Synthesis and characterization of fluorinated derivatives of cresolsulfonphthalein

Alexander V Kachur; Diana Sardelis; Catherine Bentzley; Anatoliy V Popov; E James Delikatny; Joel Karp

doi:10.1016/j.jfluchem.2012.10.011

Synthesis and characterization of fluorinated derivatives of cresolsulfonphthalein

J Fluor Chem. 2013 Jan 1:145:112-117. doi: 10.1016/j.jfluchem.2012.10.011.

Authors

Alexander V Kachur¹, Diana Sardelis², Catherine Bentzley², Anatoliy V Popov³, E James Delikatny³, Joel Karp³

Affiliations

¹ Department of Radiology, School of Medicine University of Pennsylvania, Philadelphia., PA 19104 ; Department of Chemistry and Biochemistry, Misher College of Arts and Sciences, University of the Sciences, Philadelphia, PA 19104.
² Department of Chemistry and Biochemistry, Misher College of Arts and Sciences, University of the Sciences, Philadelphia, PA 19104.
³ Department of Radiology, School of Medicine University of Pennsylvania, Philadelphia., PA 19104.

Abstract

The reaction between dilute fluorine gas and cresolsufonphthalein in acetic acid was investigated. The mono-, di-, and trifluorinated cresolsufonphthalein derivatives were isolated and characterized. These compounds possessed the properties of pH indicators with biologically relevant pK_a values (6.4-7.5) and the absorption maxima of the basic forms at 582-592 nm. This method can be used for synthesis of positron-emitting ¹⁸F-labeled pH indicators with potential application for non-invasive in vivo pH measurement in biological objects.

Keywords: Cresol Purple; Fluorine; electrophilic fluorination; pH measurement.

Grants and funding

UL1 RR024134/RR/NCRR NIH HHS/United States