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Sigma-Aldrich

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

97%

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Empirical Formula (Hill Notation):
C32H44N2O6
Molecular Weight:
552.70
UNSPSC Code:
12352103
PubChem Substance ID:
329766735
NACRES:
NA.23

Assay

97%

form

solid

mp

295-305 °C

λmax

700 nm

Orbital energy

HOMO 5.3 eV 
LUMO 3.4 eV 

OPV Device Performance

ITO/MoO3/SQ:C70 (1:5)/BCP/Al

  • Short-circuit current density (Jsc): 13.7 mA/cm2
  • Open-circuit voltage (Voc): 0.87 V
  • Fill Factor (FF): 0.53
  • Power Conversion Efficiency (PCE): 6.3 %

ITO/NPD/SQ/C60/BCP/Al
  • Short-circuit current density (Jsc): 6.67 mA/cm2
  • Open-circuit voltage (Voc): 0.82 V
  • Fill Factor (FF): 0.55
  • Power Conversion Efficiency (PCE): 3 %

ITO/SQ/C60/BCP/Al
  • Short-circuit current density (Jsc): 7.13 mA/cm2
  • Open-circuit voltage (Voc): 0.75 V
  • Fill Factor (FF): 0.6
  • Power Conversion Efficiency (PCE): 3.2 %

SMILES string

CC(C)CN(CC(C)C)c1cc(O)c([C]2[C+]([O-])[C]([C+]2[O-])c3c(O)cc(cc3O)N(CC(C)C)CC(C)C)c(O)c1

InChI

1S/C32H44N2O6/c1-17(2)13-33(14-18(3)4)21-9-23(35)27(24(36)10-21)29-31(39)30(32(29)40)28-25(37)11-22(12-26(28)38)34(15-19(5)6)16-20(7)8/h9-12,17-20,35-38H,13-16H2,1-8H3

InChI key

JRHMFCJQZUVUIN-UHFFFAOYSA-N

General description

2,4-Bis[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl] squaraine (DIB-SQ) is used as an electron donor in solution processed photovoltaic cells.DIB-SQ increases the power conversion efficiency (PCE) because it can harvest more photons in the low-energy range and also increases excition dissociation, energy transfer and charge carrier transport in ternary blend films in bulk heterjunction polymer solar cells.

Application

This material is used as a donor material in vapor and solution processed organic heterojunction photovoltaic cells.

Features and Benefits

  • Can be dissolved and solution processed and has a high extinction coefficient.
  • Intense absorption in the red/near-IR regions.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Qiaoshi An et al.
ACS applied materials & interfaces, 6(9), 6537-6544 (2014-04-17)
We present performance improved ternary bulk heterojunction polymer solar cells by doping a small molecule, 2,4-bis[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl] squaraine (DIB-SQ), into the common binary blend of poly(3-hexylthiophene) (P3HT) and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). The optimized power conversion efficiency (PCE) of P3HT:PC71BM-based
Guo Chen et al.
Advanced materials (Deerfield Beach, Fla.), 24(20), 2768-2773 (2012-04-20)
High power conversion efficiencies of over 6.0% are achieved with a squaraine compound from co-deposited photovoltaic cells with a simple device structure, in which the efficiency is insensitive to blending ratios and thicknesses of photoactive layers. It demonstrates the huge
High efficiency organic photovoltaic cells based on a vapor deposited squaraine donor
Siyi Wang; Elizabeth I. Mayo; M. Dolores Perez; et al
Applied Physics Letters (2009)
Guodan Wei et al.
ACS nano, 6(1), 972-978 (2011-12-27)
We study a family of functionalized squaraine (fSQ) donors for absorbing in the near-infrared (NIR) and green spectral regions. The NIR-absorbing materials are the symmetric molecules 2,4-bis[4-(N-phenyl-1-naphthylamino)-2,6-dihydroxyphenyl]squaraine (1-NPSQ), 2,4-bis[4-(N,N-diphenylamino)-2,6 dihydroxyphenyl]squaraine, and 2,4-bis[4-(N,N-dipropylamino)-2,6-dihydroxyphenyl]squaraine. The green light absorbing donors are asymmetric squaraines
High efficiency organic photovoltaic cells based on a vapor deposited squaraine donor
Wang, S.; Mayo, E.; Perez M.; et al.
Applied Physics Letters, 94, 233304-233304 (2009)
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