Reversible Photocapture of a [2]Rotaxane Harnessing a Barbiturate Template

Arnaud Tron, Peter J. Thornton, Christophe Lincheneau, Jean-pierre Desvergne, Neil Spencer, James H. R. Tucker, Nathan D. Mcclenaghan

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)


Photoirradiation of a hydrogen-bonded molecular complex comprising acyclic components, namely, a stoppered thread (1) with a central barbiturate motif and an optimized doubly anthracene-terminated acyclic Hamilton-like receptor (2b), leads to an interlocked architecture, which was isolated and fully characterized. The sole isolated interlocked photoproduct (Φ = 0.06) is a [2]rotaxane, with the dimerized anthracenes assuming a head-to-tail geometry, as evidenced by NMR spectroscopy and consistent with molecular modeling (PM6). A different behavior was observed on irradiating homologous molecular complexes 1⊂2a, 1⊂2b, and 1⊂2c, where the spacers of 2a, 2b, and 2c incorporated 3, 6, and 9 methylene units, respectively. While no evidence of interlocked structure formation was observed following irradiation of 1⊂2a, a kinetically labile rotaxane was obtained on irradiating the complex 1⊂2c, and ring slippage was revealed. A more stable [2]rotaxane was formed on irradiating 1⊂2b, whose capture is found to be fully reversible upon heating, thereby resetting the system, with some fatigue (38%) after four irradiation–thermal reversion cycles.
Original languageEnglish
Pages (from-to)988-996
JournalThe Journal of Organic Chemistry
Issue number2
Early online date5 Dec 2014
Publication statusPublished - 16 Jan 2015


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