Issue 11, 2013
From the journal:

Organic & Biomolecular Chemistry

An acid catalyzed reversible ring-opening/ring-closure reaction involving a cyano-rhodamine spirolactam†

Honglin Li,a   Hong Guan,a   Xinrui Duan,a   Jun Hu,a   Guiren Wangb  and  Qian Wang*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, USA
E-mail: wang263@mailbox.sc.edu

b Department of Mechanical Engineering and Biomedical Engineering Program, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, USA

Abstract

Cyanamide was introduced into the rhodamine spirolactam framework to produce a colorless and non-fluorescent compound RBCN. It shows a reversible ring-opening/ring-closure process in response to the solution pH, which exhibits an “ON/OFF” switching in its fluorescence. Different from other rhodamine-type dyes, the ring-open form of RBCN is stable in protic solvents under neutral, near neutral and basic conditions, showing a pink color and very strong fluorescence. We also demonstrated the potential of RBCN in live cell imaging.

Graphical abstract: An acid catalyzed reversible ring-opening/ring-closure reaction involving a cyano-rhodamine spirolactam

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Article information

DOI
https://doi.org/10.1039/C3OB27356C
Article type
Communication
Submitted
04 Dec 2012
Accepted
18 Jan 2013
First published
22 Jan 2013

Org. Biomol. Chem., 2013,11, 1805-1809

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An acid catalyzed reversible ring-opening/ring-closure reaction involving a cyano-rhodamine spirolactam

H. Li, H. Guan, X. Duan, J. Hu, G. Wang and Q. Wang, Org. Biomol. Chem., 2013, 11, 1805 DOI: 10.1039/C3OB27356C

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