GSH　is　one　of　the　most　important　reducing　agents　in　biological　systems.　The　depletion　of　GSH　in　the　human　body　is　linked　to　many　diseases.　Therefore,　it　is　necessary　to　develop　suitable　and　efficient　probes　for　detecting　GSH　concentrations　in　real　samples.　In　this　work,　we　designed　and　synthesized　two　near-infrared　emitting　iridium(iii)　complex　probes　containing　a　novel　ligand　functionalized　with　an　α,β-unsaturated　ketone　for　the　rapid　and　sensitive　detection　of　GSH.　The　molecular　structure　of　Ir2　was　determined　by　X-ray　crystallography.　Due　to　their　large　Stokes　shift,　long　luminescence　lifetime　and　NIR　emission,　these　probes　were　successfully　applied　in　the　imaging　of　GSH　in　living　cells.　In　addition,　two　iridium(iii)　complexes　have　strong　singlet　oxygen　generation　ability　which　can　be　used　for　photodynamic　therapy　(PDT)　upon　visible　light　irradiation.　On　the　basis　of　these　findings,　our　iridium(iii)　complexes　may　serve　as　GSH　probes　for　HeLa　cell　imaging　and　as　photosensitizers　for　PDT.　©　2023　The　Royal　Society　of　Chemistry.