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Synthesis of Bispyrenyl Sugar-Aza-Crown Ethers as New Fluorescent Molecular Sensors for Cu(II)
Abstract
Two N-pyrenylacetamide-substituted sugar-aza-crown ethers have been synthesized as new fluorescent chemosensors. The designed ligands 1 and 2 exhibit fluorescence characteristics of a pyrene monomer and a dynamic excimer emission when compared to N-pyrenylacetamide as a model compound. Both ligands displayed a Cu2+-sensitive fluorescence quenching with a 1:1 stoichiometry and high stability constants (log K = 6.7 for 1 and 7.8 for 2). The quenching effect was rationalized on the basis of photoinduced electron transfer from the excited pyrene to the complexed Cu2+ cation, while the changes in excimer-to-monomer ratio were explained by a conformational analysis through DFT calculations. The predicted structure suggests that the Cu2+ cation is coordinated with the two carbonyl groups and the sugar-aza-crown ethers which rigidified the complex structure and placed the two pyrene moieties far apart.
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Barnham, K. J., Masters, C. L., & Bush, A. I. (2004) · Nature Reviews Drug Discovery · doi:10.1038/nrd1330 · Cited by 3,683
Cited by
Zhao, Y., Zhang, X.-B., Han, Z.-X., Qiao, L., Li, C.-Y., Jian, L.-X., Shen, G.-L., & Yu, R.-Q. (2009) · Analytical Chemistry · doi:10.1021/ac901127n · Cited by 455
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Metadata
- Authors
- Xie, J., Ménand, M., Maisonneuve, S., & Métivier, R.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-07-12
- Volume
- 72
- Issue
- 16
- Pages
- 5980-5985
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1999657001
- Cited by
- 171
- References
- 1
- FWCI
- 6.83
- Type
- journal article
- Language
- en
- Open access
- closed
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- Xie, J., Ménand, M., Maisonneuve, S., & Métivier, R. (2007). Synthesis of Bispyrenyl Sugar-Aza-Crown Ethers as New Fluorescent Molecular Sensors for Cu(II). The Journal of Organic Chemistry. https://doi.org/10.1021/jo070315y
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