Stability of the polyynic form of C18, C22, C26, and C30nanorings: a challenge tackled by range-separated double-hybrid density functionals

Brémond, Éric; Pérez-Jiménez, Ángel J.; Adamo, Carlo; Sancho-García, Juan-Carlos

doi:10.1039/d1cp04996h

Cited by 19 publications

(17 citation statements)

References 93 publications

(94 reference statements)

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“…Recently, c-CC[ n ] have gained much attention due to their promising properties. 48,93–106 Among the cyclic carbon chains, c-CC[18] has been recently synthesized. 101…”

Section: Resultsmentioning

confidence: 99%

“…The BLAs of even-numbered c-CC[ n ] have been extensively investigated in recent years. 95–97,99,100,102–106 As there are two types of bonds ( i.e. , the alternating long and short bonds) in even-numbered c-CC[ n ], the BLA of even-numbered c-CC[ n ] is defined as the difference between the average long and short bond lengths in even-numbered c-CC[ n ].…”

Section: Resultsmentioning

confidence: 99%

“…Recently, c-CC[n] have gained much attention due to their promising properties. 48,[93][94][95][96][97][98][99][100][101][102][103][104][105][106] Among the cyclic carbon chains, c-CC [18] has been recently synthesized. 101 In our previous study, only TAO-LDA, which contains no exact exchange, has been employed to study the ground-state properties of c-CC[n] (with n ¼ 10-100).…”

Section: B Cyclic Carbon Chainsmentioning

confidence: 99%

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TAO-DFT fictitious temperature made simple

Chen

Chai

2022

RSC Adv.

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“…Recently, c-CC[ n ] have gained much attention due to their promising properties. 48,93–106 Among the cyclic carbon chains, c-CC[18] has been recently synthesized. 101…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: B Cyclic Carbon Chainsmentioning

confidence: 99%

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TAO-DFT fictitious temperature made simple

Chen

Chai

2022

RSC Adv.

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“…The two isomers are predicted to have CCSs differing by less than 2% and are probably not distinguishable or separable using the ion mobility stage of the instrument. Third, conducting excited-state calculations for the cyclic clusters is challenging, and the results are of uncertain reliability, especially considering that even the ground states of neutral carbon rings are notoriously difficult to describe computationally. − …”

Section: Resultsmentioning

confidence: 99%

Disentangling Electronic Spectra of Linear and Cyclic Hydrogenated Carbon Cluster Cations, C_2n+1H⁺ (n = 3–10)

et al. 2022

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Electronic spectra are measured for protonated carbon clusters (C2n+1H+) containing between 7 and 21 carbon atoms. Linear and cyclic C2n+1H+ isomers are separated and selected using a drift tube ion mobility stage before being mass selected and introduced into a cryogenically cooled ion trap. Spectra are measured using a two-color resonance-enhanced photodissociation strategy, monitoring C2n+1 + photofragments (H atom loss channel) as a function of excitation wavelength. The linear C7H+, C9H+, C11H+, C13H+, C15H+, and C17H+ clusters, which are predicted to have polyynic structures, possess sharp 11Σ+ ← X̃1Σ+ transitions with well-resolved vibronic progressions in C–C stretch vibrational modes. The vibronic features are reproduced by spectral simulations based on vibrational frequencies and geometries calculated with time-dependent density functional theory (ωB97X-D/cc-pVDZ level). The cyclic C15H+, C17H+, C19H+, and C21H+ clusters exhibit weak, broad transitions at a shorter wavelength compared to their linear counterparts. Wavelengths for the origin transitions of both linear and cyclic isomers shift linearly with the number of constituent carbon atoms, indicating that in both cases, the clusters possess a common structural motif.

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“…In 2019, an isolated cyclo[18]carbon (C18) molecule was generated on the surface, and the polyynic structure was revealed by bond-resolved atomic force microscopy (AFM) 13,14 . Such an experimental advance further promotes the development of modern theories on the prediction of structures of cyclocarbons up to C100 [15][16][17][18][19][20][21][22][23][24] . Recently, the cyclo[16]carbon has also been synthesized and characterized on the surface, revealing its polyynic structure 25 .…”

mentioning

confidence: 94%

Aromatic annular carbon allotropes: cumulenic cyclo[10]carbon and Peierls-transition-intermediate cyclo[14]carbon

Sun

Zheng

Gao

et al. 2023

Preprint

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Cyclo[n]carbon allotropes built from sp-hybridized carbon atoms have aroused substantial interests, but until now even their structures (i.e., polyynic or cumulenic) and stabilities (i.e., cyclic or linear) are still under debate. Due to their high reactivity, it is rather difficult to synthesize in condensed phase, which hampers further real-space characterizations. Recently, isolated cyclo[18]carbon (C18) and cyclo[16]carbon (C16) molecules were generated on the surface by atom manipulation, which allowed to identify the polyynic structure of C18 and C16. More interestingly, for the smaller cyclo[n]carbon, questions arise: is it still stable in cyclic form? If so, what is the structure? Here, we successfully produce two aromatic cyclocarbons, that is, cyclo[10]carbon (C10) and cyclo[14]carbon (C14), via tip-induced dehalogenation and followed by retro-Bergman reaction of fully chlorinated naphthalene (C10Cl8) and anthracene (C14Cl10) molecules, on a bilayer NaCl/Au(111) surface at 4.7 kelvin. The cumulenic structure of C10 and Peierls-transition intermediate of C14, different from the polyynic structure of C18 and C16, are revealed by bond-resolved atomic force microscopy. Our results demonstrate a universal synthetic strategy to generate aromatic cyclo[n]carbons on the surface, opening an avenue for characterizing a series of annular carbon allotropes for the structure and stability.

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Stability of the polyynic form of C₁₈, C₂₂, C₂₆, and C₃₀nanorings: a challenge tackled by range-separated double-hybrid density functionals

Abstract: We calculate the relative energy between the cumulene and polyyne structures of a set of C4k+2 (k=4-7) rings (C18, C22, C26, and C30 prompted by the recent synthesis of the...

Cited by 19 publications

References 93 publications

TAO-DFT fictitious temperature made simple

TAO-DFT fictitious temperature made simple

Disentangling Electronic Spectra of Linear and Cyclic Hydrogenated Carbon Cluster Cations, C_2n+1H⁺ (n = 3–10)

Aromatic annular carbon allotropes: cumulenic cyclo[10]carbon and Peierls-transition-intermediate cyclo[14]carbon

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Stability of the polyynic form of C18, C22, C26, and C30nanorings: a challenge tackled by range-separated double-hybrid density functionals

Abstract: We calculate the relative energy between the cumulene and polyyne structures of a set of C4k+2 (k=4-7) rings (C18, C22, C26, and C30 prompted by the recent synthesis of the...

Cited by 19 publications

References 93 publications

TAO-DFT fictitious temperature made simple

TAO-DFT fictitious temperature made simple

Disentangling Electronic Spectra of Linear and Cyclic Hydrogenated Carbon Cluster Cations, C2n+1H+ (n = 3–10)

Aromatic annular carbon allotropes: cumulenic cyclo[10]carbon and Peierls-transition-intermediate cyclo[14]carbon

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Product

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Stability of the polyynic form of C₁₈, C₂₂, C₂₆, and C₃₀nanorings: a challenge tackled by range-separated double-hybrid density functionals

Disentangling Electronic Spectra of Linear and Cyclic Hydrogenated Carbon Cluster Cations, C_2n+1H⁺ (n = 3–10)