BODIPY

BODIPY
BODIPY (unsubstituted)
Names
Preferred IUPAC name
5,5-Difluoro-5H-4λ5-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ylium-5-uide
Other names
Dipyrrometheneboron difluoride
Identifiers
3D model (JSmol)
8139995
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C9H7BF2N2/c11-10(12)13-5-1-3-8(13)7-9-4-2-6-14(9)10/h1-7H
    Key: GUHHEAYOTAJBPT-UHFFFAOYSA-N
  • [B-]1(N2C=CC=C2C=C3[N+]1=CC=C3)(F)F
Properties
C9H7BF2N2
Molar mass 191.98 g/mol
Appearance red crystalline solid[1]
Melting point 450 °C[1]
Solubility methanol, dichloromethane[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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]

  1. ^ a b c d e f g K. 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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