Beschreibung:
<jats:title>Abstract</jats:title><jats:p>We report the design, synthesis and evaluation of two novel photocages, NCARB and isoNCARB, belonging to the <jats:italic>o</jats:italic>‐nitrobenzyl chemotype and based on the carbazole ring system. The synthesis of each of these isomeric caging molecules was achieved in five steps and in 29 % overall yield, and their photochemical properties were evaluated using benzoic acid as a model for caging. In the event, upon irradiation at 400 nm for 60 min, 82 % and 42 % of benzoic acid was freed from the NCARB and isoNCARB photocages, respectively, whereas only 22 % was released from the nitrodibenzofuran (NDBF) cage. Moreover, the photochemical decaging efficiencies, ϵΦ, of the benzoates photocaged with NCARB and isoNCARB are about 150‐ and 20‐fold better, respectively, at 400 nm than the corresponding caged benzoate derived from NDBF. The water solubility of molecules caged with nitrocarbazole analogs was improved by <jats:italic>N</jats:italic>‐alkylation of NCARB, the better of the two new photocages, with an aminodicarboxylate group. This modified cage, NCARB‐DA, was exploited in the design of a caged fluoroquinolone antibiotic, the efficacy of which was illustrated in a bacterial growth inhibition assay, and a phenol‐caged tyrosine derivative.</jats:p>