Issue 6, 2013

Squaraine rotaxane shuttle as a ratiometric deep-red optical chloride sensor

Abstract

A new squaraine rotaxane molecular shuttle exhibits high chemical stability and acts as a deep-red, fluorescent and colorimetric sensor for Cl anion with reversible, ratiometric response. The molecular design encapsulates a dihydroxyl substituted squaraine dye inside an anthracene-containing tetralactam macrocycle and a “clicked capping” reaction was used to convert an appropriate pseudorotaxane precursor into a permanently interlocked rotaxane in high yield. Reversible binding of Cl to the rotaxane in solution, or on the surface of prototype dipsticks, causes lateral displacement of the surrounding macrocycle away from the central squaraine station and a substantial 30–40 nm shift in the squaraine absorption/fluorescence maxima that can be easily detected by the naked eye. The collective attributes of intense absorption/emission and ratiometric response at deep-red wavelengths is a significant advance in optical Cl sensor performance by an organic molecule.

Graphical abstract: Squaraine rotaxane shuttle as a ratiometric deep-red optical chloride sensor

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Feb 2013
Accepted
09 Apr 2013
First published
09 Apr 2013

Chem. Sci., 2013,4, 2557-2563

Squaraine rotaxane shuttle as a ratiometric deep-red optical chloride sensor

C. G. Collins, E. M. Peck, P. J. Kramer and B. D. Smith, Chem. Sci., 2013, 4, 2557 DOI: 10.1039/C3SC50535A

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