Cyanide sensing via metal ion removal from a fluorogenic BODIPY complex

Cataloged from PDF version of article.We report a highly selective and sensitive reversible cyanide sensor operating in the ‘turn-off-on’ mode via decomplexation of Cu(II) ions from a brightly fluorescent boradiazaindacene derivative. The sensor is reversible as the emission signal originates from the dynamic equilibration of dipicolylamine–Cu(II) and tetracyanocuprate complex ions

Tetrastyryl-BODIPY-Based Dendritic Light Harvester and Estimation of Energy Transfer Efficiency

Cataloged from PDF version of article.Versatile BODIPY dyes can be transformed into bright near-IR-emitting fluorophores by quadruple styryl substitutions. When clickable functionalities on the styryl moieties are inserted, an efficient synthesis of a light harvester is possible. In addition, clear spectral evidence is presented showing that, in dendritic light harvesters, calculations commonly based on quantum yield or emission lifetime changes of the donor are bound to yield large overestimations of energy transfer efficiency

Cyanide sensing via metal ion removal from a fluorogenic BODIPY complex

We report a highly selective and sensitive reversible cyanide sensor operating in the 'turn-off-on' mode via decomplexation of Cu(II) ions from a brightly fluorescent boradiazaindacene derivative. The sensor is reversible as the emission signal originates from the dynamic equilibration of dipicolylamine-Cu(II) and tetracyanocuprate complex ions. © 2009 Elsevier Ltd. All rights reserved

Tetrastyryl-BODIPY-based dendritic light harvester and estimation of energy transfer efficiency

Versatile BODIPY dyes can be transformed into bright near-IR-emitting fluorophores by quadruple styryl substitutions. When clickable functionalities on the styryl moieties are inserted, an efficient synthesis of a light harvester is possible. In addition, clear spectral evidence is presented showing that, in dendritic light harvesters, calculations commonly based on quantum yield or emission lifetime changes of the donor are bound to yield large overestimations of energy transfer efficiency. © 2012 American Chemical Society

Heteroleptic metallosupramolecular complexes of bodipy dyes as energy transfer cassettes

Bodipy dyes with integral phenanthroline and terpyridine units heteroleptically assemble in the presence of zinc(II) ions to form energy transfer cassettes. These discrete complexes exhibit an approach to modularly designed efficient energy transfer and light harvesting systems through metal ion coordination. © 2012 American Chemical Society

Autonomous shuttling driven by an oscillating reaction: Proof of principle in a cucurbit[7]uril-bodipy pseudorotaxane

A bipyridinium dication-substituted Bodipy fluorophore, with a terminal carboxylic acid function, provides two alternative stations for cucurbit[7]uril. Changing pH from basic to acidic results in shuttling of the cucurbit[7]uril from one station to another. In addition, this shuttling is accompanied by a change in the emissive properties of the Bodipy dye, which is only observed in the presence of cucurbit[7]uril. More striking, is a demonstration of autonomous shuttling of the pseudorotaxane system in an oscillating pH system. © 2013 American Chemical Society

Tetrastyryl-bodipy dyes: Convenient synthesis and characterization of elusive near IR fluorophores

1,3,5,7-Tetramethyl-Bodipy derivatives undergo Knoevenagel-type condensations with aromatic aldehydes to ultimately yield tetrastyryl-Bodipy derivatives. The resulting dyes absorb and emit strongly In the near IR. As the versatility of the Bodipy dyes are fully appreciated, these new tetrastyryl dyes are likely to be featured In a variety of functional supramolecular systems. © 2009 American Chemical Society

Reaction-based sensing of fluoride ions using built-in triggers for intramolecular charge transfer and photoinduced electron transfer

(Figure Presented) Two Bodipy derivatives with silyl-protected phenolic functionalities signal fluoride concentrations both In solution and in a poly(methyl methacrylate) matrix. The exact location of the "nascent" phenolate group is Important. If it Is at the meso position, photoinduced electron transfer is triggered; however, if It is In full conjugation via a styryl moiety to the Bodipy core, strong intramolecular charge transfer Is triggered, resulting In a large red shift in the absorbance peak. In either case, a selective methodology for fluoride sensing is the Invariable result. © 2010 American Chemical Society

Convergent synthesis and light harvesting properties of dendritic boradiazaindacene (BODIPY) appended perylenediimide dyes

A convergent synthesis methodology, together with "click- chemistry" between azides and terminal alkynes, allows straighforward access to dendritic light harvesting systems. The novel dendrimer reported in this study has eight boradiazaindacene (BODIPY) units at the periphery and a perylenediimide (PDI) dye at the core. We have demonstrated that visible light is effectively collected as a result of the large absorption cross section of the dendrimer and efficiently channeled to the core PDI unit, resulting in a significant antenna effect. While being one of the very few energy transfer systems with a BODIPY and PDI chromophore pair, this novel dendritic molecule is one of the most efficient in light harvesting. The factors that may play important roles as the generation number increases also become apparent when emission characteristics were analyzed in comparison with a lower generation dendrimer. © 2010 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique

Selective manipulation of ICT and PET processes in styryl-bodipy derivatives: Applications in molecular logic and fluorescence sensing of metal ions

Remarkably versatile chemistry of Bodipy dyes allows the design and straightforward synthesis of multivalent-multitopic derivatives, which, with judicious selection of metal ion-ligand pairs based on known affinities, affords control and manipulation of photoinduced electron transfer and internal charge transfer processes as desired. We have demonstrated that metal ions acting as modulators (or inputs, in digital design parlance) can generate absorbance changes in accordance with the operation of a half-adder. In addition, an AND logic gate in the emission mode was delivered using a different binucleating arrangement of ligands. A molecular equivalent of a three-input AND logic gate was also obtained exploiting differential binding affinities of metal ions for different ligands. The results suggest that different metal ions can be used as nonannihilating inputs, selectively targeting various ligands incorporated within a single fluorophore, and with careful design, diverse photophysical processes can be selectively modulated, resulting in a range of signals, useful in molecular logic design, and offering an enticing potential for multianalyte chemosensors. © 2010 American Chemical Society