A reverse donor-acceptor bistable [2]catenane

Ali Coskun, Sourav Saha, Ivan Aprahamian, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

48 Scopus citations


(Figure Presented) A [2]catenane, composed of a π-electron-rich bis-1,5-dioxynaphthalene[38]crown10 (BDNP38C10) ring, mechanically interlocked with a large macrocycle containing two disubstituted tetraarylmethane "speed bumps" and two different π-electron-deficient units - namely, naphthalene dimide (NpI) and bipyridinium (BIPY2+) units - has been synthesized from a [2]rotaxane, containing the former recognition unit, after performing two sequential Cu(I)-catalyzed azide-alkyne cycloadditions with a linker containing the latter recognition unit. The product, which exists as a single co-conformer, wherein the BDNP38C10 ring encircles the NpI unit, undergoes equilibration to give approximately equal amounts of the other co-conformer in which the BDNP38C10 ring encircles the BIPY2+ unit.

Original languageEnglish (US)
Pages (from-to)3187-3190
Number of pages4
JournalOrganic Letters
Issue number15
StatePublished - 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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