Two thiazole-fused fluoran-based fluorescent probes for selective and sensitive sensing copper ions and cell imaging application

Abstract

In this work, two thiazole-fused fluoran-based fluorescent probes 8′-(diethylamino)-2-((2-hydroxyethyl) amino)spiro[isoindoline-1,11′-xantheno[2, 1-d]thiazol]-3-one (TFH) and (8′-(diethylamino)-2-((2-hydroxyethyl)amino)-3′-methyl-3-oxospiro[isoindoline-1,11′-xantheno[2,1-d]thiazol]-3′-ium).BF4 (MTFH) have been prepared for copper ions. It should be noted that MTFH achieves red emission (632 nm) compared with TFH in the presence of copper ion, which mainly can be attributed to the methylation of molecule MTFH that induced more stronger ICT effect. The two probes show selective fluorescence off-on signal changes towards copper ions with detection limits of 8.8 and 60.8 nM. Copper ion detection can be conducted in a wide pH range including the physiological pH environment. Both TFH and MTFH exhibit suitable cytotoxicity and have been used for copper ion tracing in living cells. However, no other significant improvements of MTFH in sensing performance can be observed when compared with TFH.