# Graphyne

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Allotrope of carbon

Not to be confused with [Graphene](/source/Graphene), [Grapheme](/source/Grapheme), or [Graphane](/source/Graphane).

Graphyne Chemical structure of graphyne-1 Identifiers CAS Number 1300713-38-5 CompTox Dashboard (EPA) DTXSID201336806 Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Graphyne-*n* varieties, where *n* indicates the number of carbon–carbon triple bonds in a link between two adjacent hexagons. Graphyne is graphyne-1; graphdiyne is graphyne-2.

**Graphyne** is an [allotrope](/source/Allotrope) of [carbon](/source/Carbon). Although it has been studied in theoretical models, it is very difficult to synthesize and only small amounts of uncertain purity have been created. Its structure is one-atom-thick [planar](/source/Planar_crystallographic_group) sheets of sp and [sp2-bonded](/source/Sp2_bond) carbon atoms arranged in crystal lattice. It can be seen as a lattice of [benzene](/source/Benzene) rings connected by [acetylene](/source/Acetylene) bonds. The material is called graphyne-*n* when benzene rings are connected by *n* sequential acetylene molecules, and **graphdiyne** for a particular case of *n* = 2 ([diacetylene](/source/Diacetylene) links).

Depending on the content of acetylene groups, graphyne can be considered a mixed hybridization, sp*k*, where k can be 1 or 2,[1][2] and thus differs from the hybridization of [graphene](/source/Graphene) (considered pure sp2) and [diamond](/source/Diamond) (pure sp3).

First-principles calculations showed that periodic graphyne structures and their [boron nitride](/source/Boron_nitride) analogues are stable. The calculations used [phonon dispersion curves](/source/Phonon_scattering) and [ab-initio](/source/Ab_initio) finite temperature, quantum mechanical [molecular dynamics](/source/Molecular_dynamics) simulations.[3]

## History

Graphyne was first theoretically proposed by Baughman et al. in 1987.[4] In 2010, Li et al. developed the first successful methodology for creating graphdiyne films using the Glaser–Hay [cross-coupling reaction](/source/Cross-coupling_reaction) with hexaethynylbenzene.[5] The proposed approach makes it possible to synthesize nanometer-scale graphdiyne and graphtetrayne, which lack long-range order. In 2019, Cui and co-workers reported on a mechanochemical technique for obtaining graphyne using benzene and [calcium carbide](/source/Calcium_carbide).[6] Although a gram-scale graphyne can be obtained using this approach, graphynes with long-range crystallinity over a large area remain elusive.

In 2022, synthesis of multi-layered γ‑graphyne was successfully performed through the polymerization of 1,3,5-tribromo-2,4,6-triethynylbenzene under [Sonogashira coupling](/source/Sonogashira_coupling) conditions. [Near-infrared spectroscopy](/source/Near-infrared_spectroscopy) and [cyclic voltammetry](/source/Cyclic_voltammetry) of the material determined the [bandgap](/source/Bandgap) as 0.48 ± 0.05 eV, which agrees with the theoretical prediction for graphyne-based materials.[7]: 4[8]

## Synthesis

Despite numerous efforts by different approaches, no synthesis method has been discovered to create quality graphyne. The small impure amounts created to date do not allow characterization sufficient to verify theoretical properties.[7]: 12

## Structure

Through the use of computer models scientists have predicted several properties of the substance on assumed geometries of the lattice. Its proposed structures are derived from inserting acetylene bonds in place of [carbon-carbon single bonds](/source/Carbon-carbon_bond) in a graphene lattice.[9] Graphyne is theorized to exist in multiple geometries. This variety is due to the multiple arrangements of sp and sp2 hybridized carbon. The proposed geometries include a [hexagonal lattice structure](/source/Hexagonal_crystal_system) and a [rectangular lattice structure](/source/Cubic_crystal_system).[10] Out of the theorized structures the rectangular lattice of 6,6,12-graphyne may hold the most potential for future applications.

## Properties

Models predict that graphyne has the potential for [Dirac cones](/source/Dirac_cone) on its double and triple bonded carbon atoms.[*[citation needed](https://en.wikipedia.org/wiki/Wikipedia:Citation_needed)*] Due to the Dirac cones, the [conduction](/source/Conduction_band) and [valence bands](/source/Valence_band) meet in a linear fashion at a single point in the [Fermi level](/source/Fermi_level). The advantage of this scheme is that electrons behave as if they have no mass, resulting in energies that are proportional to the momentum of the electrons. Like in graphene, hexagonal graphyne has electric properties that are direction independent. However, due to the symmetry of the proposed rectangular 6,6,12-graphyne the electric properties would change along different directions in the plane of the material.[10] This unique feature of its symmetry allows graphyne to [self-dope](/source/Doping_(semiconductor)) meaning that it has two different Dirac cones lying slightly above and below the Fermi level.[10] The self-doping effect of 6,6,12-graphyne can be effectively tuned by applying in-plane external strain.[11] Graphyne samples synthesized to date have shown a melting point of 250-300 °C, low reactivity in decomposition reactions with oxygen, heat and light.[9]

## Potential applications

It has been hypothesized that graphyne is preferable to graphene for specific applications owing to its particular energy structure, namely direction-dependent Dirac cones.[12][13] The directional dependency of 6,6,12-graphyne could allow for electrical [grating](/source/Diffraction_grating) on the nanoscale.[14] This could lead to the development of faster transistors and nanoscale electronic devices.[10][15][16] Recently it was demonstrated that [photoinduced electron transfer](/source/Photoinduced_electron_transfer) from electron-donating partners to γ-graphyne is favorable and occurs on nano to sub-picosecond time scale.[17]

## References

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1. **[^](#cite_ref-3)** Özçelik, V. Ongun; Ciraci, S. (January 10, 2013). "Size Dependence in the Stabilities and Electronic Properties of α-Graphyne and Its Boron Nitride Analogue". *The Journal of Physical Chemistry C*. **117** (5): 2175–2182. [arXiv](/source/ArXiv_(identifier)):[1301.2593](https://arxiv.org/abs/1301.2593). [doi](/source/Doi_(identifier)):[10.1021/jp3111869](https://doi.org/10.1021%2Fjp3111869). [S2CID](/source/S2CID_(identifier)) [44136901](https://api.semanticscholar.org/CorpusID:44136901).

1. **[^](#cite_ref-4)** Baughman, R. H.; Eckhardt, H.; Kertesz, M. (1987). "Structure-property predictions for new planar forms of carbon: Layered phases containing sp2 and sp atoms". *The Journal of Chemical Physics*. **87** (11): 6687–6699. [Bibcode](/source/Bibcode_(identifier)):[1987JChPh..87.6687B](https://ui.adsabs.harvard.edu/abs/1987JChPh..87.6687B). [doi](/source/Doi_(identifier)):[10.1063/1.453405](https://doi.org/10.1063%2F1.453405).

1. **[^](#cite_ref-5)** Li, G.; Li, Y.; Lui, H.; Guo, Y.; Li, Y.; Zhu, D. (2010). "Architecture of graphdiyne nanoscale films". *Chemical Communications*. **46** (19): 3256–3258. [doi](/source/Doi_(identifier)):[10.1039/B922733D](https://doi.org/10.1039%2FB922733D). [PMID](/source/PMID_(identifier)) [20442882](https://pubmed.ncbi.nlm.nih.gov/20442882).

1. **[^](#cite_ref-6)** Li, Q.; Yang, C.; Wu, L.; Wang, H.; Cui, X. (2019). "Converting benzene into γ-graphyne and its enhanced electrochemical oxygen evolution performance". *Journal of Materials Chemistry A*. **7** (11): 5981–5990. [doi](/source/Doi_(identifier)):[10.1039/C8TA10317H](https://doi.org/10.1039%2FC8TA10317H). [S2CID](/source/S2CID_(identifier)) [104431102](https://api.semanticscholar.org/CorpusID:104431102).

1. ^ [***a***](#cite_ref-LiHan2023Review_7-0) [***b***](#cite_ref-LiHan2023Review_7-1) Li, Jiaqiang; Han, Yu (2023-03-01). ["Artificial carbon allotrope γ-graphyne: Synthesis, properties, and applications"](https://doi.org/10.1016%2Fj.giant.2023.100140). *Giant*. **13** 100140. [doi](/source/Doi_(identifier)):[10.1016/j.giant.2023.100140](https://doi.org/10.1016%2Fj.giant.2023.100140). [hdl](/source/Hdl_(identifier)):[10754/687549](https://hdl.handle.net/10754%2F687549). [ISSN](/source/ISSN_(identifier)) [2666-5425](https://search.worldcat.org/issn/2666-5425).

1. **[^](#cite_ref-8)** Desyatkin, V. G.; Martin, W. B.; Aliev, A. E.; Chapman, N. E.; Fonseca, A. F.; Galvão, D. S.; Miller, E. R.; Stone, K. H.; Wang, Z.; Zakhidov, D.; Limpoco, F. T.; Almahdali, S. R.; Parker, S. M.; Baughman, R. H.; Rodionov, V. O. (2022). "Scalable Synthesis and Characterization of Multilayer γ‑Graphyne, New Carbon Crystals with a Small Direct Band Gap". *Journal of the American Chemical Society*. **144** (39): 17999–18008. [arXiv](/source/ArXiv_(identifier)):[2301.05291](https://arxiv.org/abs/2301.05291). [Bibcode](/source/Bibcode_(identifier)):[2022JAChS.14417999D](https://ui.adsabs.harvard.edu/abs/2022JAChS.14417999D). [doi](/source/Doi_(identifier)):[10.1021/jacs.2c06583](https://doi.org/10.1021%2Fjacs.2c06583). [PMID](/source/PMID_(identifier)) [36130080](https://pubmed.ncbi.nlm.nih.gov/36130080). [S2CID](/source/S2CID_(identifier)) [252438218](https://api.semanticscholar.org/CorpusID:252438218).

1. ^ [***a***](#cite_ref-arxiv_9-0) [***b***](#cite_ref-arxiv_9-1) Kim, Bog G.; Choi, Hyoung Joon (2012). "Graphyne: Hexagonal network of carbon with versatile Dirac cones". *[Physical Review B](/source/Physical_Review_B)*. **86** (11) 115435. [arXiv](/source/ArXiv_(identifier)):[1112.2932](https://arxiv.org/abs/1112.2932). [Bibcode](/source/Bibcode_(identifier)):[2012PhRvB..86k5435K](https://ui.adsabs.harvard.edu/abs/2012PhRvB..86k5435K). [doi](/source/Doi_(identifier)):[10.1103/PhysRevB.86.115435](https://doi.org/10.1103%2FPhysRevB.86.115435). [S2CID](/source/S2CID_(identifier)) [119288235](https://api.semanticscholar.org/CorpusID:119288235).

1. ^ [***a***](#cite_ref-physicsworld_10-0) [***b***](#cite_ref-physicsworld_10-1) [***c***](#cite_ref-physicsworld_10-2) [***d***](#cite_ref-physicsworld_10-3) Dumé, Belle (1 March 2012). ["Could graphynes be better than graphene?"](http://physicsworld.com/cws/article/news/2012/mar/01/could-graphynes-be-better-than-graphene). *[Physics World](/source/Physics_World)*. [Institute of Physics](/source/Institute_of_Physics).

1. **[^](#cite_ref-11)** Wang, Gaoxue; Si, Mingsu; Kumar, Ashok; Pandey, Ravindra (May 26, 2014). "Strain engineering of Dirac cones in graphyne". *Applied Physics Letters*. **104** (21): 213107. [Bibcode](/source/Bibcode_(identifier)):[2014ApPhL.104u3107W](https://ui.adsabs.harvard.edu/abs/2014ApPhL.104u3107W). [doi](/source/Doi_(identifier)):[10.1063/1.4880635](https://doi.org/10.1063%2F1.4880635).

1. **[^](#cite_ref-12)** Malko, Daniel; Neiss, Christian; Viñes, Francesc; Görling, Andreas (24 February 2012). ["Competition for Graphene: Graphynes with Direction-Dependent Dirac Cones"](http://diposit.ub.edu/dspace/bitstream/2445/65316/1/619276.pdf) (PDF). *[Phys. Rev. Lett.](/source/Phys._Rev._Lett.)* **108** (8) 086804. [Bibcode](/source/Bibcode_(identifier)):[2012PhRvL.108h6804M](https://ui.adsabs.harvard.edu/abs/2012PhRvL.108h6804M). [doi](/source/Doi_(identifier)):[10.1103/PhysRevLett.108.086804](https://doi.org/10.1103%2FPhysRevLett.108.086804). [hdl](/source/Hdl_(identifier)):[2445/65316](https://hdl.handle.net/2445%2F65316). [PMID](/source/PMID_(identifier)) [22463556](https://pubmed.ncbi.nlm.nih.gov/22463556).

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## External links

Wikimedia Commons has media related to [Graphyne](https://commons.wikimedia.org/wiki/Category:Graphyne).

- Rawat, Sachin (2022-08-05). ["Graphene is a Nobel Prize-winning "wonder material." Graphyne might replace it"](https://bigthink.com/the-future/graphyne/). *Big Think*. Retrieved 2022-08-07.

- Wang, Xiluan; Shi, Gaoquan (2015). "An introduction to the chemistry of graphene". *Physical Chemistry Chemical Physics*. **17** (43). Royal Society of Chemistry (RSC): 28484–28504. [Bibcode](/source/Bibcode_(identifier)):[2015PCCP...1728484W](https://ui.adsabs.harvard.edu/abs/2015PCCP...1728484W). [doi](/source/Doi_(identifier)):[10.1039/c5cp05212b](https://doi.org/10.1039%2Fc5cp05212b). [PMID](/source/PMID_(identifier)) [26465215](https://pubmed.ncbi.nlm.nih.gov/26465215).

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