4-4-difluoro-4-bora-3a-4a-diaza-s-indacene and boron-difluoride

An unsymmetrical guanidine-cyclopropenimine proton sponge DAGUN and the related BF

Topics: Boron Compounds; Fluorescent Dyes; Guanidines; Hydrogen Bonding; Ionophores; Protons

Topics: Boron Compounds; Crystallography, X-Ray; Dioxoles; Fluorescence; Fluorescent Dyes; Models, Molecular; Molecular Structure

Oxasmaragdyrin (osm), a 22-π electron aromatic macrocycle containing four pyrroles and a furan ring connected by three methine bridges and two direct bonds is shown to be an excellent electron donor-sensitizer exhibiting adequate spectral and redox properties. Further, this novel heterocyclic macromolecule has been utilized in building donor-acceptor systems involving BF

Topics: Boron Compounds; Crystallography, X-Ray; Electrochemical Techniques; Macrocyclic Compounds; Magnetic Resonance Spectroscopy; Molecular Conformation; Pyrroles; Quantum Theory; Solvents; Spectrometry, Fluorescence; Thermodynamics

A novel AIE-active boron difluoride fluorescent probe P3T was designed and synthesized. P3T exhibited high sensitivity to intra- and extra-cellular pH changes. Furthermore, a Förster resonance energy transfer (FRET) system was constructed, where P3T acted as a donor fluorophore and DOX as the acceptor.

Topics: Boron Compounds; Fluorescence Resonance Energy Transfer; Fluorescent Dyes; Hydrogen-Ion Concentration; Limit of Detection; Microscopy, Electron, Transmission

Attempts to make a diamino disulfonic acid derivative of an aza-BODIPY showed it was difficult to add BF2 to a disulfonated azadipyrromethene, and sulfonation of an aza-BODIPY resulted in loss of the BF2 fragment. We conclude the electron-deficient character of aza-BODIPY dyes destabilizes them relative to BODIPY dyes. Consequently, sulfonation of the aza-BODIPY core is not a viable strategy to increase water solubility. This assertion was indirectly supported via stability studies of a BODIPY and an aza-BODIPY in aqueous media. To afford the desired compound type, an aza-BODIPY with two amino and two sulfonic acid groups was prepared via modification of the aryl substituents with cysteic acid.

Topics: Animals; Aza Compounds; Boron Compounds; Cell Line, Tumor; Cysteic Acid; Fluorescent Dyes; Hydrophobic and Hydrophilic Interactions; Mice; Microscopy, Fluorescence; Sulfonic Acids; Water

Evaluation of three subclasses of boron difluoride formazanate complexes bearing o-, m-, and p-anisole N-aryl substituents (Ar) as readily accessible alternatives to boron dipyrromethene (BODIPY) dyes for cell imaging applications is described. While the wavelengths of maximum absorption (λmax ) and emission (λem ) observed for each subclass of complexes, which differed by their carbon-bound substituents (R), were similar, the emission quantum yields for 7 a-c (R=cyano) were enhanced relative to 8 a-c (R=nitro) and 9 a-c (R=phenyl). Complexes 7 a-c and 8 a-c were also significantly easier to reduce electrochemically to their radical anion and dianion forms compared to 9 a-c. Within each subclass, the o-substituted derivatives were more difficult to reduce, had shorter λmax and λem , and lower emission quantum yields than the p-substituted analogues as a result of sterically driven twisting of the N-aryl substituents and a decrease in the degree of π-conjugation. The m-substituted complexes were the least difficult to reduce and possessed intermediate λmax , λem , and quantum yields. The complexes studied also exhibited large Stokes shifts (82-152 nm, 2143-5483 cm(-1) ). Finally, the utility of complex 7 c (Ar=p-anisole, R=cyano), which can be prepared for just a few dollars per gram, for fluorescence cell imaging was demonstrated. The use of 7 c and 4',6-diamino-2-phenylindole (DAPI) allowed for simultaneous imaging of the cytoplasm and nucleus of mouse fibroblast cells.

Topics: Anisoles; Boron Compounds; Crystallography, X-Ray; Diagnostic Imaging; Diamines; Fibroblasts; Fluorescence; Indoles; Models, Molecular; Molecular Structure; Porphobilinogen