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Anilinomethylrhodamines: pH sensitive probes with tunable photophysical properties by substituent effect.


ABSTRACT: A series of pH dependent rhodamine analogues possessing an anilino-methyl moiety was developed and shown to exhibit a unique photophysical response to pH. These anilinomethylrhodamines (AnMR) maintain a colorless, nonfluorescent spirocyclic structure at high pH. The spirocyclic structures open in mildly acidic conditions and are weakly fluorescent; however, at very low pH, the fluorescence is greatly enhanced. The equilibrium constants of these processes show a linear response to substituent effects, which was demonstrated by the Hammett equation.

SUBMITTER: Best QA 

PROVIDER: S-EPMC3992268 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Anilinomethylrhodamines: pH sensitive probes with tunable photophysical properties by substituent effect.

Best Quinn A QA   Liu Chuangjun C   van Hoveln Paul D PD   McCarroll Matthew E ME   Scott Colleen N CN  

The Journal of organic chemistry 20131009 20


A series of pH dependent rhodamine analogues possessing an anilino-methyl moiety was developed and shown to exhibit a unique photophysical response to pH. These anilinomethylrhodamines (AnMR) maintain a colorless, nonfluorescent spirocyclic structure at high pH. The spirocyclic structures open in mildly acidic conditions and are weakly fluorescent; however, at very low pH, the fluorescence is greatly enhanced. The equilibrium constants of these processes show a linear response to substituent eff  ...[more]

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