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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]

PMID: 24050117

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