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257354

Sigma-Aldrich

1-Pyrenebutyric acid

97%

Synonym(s):

4-(1-Pyrenyl)butyric acid, PyBA

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About This Item

Empirical Formula (Hill Notation):
C20H16O2
CAS Number:
3443-45-6
Molecular Weight:
288.34
Beilstein/REAXYS Number:
2140554
EC Number:
222-354-7
MDL number:
MFCD00004141
UNSPSC Code:
12352103
PubChem Substance ID:
24855581
NACRES:
NA.23

Quality Level

200

assay

97%

form

powder

mp

184-186 °C (lit.)

fluorescence

λex 341 nm; λem 376 nm in methanol
λex 342 nm; λem 395 nm (Reaction product)

SMILES string

OC(=O)CCCc1ccc2ccc3cccc4ccc1c2c34

InChI

1S/C20H16O2/c21-18(22)6-2-3-13-7-8-16-10-9-14-4-1-5-15-11-12-17(13)20(16)19(14)15/h1,4-5,7-12H,2-3,6H2,(H,21,22)

InChI key

QXYRRCOJHNZVDJ-UHFFFAOYSA-N

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General description

1-Pyrenebutyric acid (PBA) is a conjugated polymer that has a large π system and a carboxylic group. It is majorly used in surface functionalization. It has a high fluorescence efficiency and stability that make it useful in optoelectronic applications.

Application

PBA can be grafted on the surface of graphene and can be used in sensors. It can also be in the fabrication of ultracapacitor electrodes as alternative storage systems. It can also be used in the formation of multi-layered film for photovoltaic applications.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF6571
BCCD9860
BCCC0981
BCBZ4984
BCBV3629

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Peter Guterstam et al.
Biochimica et biophysica acta, 1788(12), 2509-2517 (2009-10-03)
Cell-penetrating peptides (CPPs) are membrane permeable vectors recognized for their intrinsic ability to gain access to the cell interior. The hydrophobic counter-anion, pyrenebutyrate, enhances cellular uptake of oligoarginine CPPs. To elucidate CPP uptake mechanisms, the effect of pyrenebutyrate on well-recognized
Ming-Yuan Wei et al.
Biosensors & bioelectronics, 24(9), 2909-2914 (2009-03-27)
A redox-labeled direct competitive electrochemical immunoassay for polycyclic aromatic hydrocarbons (PAHs) was developed. A ruthenium tris(bipyridine)-pyrenebutyric acid conjugate was synthesized as the redox-labeled tracer. Its recognition by an anti-PAH monoclonal antibody was confirmed by surface plasmon resonance. In the immunoassay
Yongzheng Yang et al.
Organic & biomolecular chemistry, 4(9), 1746-1754 (2006-04-25)
FRET-based fluorogenic substrates for lipases and esterases were prepared in four steps from commercially available building blocks. The substrates are pyrenebutyric acid monoesters of aliphatic 1,2-diols bearing a dinitrophenylamino group as a quencher. The most enzyme-reactive substrate is ester 2a.
Wei Song et al.
Biosensors & bioelectronics, 26(7), 3181-3186 (2011-01-25)
A highly efficient enzyme-based screen printed electrode (SPE) was obtained by using covalent attachment between 1-pyrenebutanoic acid, succinimidyl ester (PASE) adsorbing on the graphene oxide (GO) sheets and amines of tyrosinase-protected gold nanoparticles (Tyr-Au). Herein, the bi-functional molecule PASE was
On monolayer formation of pyrenebutyric acid on graphene
Hinnemo M, et al.
Langmuir, 33(15), 3588-3593 (2017)
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