A novel ‘‘donor-π-acceptor’’ type fluorescence probe for sensing pH: mechanism and application in vivo

A novel pH fluorescent probe 1-(pyren-1-yl)-3-(6-methoxypridin-3-yl)-acrylketone, (PMPA), which had a pyrene structure attached to methoxypyridine, was synthesized for monitoring extremely acidic and alkaline pH. The pH titrations indicated that PMPA displayed a remarkable emission enhancement with a pKa of 2.70 and responded linearly to minor pH fluctuations within the extremely acidic range of 1.26–3.97. Interestingly, PMPA also exhibited strong pH-dependent characteristics with pKa 9.32 and linear response to extreme-alkalinity range of 8.54–10.36. In addition, PMPA displayed a good selectivity, excellent photostability and large Stokes shift (167nm). Furthermore, the probe PMPA had excellent cell membrane permeability and was applied successfully to rapidly detect pH in living cells. pH value in these organs was closely related to many diseases, so these findings suggested that the probe had potential application in pH detecting for disease diagnosis. [Display omitted] •A novel ‘‘donor-π-acceptor’’ type fluorescence probe (PMPA) for sensing pH was facilely synthesized.•PMPA showed high response speed, selectivity and sensitivity towards pH.•PMPA had been applied successfully to imaging in vivo.