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Sigma-Aldrich

Benzyl viologen dichloride

97%

Synonym(s):

1,1′-Dibenzyl-4,4′-bipyridinium dichloride

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About This Item

Empirical Formula (Hill Notation):
C24H22Cl2N2
CAS Number:
1102-19-8
Molecular Weight:
409.35
Beilstein:
3811585
EC Number:
214-158-5
MDL number:
MFCD00011991
UNSPSC Code:
12352103
PubChem Substance ID:
57648222
NACRES:
NA.23

Assay

97%

mp

260 °C (dec.) (lit.)

SMILES string

[Cl-].[Cl-].C(c1ccccc1)[n+]2ccc(cc2)-c3cc[n+](Cc4ccccc4)cc3

InChI

1S/C24H22N2.2ClH/c1-3-7-21(8-4-1)19-25-15-11-23(12-16-25)24-13-17-26(18-14-24)20-22-9-5-2-6-10-22;;/h1-18H,19-20H2;2*1H/q+2;;/p-2

InChI key

NLOIIDFMYPFJKP-UHFFFAOYSA-L

General description

Benzyl viologen dichloride (BVD) is an electrochromic indicator, which contains two chlorine atoms and an organic constituent attached with two nitrogen cations. In a redox reaction, BVD can be reduced in three states with different colors.

Application

BVD can be reduced to its neutral state by using sodium borohydride, which forms an n-type dopant for organic semiconductor based applications. It may be introduced to form a path for the transport of electrons from the thylakoid membranes to the mediator, which can be used in the fabrication of photo-driven bioanode. It also acts as a dopant with 2D layered materials to form an n-type chemical dopant that can be used to enhance the electrical properties of the triboelectric devices.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Interactions of benzyl viologen with surface-bound single-and double-stranded DNA.
Pang D and Abruna H
Analytical Chemistry, 72(19), 4700-4706 (2000)
Construction of photo-driven bioanodes using thylakoid membranes and multi-walled carbon nanotubes.
Takeuchi R, et al.
Bioelectrochemistry, 122(19), 158-163 (2018)
Triboelectric Series of 2D Layered Materials.
Seol M, et al.
Advanced Materials, 30(39), 1801210-1801210 (2018)
Benzyl viologen as an n-type dopant for organic semiconductors.
Huseynova G, et al.
Organic Electronics (2018)
Vayu Maini Rekdal et al.
Science (New York, N.Y.), 364(6445) (2019-06-15)
The human gut microbiota metabolizes the Parkinson's disease medication Levodopa (l-dopa), potentially reducing drug availability and causing side effects. However, the organisms, genes, and enzymes responsible for this activity in patients and their susceptibility to inhibition by host-targeted drugs are
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