Cycloalkyl-aminomethylrhodamines: pH dependent photophysical properties tuned by cycloalkane ring size.

A series of fluorescent pH probes based on the spiro-cyclic rhodamine core, aminomethylrhodamines (AMR), was synthesized and the effect of cycloalkane ring size on the acid/base properties of the AMR system was explored. The study involved a series of rhodamine 6G (cAMR6G) and rhodamine B (cAMR) pH probes with cycloalkane ring sizes from C-3 to C-6 on the spiro-cyclic amino group. It is known that the pKa value of cycloalkylamines can be tuned by different ring sizes in accordance with the Baeyer ring strain theory.