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 Organic sensitizing dyes


The interest in organic sensitizing dyes for usage in DSSCs has been growing quickly the past few years. It was initiated for reasons such as non-limited feedstock, improved prerequisites for scalability, recycling issues, economy on a large-scale . This interest was strengthened after the CMD results from Feldt et al. in J. Am. Chem. Soc., 2010, 132 (46), pp 16714–16724, where organic dyes in combination with a cobalt polypyridine-based one-electron redox mediator improved the performance of liquid DSSC devices. The past few years, it has been shown that organic dyes can also provide stability advantages in relation to metal-organic dyes also in iodide/triiodide electrolyte systems. In addition, the possibility to realize well-performing DSSC dyes in different colors have further increased the interest for organic dyes. Dyenamo offers a number of organic broad-spectrum absorbing dyes, two organic infra-red absorbing dyes and one organic p-type dye. In order to obtain quotations, please proceed via "Select amount for quotation" in the product descriptions. For larger amounts than the ones displayed, please contact us.


Overview

Product code Name Approximate color* λabs,max (nm)
DN-F01 Dyenamo Yellow 378 (deprotonated)
DN-FP01 P1 468
DN-F04M D45 471 (EtOH)
DN-F03 D5 476
DN-F02 L1 404 (deprotonated)
DN-F04 Dyenamo Orange 500
DN-F05M D51 505 (EtOH)
DN-F05Y Y123 530
DN-F05 Dyenamo Red 541
DN-F16 XY1 552 (DCM)
DN-F16B XY1b 552 (DCM)
DN-F08 JF419 554 (DCM)
DN-F09 MKA253 554 (DCM)
DN-F10 Dyenamo Blue 584 (DCM)
DN-F10M Dyenamo Blue 2016 584 (DCM)
DN-F17 R6 631 (DCM)
DN-F15 Dyenamo Transparent Green 703 (DMF)
DN-FI07 MK245 822

*The shown colors are just an illustration of the dye's appearance. The actual color of a device depends on various factors such as electrolyte, substrate, concentration of the dye and others.

DN-F-series: Broad-spectrum organic dyes

DN-FI-series: Near-infrared organic dyes

DN-FP series: P-type dye




DN-F-Series

DN-F17

R6



R6
Description:
The R6 dye combines state-of-the-art DSSC performance with an aesthetically appealing sapphire blue color. Power conversion efficiencies of 12.6% under AM1.5G conditions have been demonstrated using Co(bpy)3 as the redox mediator (Click here to see our cobalt complexes). Its photostability has also been shown to be good with devices retaining >90% of their initial performance after 1000 h full sunlight soaking at 60 °C.

Full name:
4-(7-((15-(Bis(4-(hexyloxy)phenyl)amino)-9,9,19,19-tetrakis(4-hexylphenyl)-9,19-dihydrobenzo[1',10']phenanthro[3',4':4,5]thieno[3,2-b]benzo[1,10]phenanthro[3,4-d]thiophen-5-yl)ethynyl)benzo[c][1,2,5]thiadiazol-4-yl)benzoic acid

CAS number:
1980035-77-5

Typical properties:
E0X (THF) = -4.9 eV vs vacuum
λabs (THF) = 631 nm (8.18*104 M-1 cm-1)
MW = 1803.53 g/mol

References:

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DN-F16

XY1



Dye_XY1_small
Description:
The XY1 dye (DN-F16) offers further improved red-response and extinction coefficient in relation to D35 (Dyenamo Orange) and Dyenamo Red/Y123 (DN-F05/DN-F05Y) which it builds upon. Due to its D-A-π-A structure it maintains a relatively high oxidation potential, which together with its long alkyl side chains enables high performance with even the most demanding redox mediators. In ssDSSCs device efficiencies of 6.7% have been demonstrated.

Full name:
(E)-3-(4-(6-(7-(4-(bis(2',4'-bis((2-ethylhexyl)oxy)-[1,1'-biphenyl]-4-yl)amino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophen-2-yl)phenyl)-2-cyanoacrylic acid

CAS number:
1979161-98-2

Typical properties:
E0X (DCM) = 0.99 V vs NHE
λabs (DCM) = 552 nm (5.65*104 M-1 cm-1)
MW = 1616.38 g/mol

References:

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DN-F16B

XY1b




Dye_XY1b_small
Description:
XY1b (DN-F16B) is a Dyenamo-developed variant of XY1 (DN-F16) designed to deliver the performance of XY1 at lower cost. By keeping the core XY1 structure intact, the photo- and electrochemical properties of the two dyes are practically identical.

Full name:
(E)-3-(4-(6-(7-(4-(bis(2',4'-dibutoxy-[1,1'-biphenyl]-4-yl)amino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophen-2-yl)phenyl)-2-cyanoacrylic acid

Typical properties:
MW = 1391.94 g/mol

References:

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DN-F10

Dyenamo Blue



DN-F10_small
Description:
Dyenamo's in-house developed non-published organic blue dye for well-performing esthetic DSSC devices.

Full name:
(E)-3-(5-(4-(4-(5-(4-(bis(2',4'-dibutoxy-[1,1'-biphenyl]-4-yl)amino)phenyl)thiophen-2-yl)-2,5-bis(2-ethylhexyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)phenyl)furan-2-yl)-2-cyanoacrylic acid

Typical properties:
λ max (DCM) = 584 nm (49 000 M-1 cm-1)
λ max (TiO2) = 563 nm
MW = 1363.81 g/mol

Additional information
This product is covered by patents of EPFL, Switzerland. Please contact us or EPFL (http://tto.epfl.ch) for further information.

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DN-F10M

Dyenamo Blue 2016



DN-F10M_small
Description:
Dyenamo's second in-house developed organic blue dye for high-performance esthetic DSSC devices. Dyenamo's experience of DN-F10 and DN-F10M is that they deliver very similar DSSC device performance and stability. However, out of these two dyes, DN-F10M is more cost-efficient in production and thus offered at a lower price and in larger quantities.

Full name:
(E)-3-(5-(4-(4-(5-(4-(bis(2',4'-dibutoxy-[1,1'-biphenyl]-4-yl)amino)phenyl)thiophen-2-yl)-2,5-dioctyl-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)phenyl)furan-2-yl)-2-cyanoacrylic acid

Typical properties:
λ max (DCM) = 584 nm (49 000 M-1 cm-1)
λ max (TiO2) = 563 nm
MW = 1363.81 g/mol

Additional information:
This product is covered by patents of EPFL, Switzerland. Please contact us or EPFL (http://tto.epfl.ch) for further information.
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DN-F04

Dyenamo Orange




Dye_35_small
Description:
During 2012 and 2013, Dyenamo Orange (D35) has been established worldwide as a reference organic dye for DSSCs. Excellent device stability has been obtained both under light and after at least 1000 h storage in darkness at temperatures of 85°C. The absorption spectrum of D35 makes it interesting also for indoor application due to a good match with fluorescent light. Moreover, it has been concluded that Dyenamo Orange (D35) is an excellent choice for see-through DSSC devices, due to high performance, good stability (also at 85°C), and an attractive orange color.

Full name:
(E)-3-(5-(4-(bis(2',4'-dibutoxy-[1,1'-biphenyl]-4-yl)amino)phenyl)thiophen-2-yl)-2-cyanoacrylic acid

Alternative name:
D35

CAS number:
1197992-37-2

Typical properties:
E0 = 1.04 V vs. NHE
λ max = 500 nm (31 000 M-1cm-1)
λ em = 597 nm (ethanol)
λ em = 658 nm (dichloromethane)
E0-0 = 2.18 eV
MW = 863.11 g/mol

References:

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DN-F04M

D45



Dye_45_small
Description:
D45 is a variant of Dyenamo Orange (D35) designed for use with aqueous electrolytes. The shorter alkyl chains on the donor side decreases the hydrophobicity of the sensitized surface, which improves wetting of the electrode when used with polar electrolyte solvents. Additionally, the smaller size of D45 compared to D35 enables it to reach higher dye loadings which allows the use of thinner TiO2 films.

Full name:
(E)-3-(5-(4-(bis(2',4'-dimethoxy-[1,1'-biphenyl]-4-yl)amino)phenyl)thiophen-2-yl)-2-cyanoacrylic acid

CAS number:
1513578-55-6

Typical properties:
Eox(DCM) = 0.99 V vs NHE
λmax(EtOH) = 471 nm (33 500 M-1 cm-1)
MW = 694.80 g/mol

References:
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DN-F05

Dyenamo Red



Dye_35_small
Description:
The two dyes DN-F05 (Dyenamo Red, also known as D35CPDT) and DN-F05Y (Y123) offer improved red-response in relation to DN-F04 (D35). Dyenamo's experience of DN-F05 and DN-F05Y is that they deliver very similar DSSC device performance and stability. However, out of these two dyes, DN-F05 is more cost-efficient in production and thus offered at a lower price.

Full name:
3-{6-{4-[bis(2',4'-dibutyloxybiphenyl-4-yl)amino-]phenyl}-4,4-dihexyl-cyclopenta-[2,1-b:3,4-b']dithiophene-2-yl}-2-cyanoacrylic acid

Alternative name:
Dyenamo red, D35CPDT, LEG4

CAS number:
1346255-80-8

Typical properties:
E0 = 0.88 V vs NHE
λ max = 541 nm (49 000 M-1 cm-1)
λ em = 717 nm (dichloromethane)
MW = 1125.58 g/mol

References:
Additional information
This product is covered by patents of EPFL, Switzerland. Please contact us or EPFL (http://tto.epfl.ch) for further information.
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DN-F05M

D51




Dye_D51_small
Description:
D51 is a variant of Dyenamo Red (D35CPDT) designed for use with aqueous electrolytes. The shorter alkyl chains on the donor side decreases the hydrophobicity of the sensitized surface, which improves wetting of the electrode when used with polar electrolyte solvents.

Full name:
(E)-3-(6-(4-(bis(2',4'-dimethoxy-[1,1'-biphenyl]-4-yl)amino)phenyl)-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophen-2-yl)-2-cyanoacrylic acid

Alternative name:
D51

CAS number:
1513578-58-9

Typical properties:
Eox(DCM) = 0.95 V vs NHE
λmax(EtOH) = 505 nm (47 200 M-1 cm-1)
MW = 957.26 g/mol

References:
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DN-F05Y

Y123




Dye_Y123_small
Description:
The two dyes DN-F05 (Dyenamo Red, also known as D35CPDT) and DN-F05Y (Y123) offer improved red-response in relation to DN-F04 (D35). The Y123 dye has been used to obtain 10% solar cell efficiency (Energy Environ. Sci., 2011, 4, 492 4924. DOI: 10.1039/C1EE02389F). In addition, it has resulted in excellent device stability at high temperatures (Jian et al., Solar Energy Materials and Solar Cells (2013), DOI: 10.1016/j.solmat.2013.04.017).

Full name:
3-{6-{4-[bis(2',4'-dihexyloxybiphenyl-4-yl)amino-]phenyl}-4,4-dihexyl-cyclopenta-[2,1-b:3,4-b']dithiphene-2-yl}-2-cyanoacrylic acid

CAS number:
1312465-92-1

Typical properties:
E0 = 1.07 V vs NHE (dye adsorbed on TiO2, in acetonitrile)
λ max = 530 nm (48 000 M-1 cm-1)
MW = 1237.80 g/mol

Additional information
This product is covered by patents of EPFL, Switzerland. Please contact us or EPFL (http://tto.epfl.ch) for further information.

References:
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DN-F08

JF419




Dye_JF419_small
Description:
Organic dye with fluorene donor showing superior device efficiencies than previous organic dyes, including Y123 (see reference below).

Full name:
(E)-3-(6-(4-(bis(5,7-bis(hexyloxy)-9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophen-2-yl)-2-cyanoacrylic acid

CAS number:
1391735-57-1

Typical properties:
E0 = 0.85 V vs NHE
λ max (DCM) = 554 nm (47 500 M-1 cm-1)
E0-0 = 2.10 eV
MW = 1317.93 g/mol

Additional information
This product is covered by patents of EPFL, Switzerland. Please contact us or EPFL (http://tto.epfl.ch) for further information.

References:
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DN-F09

MKA253



Dye_JF419_small
Description:
The dye MKA253 is our improved version of JF419 with the hexyloxy substituents on the fluorene donor replaced by butoxy groups. Dyenamo's experience of MKA253 and JF419 is that they deliver very similar DSSC device performance and stability. However, out of these two dyes, MKA253 is more cost-efficient in production and thus offered at a lower price.

Full name:
(E)-3-(6-(4-(bis(5,7-dibutoxy-9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophen-2-yl)-2-cyanoacrylic acid

CAS number:
1649427-54-2

Typical properties:
E0 = 0.85 V vs NHE
λ max (DCM) = 554 nm (47 500 M-1 cm-1)
E0-0 = 2.10 eV
MW = 1205.71 g/mol

Additional information
This product is covered by patents of EPFL, Switzerland. Please contact us or EPFL (http://tto.epfl.ch) for further information.

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DN-F01

Dyenamo Yellow





Dye_L0_small
Description:
The organic sensitizers DN-F01 (Dyenamo Yellow) to DN-F03 (D5) form a series of dyes with increasing conjugated π bridge. Among these three, the DN-F01 is the simplest donor-acceptor dye with high oxidation potential.

Full name:
4-(diphenylamino)phenylcyanoacrylic acid

Alternative name:
L0

CAS number:
30388-31-9

Typical properties:
E0 = 1.37 V vs. NHE
λ max (deprotonated)= 378 nm (36 000 M-1cm-1)
λ em = 507 nm (deprotonated, acetonitrile)
E0-0 = 2.9 eV
MW = 340.37 g/mol

References:
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DN-F02

L1




Dye_L1_small
Description:
The organic sensitizers DN-F01 (Dyenamo Yellow) to DN-F03 (D5) form a series of dye with increasing conjugated π bridge.

Full name:
5-[4-(diphenylamino)phenyl]thiophene-2-cyanoacrylic acid

CAS number:
762269-56-7

Typical properties:
E0 = 1.21 V vs. NHE
λ max (deprotonated) = 404 nm (25 000 M-1cm-1)
λ em = 548 nm (deprotonated, acetonitrile)
E0-0 = 2.64 eV
MW = 422.50 g/mol

References:
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DN-F03

D5




Dye_D5_small
Description:
The organic sensitizers DN-F01 (Dyenamo Yellow) to DN-F03 (D5) form a series of dye with increasing conjugated π bridge. Among these three, D5 is the more efficient organic dye.

Full name:
3-(5-(4-(diphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid

Alternative name:
L2

CAS number:
900182-08-3

Typical properties:
E0 = 1.08 V vs. NHE
λ max = 476 nm (38 000 M-1cm-1)
λ em = 594 nm (deprotonated, acetonitrile)
λ em = 625 nm (acetonitrile)
E0-0 = 2.25 eV
MW = 448.54 g/mol

References:
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DN-FI-Series

DN-FI07

MK245




Dye_dnfi07_small
Description:
The dye MK245 is an organic dye for near infrared sensitization.

Full name:
3-(2-((E)-2-((E)-3-((Z)-2-(3-(2-carboxyethyl)-1,1-dimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)ethylidene)-2-chlorocyclohex-1-en-1-yl)vinyl)-1,1-dimethyl-1H-benzo[e]indol-3-ium-3-yl)propanoate

CAS number:
193208-79-6

Typical properties:
E0 = 0.88 V vs. NHE
λ max = 822nm (146 000 M-1cm-1)
E0-0 = 1.38 eV
MW = 699.29 g/mol

References:
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DN-F15

Dyenamo Transparent Green




DN-F15_Small
Description:
Dyenamo Transparent Green is a vividly green squaraine dye with good stability in DSSCs.

Full name:
(3Z,4Z)-4-((5-carboxy-3,3-dimethyl-1-octyl-3H-indol-1-ium-2-yl)methylene)-2-(((E)-5-carboxy-3,3-dimethyl-1-octylindolin-2-ylidene)methyl)-3-(1-cyano-2-ethoxy-2-oxoethylidene)cyclobut-1-en-1-olate

Alternative name:
HSQ4

CAS number:
1613706-91-4

Typical properties:
EOX (DMF) = 0.74 V vs NHE
λabs (DMF) = 703 nm (1,37⋅105 M-1 cm-1)
MW = 804.04 g/mol

References:
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DN-FP-Series

DN-FP01

P1




P1
Description:
The dye P1 is a so-called p-type dye developed for sensitization of NiO electrodes for usage in both solar cell and solar fuel devices.

Full name:
4-(Bis-{4-[5-(2,2-dicyano-vinyl)-thiophene-2-yl]-phenyl}-amino)-benzoic acid

CAS number:
1042718-56-8

Typical properties:
HOMO: 1.38 V vs. NHE
LUMO: -0.87 vs. NHE
λ max = 468 nm (58 000 M-1cm-1)
MW = 605.69 g/mol

References:
  • P. Qin et al, J. Am. Chem. Soc. 2008, 130, 8570
  • P. Qin et al, Adv. Mater., 2009, 21, 2993
  • L. Li et al, Adv. Mater., 2010, 22, 1759
  • H. Krysova et al, PCCP, 2016,18, 16444-16450, DOI: 10.1039/C6CP02209J

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