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Sigma-Aldrich

Difluoro{3-ethyl-5-[1-(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl]-2,4-dimethyl-1H-pyrrolato-N}boron

98% (HPLC)

Synonym(s):

1,3,5,7,8-Pentamethyl-2,6-diethylpyrromethene-difluoroborate, 2,6-Diethyl-1,3,5,7,8-pentamethylpyrromethene-boron difluoride, 3-Ethyl-5-[1-(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)ethyl]-2,4-dimethyl-1H-pyrrole, boron complex, Exciton Pyrromethene 567, P 567, Pyrromethene 567

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About This Item

Empirical Formula (Hill Notation):
C18H25BF2N2
CAS Number:
131083-16-4
Molecular Weight:
318.21
UNSPSC Code:
12352103
PubChem Substance ID:
329765014
NACRES:
NA.23

Assay

98% (HPLC)

form

solid

mp

208-213 °C

fluorescence

λex 522 nm

SMILES string

CC(C1=C(C)C(CC)=C(C)N1B(F)2F)=C3[N]2=C(C)C(CC)=C3C

InChI

1S/C18H25BF2N2/c1-8-15-10(3)17-12(5)18-11(4)16(9-2)14(7)23(18)19(20,21)22(17)13(15)6/h8-9H2,1-7H3

InChI key

DZSMVBDAUBBZJD-UHFFFAOYSA-N

General description

Difluoro{3-ethyl-5-[1-(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl]-2,4-dimethyl-1H-pyrrolato-N}boron is a pyrromethene dye that is majorly used in liquid and solid state lasers. Its properties include low intersystem crossing and low triplet-triplet absorption which results in a high fluorescent quantum yields.

Application

BODIPY laser dyes are used to generate fluorescent conjugates of proteins; nucleotides; oligonucleotides and dextrans; and to prepare fluorescent enzyme substrates; fatty acids; phospholipids; lipopolysaccharides; receptor ligands and polystyrene microspheres.

Used for solid-state dye laser devices.
Difluoro{3-ethyl-5-[1-(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl]-2,4-dimethyl-1H-pyrrolato-N}boron can used in the fabrication of lasers for a variety of applications such as optoelectronics, and high intensity data storage.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Leonid M Goldenberg et al.
Advanced materials (Deerfield Beach, Fla.), 24(25), 3339-3343 (2012-06-01)
Distributed feedback (DFB) lasers are produced directly in fluorescent azobenzene-containing materials using a single holographic optical step. Surface relief grating capable of producing images in fluorescence microscopy can be holographically formed in a number of materials.
The concentration dependence of the normalized photostability of 1, 3, 5, 7, 8-pentamethyl-2, 6-di-t-butylpyrromethene-difluoroborate complex (PM-597) methanol solutions
Sisk WN and Sanders W
Journal of Photochemistry and Photobiology A: Chemistry, 167(2-3), 185-189 (2004)
Pyrromethene-HEMA-based photopolymerizable holographic recording material
Blaya S, et al.
Optics Communications, 228(1-3), 55-61 (2003)
Influence of plasmon resonance in silver nanoparticles on the properties of stimulated emission of 1, 3, 5, 7, 8-pentamethyl-2, 6-diethylpyrromethene-difluoroborate molecules in film of porous aluminum oxide
Ibrayev NK and Aimukhanov AK
Optics & Laser technology, 115(2-3), 246-250 (2019)
Alexander B Nepomnyashchii et al.
Accounts of chemical research, 45(11), 1844-1853 (2012-04-21)
BODIPY (boron dipyrromethene) dyes are unique materials with spectroscopic and electrochemical properties comparable to those of aromatic hydrocarbons. Electrochemical studies are useful in understanding the redox properties of these materials and finding structure-stability relations for the radical ions; along with
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