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Synthesis of BN-Fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation
Abstract
A tandem intramolecular electrophilic arene borylation reaction has been developed for the synthesis of BN-fused polycyclic aromatic compounds such as 4b-aza-12b-boradibenzo[g,p]chrysene (A) and 8b,11b-diaza-19b,22b-diborahexabenzo[a,c,fg,j,l,op]tetracene. These compounds adopt a twisted conformation, which results in a tight and offset face-to-face stacking array in the solid state. Time-resolved microwave conductivity measurements prove that the intrinsic hole mobility of A is comparable to that of rubrene, one of the most commonly used organic semiconductors, indicating that BN-substituted PAHs are potential candidates for organic electronic materials.
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te Velde, G., Bickelhaupt, F. M., Baerends, E. J., Fonseca Guerra, C., van Gisbergen, S. J. A., Snijders, J. G., & Ziegler, T. (2001) · Journal of Computational Chemistry · doi:10.1002/jcc.1056 · Cited by 10,152
Cited by
Hatakeyama, T., Shiren, K., Nakajima, K., Nomura, S., Nakatsuka, S., Kinoshita, K., Ni, J., Ono, Y., & Ikuta, T. (2016) · Advanced Materials · doi:10.1002/adma.201505491 · Cited by 2,379
Self-citationNarrowband deep-blue organic light-emitting diode featuring an organoboron-based emitter
Kondo, Y., Yoshiura, K., Kitera, S., Nishi, H., Oda, S., Gotoh, H., Sasada, Y., Yanai, M., & Hatakeyama, T. (2019) · Nature Photonics · doi:10.1038/s41566-019-0476-5 · Cited by 1,545
Self-citationMamada, M., Hayakawa, M., Ochi, J., & Hatakeyama, T. (2024) · Chemical Society Reviews · doi:10.1039/d3cs00837a · Cited by 482
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Baranac‐Stojanović, M. (2014) · Chemistry – A European Journal · doi:10.1002/chem.201402851 · Cited by 90
Metadata
- Authors
- Hatakeyama, T., Hashimoto, S., Seki, S., & Nakamura, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-10-31
- Volume
- 133
- Issue
- 46
- Pages
- 18614-18617
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2015904059
- Cited by
- 335
- References
- 1
- FWCI
- 7.63
- Type
- journal article
- Language
- en
- Open access
- closed
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- Hatakeyama, T., Hashimoto, S., Seki, S., & Nakamura, M. (2011). Synthesis of BN-Fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation. Journal of the American Chemical Society. https://doi.org/10.1021/ja208950c
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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