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pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic
Xiangkun Si1, Wanyi Yu1, Naikun Song2
1The Key Laboratory of Biomedical Information Engineering of Ministry of Education, School of Life Science and Technology, Xi'an Jiaotong University, No. 28 West Xianning Road, Xi'an, 710049, People's Republic of China.
Abstract:
We report new photoluminescent switching systems achieved through pH-induced intramolecular oxa-Michael conjugate addition reactions. Ratiometric absorbance and fluorescence emission were observed across conjugate acceptors triggered by pH, resulting in specific pseudo pKa values. The effect of substituents on the pseudo pKa's was investigated, showing increased values from electron-withdrawing to electron-donating groups. Inspired by the physiologically related pKa, a fluorescent probe was designed, successfully distinguishing cancer cells from normal cells through live cellular imaging.
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