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Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes
Abstract
A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N'-Dicyclohexyl-1,7-dibromoperylene bisimide 1,7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure 1,7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a-c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo-7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield.
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Yan, C., Barlow, S., Wang, Z., Yan, H., Jen, A. K.-Y., Marder, S. R., & Zhan, X. (2018) · Nature Reviews Materials · doi:10.1038/natrevmats.2018.3 · Cited by 2,710
Schmidt, R., Oh, J. H., Sun, Y.-S., Deppisch, M., Krause, A.-M., Radacki, K., Braunschweig, H., Könemann, M., Erk, P., Bao, Z., et al. (2009) · Journal of the American Chemical Society · doi:10.1021/ja901077a · Cited by 666
Self-citationLiang, Y., Pan, Y., Chen, L., Li, P., Xu, M., Zhou, H., Lu, X., Hu, W., Yin, C., & Fan, Q. (2024) · Angewandte Chemie International Edition · doi:10.1002/anie.202408861 · Cited by 22
Metadata
- Authors
- Würthner, F., Stepanenko, V., Chen, Z., Saha-Möller, C. R., Kocher, N., & Stalke, D.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-10-19
- Volume
- 69
- Issue
- 23
- Pages
- 7933-7939
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2019751164
- Cited by
- 345
- References
- 0
- FWCI
- 6.99
- Type
- journal article
- Language
- en
- Open access
- closed
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- Würthner, F., Stepanenko, V., Chen, Z., Saha-Möller, C. R., Kocher, N., & Stalke, D. (2004). Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes. The Journal of Organic Chemistry. https://doi.org/10.1021/jo048880d
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