The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Efficient Templated Synthesis of Donor−Acceptor Rotaxanes Using Click Chemistry
Abstract
The mild reaction conditions, remarkable functional group compatibility, and complete regioselectivity of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition ("click chemistry") between organic azides and terminal alkynes have led to a threading-followed-by-stoppering approach to the synthesis of donor-acceptor rotaxanes incorporating cyclobis(paraquat-p-phenylene) (CBPQT4+) as the pi-accepting ring component. Rotaxane formation is initiated by reacting azide-functionalized pseudorotaxanes containing pi-donating 1,5-dioxynaphthalene (DNP) recognition units with appropriate alkyne-functionalized stoppers. The high yields obtained in this efficient, kinetically controlled post-assembly covalent modification, as well as the excellent convergence of the synthetic protocol, are demonstrated by the preparation of [2]-, [3]-, and [4]rotaxanes containing multiple DNP/CBPQT4+ donor-acceptor recognition motifs.
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Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
The convergence of synthetic organic and polymer chemistries
Hawker, C. J., & Wooley, K. L. (2005) · Science · doi:10.1126/science.1109778 · Cited by 1,298
Riva, R., Schmeits, S., Stoffelbach, F., Jérôme, C., Jérôme, R., & Lecomte, P. (2005) · Chemical Communications · doi:10.1039/b510282k · Cited by 208
Metadata
- Authors
- Dichtel, W. R., Miljanić, O. Š., Spruell, J. M., Heath, J. R., & Stoddart, J. F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-07-25
- Volume
- 128
- Issue
- 32
- Pages
- 10388-10390
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2037021610
- Cited by
- 184
- References
- 3
- FWCI
- 16.35
- Type
- journal article
- Language
- en
- Open access
- closed
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