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Synthesis and assembly of self-complementary calix[4]arenes.
Open accessAbstract
A calix[4]arene was designed to reversibly dimerize and form an egg-shaped enclosure. Adhesive interactions in the assembly were provided by four self-associating ureas, which form a cyclic array containing 16 hydrogen bonds. The synthesis was completed in four steps from the previously described O,O',O",O"'-tetrabenzylcalix[4]arene. Evidence for dimerization of the calixarene tetraurea was provided by H NMR, mass spectrometry, and the observation of encapsulated molecules. The resulting cavity was of sufficient size to capture guests such as ethyl benzene and p-xylene.
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Citations
Cited by
Self‐Assembly in Natural and Unnatural Systems
Philp, D., & Stoddart, J. F. (1996) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199611541 · Cited by 2,115
A chiral spherical molecular assembly held together by 60 hydrogen bonds
MacGillivray, L. R., & Atwood, J. L. (1997) · Nature · doi:10.1038/38985 · Cited by 1,198
Cohen, Y., Avram, L., & Frish, L. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200300637 · Cited by 1,122
Conn, M. M., & Rebek, J. (1997) · Chemical Reviews · doi:10.1021/cr9603800 · Cited by 1,075
Self-citationElectrolyte transport in the mammalian colon: mechanisms and implications for disease
Kunzelmann, K., & Mall, M. (2002) · Physiological Reviews · doi:10.1152/physrev.00026.2001 · Cited by 655
Metadata
- Authors
- Shimizu, K. D., & Rebek, J.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 1995-12-19
- Volume
- 92
- Issue
- 26
- Pages
- 12403-12407
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2087113524
- Cited by
- 278
- References
- 0
- FWCI
- 8.16
- Type
- journal article
- Language
- en
- Open access
- green
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- Shimizu, K. D., & Rebek, J. (1995). Synthesis and assembly of self-complementary calix[4]arenes. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.92.26.12403
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