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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.
Pyrromethene-HEMA-based photopolymerizable holographic recording material
Blaya S, et al.
Optics Communications, 228(1-3), 55-61 (2003)
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)
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)
Daminda Navarathne et al.
Chemical communications (Cambridge, England), 47(44), 12125-12127 (2011-10-15)
An efficient cascade FRET was realized in solid state DNA-CTMA thin films using a three chromophore system without any covalent attachments. The extent of energy transfer from Cm102 to SRh was studied and found to improve eight-fold using the bridging
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