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A Deep‐Red to Near Infrared (NIR) Fluorescent Probe Based on a Sulfur‐Modified Rhodamine Derivative with Two Spirolactone Rings

A Deep‐Red to Near Infrared (NIR) Fluorescent Probe Based on a Sulfur‐Modified Rhodamine... We report the synthesis, characterization, and photophysical and ion‐binding properties of deep‐red to near‐infrared (NIR) fluorescent rhodamine derivatives, bearing two spirolactone rings and substitution of the oxygen atoms in the xanthene ring with sulfur atoms (1‐S). The diastereoisomeric cis‐ and trans‐forms of the rhodamine derivative were separated and the cis‐form (cis‐1‐S) was structurally characterized by X‐ray crystallography. Upon treatment with Hg2+ ion, cis‐1‐S was converted into the dual spirolactone ring‐opened species, resulting in significant color change and fluorescence enhancement. Substitution of the oxygen atoms with sulfur and extended π‐conjugation across the fused six‐membered rings upon the two rings‐opening processes in the presence of Hg2+ ion led to a significant red‐shift of absorption (623 nm) and fluorescence (706 nm) peaks, compared to the ordinary rhodamine. Furthermore, the intracellular Hg2+‐sensing properties of the cis‐1‐S have been studied by confocal microscopy. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemPlusChem Wiley

A Deep‐Red to Near Infrared (NIR) Fluorescent Probe Based on a Sulfur‐Modified Rhodamine Derivative with Two Spirolactone Rings

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References (36)

Publisher
Wiley
Copyright
© 2020 Wiley‐VCH GmbH
eISSN
2192-6506
DOI
10.1002/cplu.202000384
Publisher site
See Article on Publisher Site

Abstract

We report the synthesis, characterization, and photophysical and ion‐binding properties of deep‐red to near‐infrared (NIR) fluorescent rhodamine derivatives, bearing two spirolactone rings and substitution of the oxygen atoms in the xanthene ring with sulfur atoms (1‐S). The diastereoisomeric cis‐ and trans‐forms of the rhodamine derivative were separated and the cis‐form (cis‐1‐S) was structurally characterized by X‐ray crystallography. Upon treatment with Hg2+ ion, cis‐1‐S was converted into the dual spirolactone ring‐opened species, resulting in significant color change and fluorescence enhancement. Substitution of the oxygen atoms with sulfur and extended π‐conjugation across the fused six‐membered rings upon the two rings‐opening processes in the presence of Hg2+ ion led to a significant red‐shift of absorption (623 nm) and fluorescence (706 nm) peaks, compared to the ordinary rhodamine. Furthermore, the intracellular Hg2+‐sensing properties of the cis‐1‐S have been studied by confocal microscopy.

Journal

ChemPlusChemWiley

Published: Aug 1, 2020

Keywords: ; ; ; ;

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