy band gap, 43,44 which is appealing for electronic applications. 45 Considering that one of the most important concerns about graphene is the difficulty to manipulate its electronic conduction due to absence of a band gap, c-graphyne was argued to be more suitable for electronics. 46 More recently, thermoelectric properties of graphynes were reported to have interesting features. 35,47,48 Yet, the potential of graphynes for applications require further investigations.In this work, electronic, phononic, and thermoelectric transport properties of four types of graphyne structures, namely, a-, b-, c-, and 6,6,12-graphynes,...

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“…[1][2][3][4] Our initial targets were the triangular-shaped [18]DBAs, e.g., 1. 5,6 In general, the assembly of these compounds (Scheme 1) involved triynes such as 2 prepared from triazene intermediates like 3, which in turn started from commercially available or easily synthesized aniline derivatives.…”

Section: Surprising Outcomesmentioning

confidence: 99%

Coarctate cyclization reactions: a primer

2012

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The cleavage of five-membered heterocycles possessing an exocyclic carbene or nitrene to form conjugated ene-ene-yne systems has been documented for over 40 years; however, the reverse reaction, using a conjugated ''ene-ene-yne'' precursor to form a heterocycle is a relatively new approach. Over the past decade, the Haley and Herges groups have studied computationally and experimentally the cyclization of the ''hetero-ene-ene-yne'' motif via an unusual class of concerted reactions known as coarctate reactions. This feature article details our synthetic and mechanistic work involving triazene-arene-alkynes and structurally-related systems to generate heterocycles using coarctate chemistry.

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Renaissance of Annulene Chemistry

Cited by 352 publications

References 327 publications

All‐Carbon Scaffolds by Rational Design

All‐Carbon Scaffolds by Rational Design

Electronic, phononic, and thermoelectric properties of graphyne sheets

Coarctate cyclization reactions: a primer

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