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757268

Sigma-Aldrich

2,4-Bis[4-(N,N-dibenzylamino)-2,6-dihydroxyphenyl]squaraine

97%

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About This Item

Empirical Formula (Hill Notation):
C44H36N2O6
Molecular Weight:
688.77
UNSPSC Code:
12352103
PubChem Substance ID:
329766661
NACRES:
NA.23

assay

97%

form

powder

λmax

640-646 nm in chloroform

SMILES string

Oc1cc(cc(O)c1[C]2[C+]([O-])[C]([C+]2[O-])c3c(O)cc(cc3O)N(Cc4ccccc4)Cc5ccccc5)N(Cc6ccccc6)Cc7ccccc7

InChI

1S/C44H36N2O6/c47-35-21-33(45(25-29-13-5-1-6-14-29)26-30-15-7-2-8-16-30)22-36(48)39(35)41-43(51)42(44(41)52)40-37(49)23-34(24-38(40)50)46(27-31-17-9-3-10-18-31)28-32-19-11-4-12-20-32/h1-24,47-50H,25-28H2

InChI key

OPBFFKVKPVVANS-UHFFFAOYSA-N

General description

2,4-Bis[4-(N,N-dibenzylamino)-2,6-dihydroxyphenyl] squaraine is used as an electron donor in solution processed organic photovoltaic (OPV) cells. [1] This molecule increases the power conversion efficiency (PCE) of OPVs because it can harvest more photons in the low-energy range and also increases exciton dissociation, energy transfer and charge carrier transport in ternary blend films in bulk heterojunction polymer solar cells.[2]

Application

Used as a donor material in both vacuum-deposited and solution-processed OPVs.[3]

Features and Benefits

  • Can be dissolved and solution processed and high extinction coefficient. [1]
  • Intense absorption in the red/near-IR regions.[4]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBK1365V

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High efficiency organic photovoltaic cells based on a vapor deposited squaraine donor
Siyi W.; et al.
Applied Physics Letters (2009)
Highly Absorbing Squaraines and Their Application to Organic Photovoltaics
Siyi Wang,Mark E. Thompson,and Kanth V.B. Josyula.
Material Matters, 7(1), 9-9 (2012)
Efficient far red sensitization of nanocrystalline TiO2 films by an unsymmetrical squaraine dye.
Jun-Ho Yum et al.
Journal of the American Chemical Society, 129(34), 10320-10321 (2007-08-04)
Improved Efficiency of Bulk Heterojunction Polymer Solar Cells by Doping Low Bandgap Small Molecule
An, Q., Zhang, F., Li, L., Wang, J., Zhang, J., Zhou, L., & Tang, W.
ACS Applied Materials & Interfaces (2014)
Optical and electrical properties of a squaraine dye in photovoltaic cells.
Chen, G., Yokoyama, D., Sasabe, H., Hong, Z., Yang, Y., & Kido, J.
Applied Physics Letters, 101(8), 083904 - 083904(4) (2012)

Articles

Development of Small Molecule Donors for Solution-Processed Organic Solar Cells

Solution-processed organic photovoltaic devices (OPVs) have emerged as a promising clean energy generating technology due to their ease of fabrication, potential to enable low-cost manufacturing via printing or coating techniques, and ability to be incorporated onto light weight, flexible substrates.

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