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Peck EM, Collins CG, Smith BD. Thiosquaraine rotaxanes: synthesis, dynamic structure, and oxygen photosensitization. Org Lett. 2013;15(11):2762-5doi: 10.1021/ol401097f.
Peck, E. M., Collins, C. G., & Smith, B. D. (2013). Thiosquaraine rotaxanes: synthesis, dynamic structure, and oxygen photosensitization. Organic letters, 15(11), 2762-5. https://doi.org/10.1021/ol401097f
Peck, Evan M, et al. "Thiosquaraine rotaxanes: synthesis, dynamic structure, and oxygen photosensitization." Organic letters vol. 15,11 (2013): 2762-5. doi: https://doi.org/10.1021/ol401097f
Peck EM, Collins CG, Smith BD. Thiosquaraine rotaxanes: synthesis, dynamic structure, and oxygen photosensitization. Org Lett. 2013 Jun 07;15(11):2762-5. doi: 10.1021/ol401097f. Epub 2013 May 17. PMID: 23682842.
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Org Lett. 2013 Jun 07;15(11):2762-5. doi: 10.1021/ol401097f. Epub 2013 May 17.

Thiosquaraine rotaxanes: synthesis, dynamic structure, and oxygen photosensitization.

Organic letters

Evan M Peck, Carleton G Collins, Bradley D Smith

Affiliations

  1. Department of Chemistry and Biochemistry, 236 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA.

PMID: 23682842 DOI: 10.1021/ol401097f

Abstract

Thiosquaraine dyes have sulfur atoms instead of oxygens on the central squaraine core, and they are powerful singlet oxygen photosensitizers. Stability studies show that they are susceptible to attack by nucleophiles. This problem was circumvented by preparing a mechanically interlocked thiosquaraine rotaxane. NMR studies of the rotaxane indicate an unusual dynamic molecular structure due to a nonsymmetrical coconformation. Upon irradiation with red light, the thiosquaraine rotaxane generates the same amount of singlet oxygen as the known photosensitizer methylene blue.

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