An easy-to-synthesize Schiff base as a selective and colorimetric fluoride sensor via modulation of intramolecular charge transfer (ICT) has been demonstrated. A typical dual-ion binding property along with its distinct reversibility has been explored for YES, NOR and INH logic functions and a potential "Write-Read-Erase-Read" mimic.
Photoremovable protecting groups (PPGs) represent one of the main contemporary implementations of photochemistry in diverse fields of research and practical applications. For the past half century, organic and metal-complex PPGs were considered mutually exclusive classes, each of which provided unique sets of physical and chemical properties thanks to their distinctive structures. Here, we introduce the meso-methylporphyrin group as a prototype hybrid-class PPG that unites traditionally exclusive elements of organic and metal-complex PPGs within a single structure. We show that the porphyrin scaffold allows extensive modularity by functional separation of the metal-binding chromophore and up to four sites of leaving group release. The insertion of metal ions can be used to tune their spectroscopic, photochemical, and biological properties. We provide a detailed description of the photoreaction mechanism studied by steady-state and transient absorption spectroscopies and quantum-chemical calculations. Our approach applied herein could facilitate access to a hitherto untapped chemical space of potential PPG scaffolds.
A simple BODIPY-based small molecule has been identified to selectively label the endoplasmic reticulum for high-resolution imaging with negligible cytotoxicity.
A free-base and its Cu(III) derivative of bichromophoric meso-β linked corrole-BODIPY dyad were synthesized and structurally characterized by single crystal X-ray diffraction (XRD). Both corrole and BODIPY fragments maintained respective ground state electronic isolation despite their connection through a single bond due to a tilted orientation as observed by XRD. This was further supported by UV-vis and cyclic voltammetric studies. The Cu(III)-metalated dyad exhibits temperature-dependent paramagnetic behavior as observed in the variable temperature (1)H NMR due to the presence of a Cu(II)-corrole-π-cation radical. Importantly, the free-base exhibits complete fluorescence quenching probably due to photoinduced electron transfer to a low lying charge separated state. Interestingly, emission was regained upon addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) due to the deprotonation of corrole. The "turn on" fluorescence behavior and the presence of acidic NH protons were further exploited toward basic anion sensing utility.
Aromatic nucleophilic substitution (Ar-SN) reaction of 3,5-dibromopentafluorophenyl-BODIPY has been explored as a remarkable basis for selective discrimination of anions. The efficient and characteristic ability of anions to modulate the absorption and emission properties of the dye provides an instantaneous distinction through dual-modes. For the first time, a novel platform to achieve dual-modal and promising recognition with discrimination of a series of anions differing in the nucleophilic atoms (F, O, C and N) has been taken into consideration. The behaviour of various anions with dibromo-BODIPY and vivid signal transduction has been fully established with absorption and emission spectroscopy. In addition to this, recognition events have been unambiguously characterized by (1)H, (19)F-NMR and single-crystal XRD.
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