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

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.
AuthorsEvan M Peck, Carleton G Collins, Bradley D Smith
JournalOrganic letters (Org Lett) Vol. 15 Issue 11 Pg. 2762-5 (Jun 07 2013) ISSN: 1523-7052 [Electronic] United States
PMID23682842 (Publication Type: Journal Article)

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