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Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
Open accessAbstract
Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (>1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of π-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants.
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Ren, A., Zhang, Y., Bian, Y., Liu, Y.-J., Zhang, Y.-X., Ren, C.-J., Zhou, Y., Zhang, T., & Feng, X.-S. (2024) · Food Chemistry · doi:10.1016/j.foodchem.2023.137086 · Cited by 98
Self-citationHall-Roberts, H., Agarwal, D., Obst, J., Smith, T. B., Monzón-Sandoval, J., Di Daniel, E., Webber, C., James, W. S., Mead, E., Davis, J. B., et al. (2020) · Alzheimer's Research & Therapy · doi:10.1186/s13195-020-00709-z · Cited by 62
Jeong, S., Mai, H. D., Nguyen, T. K., Youn, J.-S., Nam, K.-H., Park, C.-M., & Jeon, K.-J. (2021) · Applied Catalysis B: Environmental · doi:10.1016/j.apcatb.2021.120227 · Cited by 44
Metadata
- Authors
- Wang, X.-Y., Richter, M., He, Y., Björk, J., Riss, A., Rajesh, R., Garnica, M., Hennersdorf, F., Weigand, J. J., Narita, A., Berger, R., Feng, X., Auwärter, W., Barth, J. V., Palma, C.-A., & Müllen, K.
- Venue
- Nature Communications
- Published
- 2017-12-05
- Volume
- 8
- Issue
- 1
- Pages
- 1948-1948
- ISSN
- 2041-1723 (ISSN-L)
- OpenAlex
- W2769730089
- Cited by
- 883
- References
- 4
- FWCI
- 43.78
- Type
- journal article
- Language
- en
- Open access
- gold
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- Wang, X.-Y., Richter, M., He, Y., Björk, J., Riss, A., Rajesh, R., Garnica, M., Hennersdorf, F., Weigand, J. J., Narita, A., Berger, R., Feng, X., Auwärter, W., Barth, J. V., Palma, C.-A., & Müllen, K. (2017). Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling. Nature Communications. https://doi.org/10.1038/s41467-017-01934-1
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
