Delivering neurochemicals serves as an important technique in the study of neurobiology and clinical applications. Among various delivery techniques, molecules capable of releasing neurochemicals upon photoirradiation is beneficial with respect to selectivity and spatiotemporal resolution. Several photodonors have been devised so far, but most of them were based on coordination compounds of transition metals. We designed and synthesized a series of photoinduced, singlet oxygen-mediated donors of neurochemicals. Molecular constructs of the donors were based on 1,3-diphenylisoindole, in which neurochemicals were caged as parts of the isoindole units. The donors released biologically important neurochemicals, including phenethylamine (DPSY1), 4-aminopyridine (DPSY2), phenylethanolamine (DPSY3), and tyramine (DPSY4), upon visible light photoirradiation of a singlet oxygen sensitizer. The light-induced photolysis was monitored by employing 1H NMR and UV-vis absorption spectroscopic techniques. The combined spectroscopic investigations revealed that the photorelease involved the fast formation of an endoperoxide of the donor, followed by dissociation into 2-benzoylbenzophenone and neurochemicals. We envision that these photodonors will be useful in a variety of biological studies. |