Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Samples of halogenated BODIPY dyes in ambient lighting and fluorescing under UV
BODIPY is the technical common name of a chemical compound with formula C 9H 7BN 2F 2, whose molecule consists of a boron difluoride group BF 2 joined to a dipyrromethene group C 9H 7N 2; specifically, the compound 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene in the IUPAC nomenclature.[1] The common name is an abbreviation for "boron-dipyrromethene". It is a red crystalline solid, stable at ambient temperature, soluble in methanol.[1]
The compound itself was isolated only in 2009,[2][1][3] but many derivatives—formally obtained by replacing one or more hydrogen atoms by other functional groups—have been known since 1968, and comprise the important class of BODIPY dyes.[4] These organoboron compounds have attracted much interest as fluorescent dyes and markers in biological research.[1]
^ abcdefgK. Tram; H. Yan; H. A. Jenkins; S. Vassiliev; D. Bruce (2009). "The synthesis and crystal structure of unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)". Dyes and Pigments. 82 (3): 392–395. doi:10.1016/j.dyepig.2009.03.001.
^A. Schmitt; B. Hinkeldey; M. Wild; G. Jung (2009). "Synthesis of the Core Compound of the BODIPY Dye Class: 4,4′-Difluoro-4-bora-(3a,4a)-diaza-s-indacene". J. Fluoresc. 19 (4): 755–759. doi:10.1007/s10895-008-0446-7. PMID 19067126. S2CID 7012021.
^I. J. Arroyo; R. Hu; G. Merino; B. Z. Tang; E. Peña-Cabrera (2009). "The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System". J. Org. Chem. 74 (15): 5719–22. doi:10.1021/jo901014w. PMID 19572588.
^Alfred Treibs und Franz-Heinrich Kreuzer. Difluorboryl-Komplexe von Di- und Tripyrrylmethenen. Justus Liebigs Annalen der Chemie 1968, 718 (1): 208-223. doi: 10.1002/jlac.19687180119
BODIPY is the technical common name of a chemical compound with formula C 9H 7BN 2F 2, whose molecule consists of a boron difluoride group BF 2 joined...
derivatives: porphin, phthalocyanine, bilirubin Dipyrromethene derivatives: BODIPY, aza-BODIPY These fluorophores fluoresce due to delocalized electrons which can...
rearrangement to form benzamide, catalyzed by nickel salts or photocatalyzed by BODIPY. Its dehydration yields benzonitrile. It can be hydrolyzed to regenerate...
intensity image, Phasor image and the unmixed results for a cell transfected with DAPI,BODIPY and texas red shown by blue, green and red respectively....
O-vinylketoxime. The N-vinyl product was then used in the synthesis of a new BODIPY. In 2005 a version of the Trofimov reaction was reported where both the...
degradation of Hif-1α. Cadmium-selective sensors based on the fluorophore BODIPY have been developed for imaging and sensing of cadmium in cells. One powerful...
"Nonradiative Decay Channels for a Structurally-Distorted, Monostrapped BODIPY Derivative". The Journal of Physical Chemistry A. 122 (47): 9160–9170. Bibcode:2018JPCA...
boron-containing compounds that have been linked to porphyrin are BODIPY and diketonate. The BODIPY chromophore acts as an antenna: it absorbs a broad range of...
challenging. Such a function is called integrated logic and is exemplified by the BODIPY-based, half-subtractor logic gate illustrated by Coskun, Akkaya, and their...
-> {RC(O)-H}+ Pd^0}}} In a variation of the Fukuyama reduction the core BODIPY molecule has been synthesized from the SMe-substituted derivative: Additional...
motif that binds to Cu(I) causing the excitation of a boron-dipyrromethene (BODIPY) dye in the visible region. The probe has good selectivity for Cu(I) over...
Dziuba D, Jurkiewicz P, Cebecauer M, Hof M, Hocek M (2016). "A Rotational BODIPY Nucleotide: An Environment-Sensitive Fluorescence-Lifetime Probe for DNA...
to fluorophores such as fluorescein, Alexa Fluor 488, Oregon Green, and BODIPY FL. Takashi, R; Duke, J; Ue, K; Morales, M.F (1976). "Defining the "fast-reacting"...
Metal–Organic Frameworks (MOFs): Efficient Strut-to-Strut Energy Transfer in Bodipy and Porphyrin-Based MOFs". Journal of the American Chemical Society. 133...
azobenzene and diarylethenes or photocages such as o-nitrobenzyl, coumarin, and BODIPY compounds into the pharmacophore. This selective activation of the biomolecules...
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