A sensitive and selective chemiluminogenic probe for palladium

Palladium triggered removal of a propargyl group leads to the cleavage of the 1,2-dioxetane ring, leading to bright chemiluminescence. The reaction of the probe is highly specific for the Pd species, thus the probe described here has considerable potential for practical utility. © The Royal Society of Chemistry.2015

Thinking outside the silicon box: Molecular and logic as an additional layer of selectivity in singlet oxygen generation for photodynamic therapy

A simple derivative of a well-known dye bodipy appears to be a satisfactory sensitizer for singlet oxygen. Moreover, the rate of singlet oxygen generation can be modulated by two cancer-related cellular parameters, sodium ion concentration and acidity. Singlet oxygen generation rate is maximal when sodium ions and an organic acid were added. The operation of this molecular automaton follows AND logic, which introduces an additional layer of selectivity in the photodynamic action of the reagent. It should also be noted that in this system sensing, computing and actuating functions are realized within a single molecule. Copyright © 2008 American Chemical Society

Chemiluminescence sensing of fluoride ions using a self-immolative amplifier

An enhanced chemiluminescence signal is obtained when electronically triggered dioxetane cleavage is initiated by fluoride-mediated deprotection of the silyl-protecting group, followed by self-immolation via 1,4-quinone-methide rearrangement. The reaction takes place even when the probe is trapped within a PMMA layer on top of a glass plate. In that arrangement, fluoride in aqueous solutions can be detected selectively at low micromolar concentrations. © 2014 American Chemical Society

Reaction-based BODIPY probes for selective bio-imaging

Complex intracellular environment of cells, which involves interaction of a large variety of bio-molecules, is a dynamic medium with full of important information that can be recovered as well as many unanswered questions. It is highly critical to image and track biologically relevant molecules in their native media without interfering with the regular cellular processes in order to gather as much data as possible to illuminate intricacies of the biological mechanisms. To that end, small-molecule fluorescent probes have been extensively developed during the last few decades with the help of current advances in imaging technologies. Although conventional probes utilizing non-covalent supramolecular interactions with the analyte of interest are successful, significant effort has been also put into the design of reaction-based probes (chemodosimeters). Chemodosimeters exploit selective reactions of analytes with fluorophores in attempt to improve the selectivity of the probes, address the limitations of former sensors and broaden the palette of useful probes. Various types of fluorophore scaffolds can be used in the design of chemodosimeters for visualization of different analytes. In this review, we highlight the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) based chemodosimeters which have been used to image bio-thiols, reactive oxygen/nitrogen species, and gaseous molecules in living cells. © 2017 Elsevier B.V

Toward singlet oxygen delivery at a measured rate: A self-reporting photosensitizer

A Bodipy-based energy transfer cassette with a singlet oxygen reactive linker between the donor and acceptor modules has an interesting emergent property, if the acceptor module is also a photosensitizer. Singlet oxygen produced by the photosensitizer reacts rapidly with the molecule itself to liberate the energy donor, resulting in an enhanced fluorescence emission. The result is a self-reporting photosensitizer providing an assessment of the singlet oxygen production rate under the operational conditions. © 2014 American Chemical Society

Near IR excitation of heavy atom free Bodipy photosensitizers through the intermediacy of upconverting nanoparticles

Orthogonal dimers of Bodipy were recently shown to be efficient generators of singlet oxygen. However, these dyes require green light for excitation, which would be very quickly attenuated inside the mammalian tissues. We now demonstrate that when these dyes are covalently attached to UCNPs, near IR irradiation results in very efficient generation of singlet oxygen. This journal is © the Partner Organisations 2014

Novel molecular building blocks based on the boradiazaindacene chromophore: Applications in fluorescent metallosupramolecular coordination polymers

We designed and synthesized novel boradiazaindacene (Bodipy) derivatives that are appropriately functionalized for metal-ion-mediated supramolecular polymerization. Thus, ligands for 2-terpyridyl-, 2,6-terpyridyl-, and bipyridyl-functionalized Bodipy dyes were synthesized through Sonogashira couplings. These fluorescent building blocks are responsive to metal ions in a stoichiometry-dependent manner. Octahedral coordinating metal ions such as Zn II result in polymerization at a stoichiometry corresponding to two terpyridyl ligands to one Zn II ion. However, at increased metal ion concentrations, the dynamic equilibria are re-established in such a way that the monomeric metal complex dominates. The position of equilibria can easily be monitored by 1H NMR and fluorescence spectroscopies. As expected, although open-shell Fe II ions form similar complex structures, these cations quench the fluorescence emission of all four functionalized Bodipy ligands. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA

A sensitive and selective ratiometric near IR fluorescent probe for zinc ions based on the distyryl-bodipy fluorophore

(Chemical Equation Presented) A novel distyryl-substituted boradiazaindacene (bodipy) dye with an emission peak moving hypsochromically from 730 to 680 nm on Zn(II) ion binding seems to be promising as one of the very few water-soluble fluorescent chemosensors emitting in the near IR region. © 2008 American Chemical Society

Molecular Logic: From Single Logic Gates to Sophisticated Logic Circuits, from Fundamental Science to Practical Applications

[No abstract available

Selective Hg(II) sensing with improved stokes shift by coupling the internal charge transfer process to excitation energy transfer

Versatile chemistry of the Bodipy chromophore allows modular assembly of an excitation energy donor, acceptor, and a cation selective ligand in just a couple of steps. The new approach should be applicable in other designs which target molecular sensors with large Stokes shifts and red to near IR emission. © 2010 American Chemical Society