PDPP4T

Order Code: M331
MSDS sheet

Price

(excluding Taxes)

£188.30


PDPP4T is now available featuring:

  • High molecular weight, high purity and good solubility (PDPP4T is purified by soxhlet extraction with methanol, hexane and chlorobenzene under argon atmosphere)
  • Batch specific GPC data so you have confidence in what you are ordering and GPC data is always necessary for your publications
  • Now you can order larger quantity so you can plan your experiments with polymer from the same batch

Pricing

Batch Quantity Price
M331/M332 100 mg £188.3
M332 250 mg £399.6
M332 500 mg £719.2
M332 1 g £1294.6
M332 5 g / 10 g* Please enquire

 *for 5 - 10 grams order quantity, the lead time is 4-6 weeks.

Batch Details

Batch Mw Mn PDI
M331 89,700 48,950 1.83
M332 171,138 76,226 2.45

 

General Information

 

Full name Poly[2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione -3,6-diyl)-alt-(2,2’;5’,2’’;5’’,2’’’-quaterthiophen-5,5’’’-diyl)]
Synonyms
  • DPP-4T
  • DPP4T
  • pDPP
  • PDQT
CAS number 1267540-03-3
Chemical formula (C62H90N2O2S4)n
Molecular weight See Batch Details table above
HOMO / LUMO HOMO = -5.2 eV, LUMO = -4.0 eV [7]
Classification / Family Quaterthiophene, Heterocyclic five-membered ring, Organic semiconducting materials, Low band gap polymers, Organic photovoltaics, Polymer solar cells, OFETs
Chemical structure of PDPP4T. CAS number 1267540-03-3. Chemical structure (C62H90N2O2S4)n.

Characterisation

Soxhlet extraction was carried out using methanol, acetone, hexane and then chlorobenzene as washing solvents under argon. Chlorobenzene fraction was concentrated, precipitated with methanol, and dried under vacuum at 40 oC for 48 hours. GPC was carried out using 1,2,4-trichlorobenzene as eluent at 140 oC by using polystyrene as standards.

gpc-dpp4t-pdpp4t
Molecular weight distribution of PDPP4T chlorobenzene Soxhlet fraction from GPC analysis.

 

Applications

PDPP4T, also known as DPP4T, Poly[2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione -3,6-diyl)-alt-(2,2’;5’,2’’;5’’,2’’’-quaterthiophen-5,5’’’-diyl)] is a promising class of semiconducting polymers for organic solar cells. This is due to its small optical band gap and high charge-carrier mobility.

DPP4T has one DPP unit as electron-withdrawing and four five-membered thiophene as electron-rich units in its backbone, resulting a low-band gap polymer semiconductor with planar structure. The alkyl chain attached to DPP unit not only serves as a high-solubilising group, but also has a tendency to crystallise to ensure a better packing film. Due to its electron-rich and planar structure with the capacity of forming well-packed films, DPP4T has been reported exhibiting a hole mobility greater than 1 cmV-1 s-1 [8] in top-contact bottom-gate devices.

By using a solvent swelling assisted sequential deposition (SSA-SD) method to produce bulk heterojunction PSCs based on a crystalline diketopyrrolopyrrole (DPP) polymer and PC71BM, Device performance PCE of 7.59% with a VOC of 0.61 V, JSC of 17.95 mA/cm2 , and FF of 69.6%, is reported with PC71BM as electron acceptor [1]. Also by adding polymers like DPP-DTT with high mobility, device performance with higher PCE should be expected [5].

 

Synthetic Route

DPP4T was synthesised by using  3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and 5,5'-bis(trimethylstannyl)-2,2'-bithiophene as starting materials via Stille Coupling polymerisation in chlorobenzene. Targeted polymer was purified using Soxhlet extraction with methanol, acetone, hexane and finally chlorobenzene as washing and extracting solvents.

PDPP4T synthesis
PDPP4T synthesis via a Stille Coupling reaction with 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and 5,5-bis(trimethylstannyl)-2,2-bithiophene as starting materials.

 

Literature and Reviews

    1. Sequential Deposition: Optimization of Solvent Swelling for High-Performance Polymer Solar Cells, Y. Liu et al., ACS Appl. Mater. Interfaces, 7, 653-661 (2015)
    2. Copolymers of diketopyrrolopyrrole and thienothiophene for photovoltaic cells, J.C. Bijleveld et al., J. Mater. Chem., 21, 9224-9231 (2011)
    3. Diketopyrrolopyrrole-Based π‑Conjugated Copolymer Containing β‑Unsubstituted Quintetthiophene Unit: A Promising Material Exhibiting High Hole-Mobility for Organic Thin-Film Transistors, Z. Yi et al., Chem. Mater., 24, 4350-4356 (2012)
    4. Universal Correlation between Fibril Width and Quantum Efficiency in Diketopyrrolopyrrole-Based Polymer Solar Cells, W. Li, J. Am. Chem. Soc., 135, 18942−18948 (2013).
    5. Enhanced efficiency of polymer solar cells by adding a high-mobility conjugated polymer, S. Liu et al., Energy Environ. Sci., 8, 1463-1470 (2015)
    6. Efficient Polymer Solar Cells Based on a Low Bandgap Semi-crystalline DPP Polymer-PCBM Blends, F. Liu et al, Adv. Mater., 24, 3947–3951 (2012)

    7. Annealing-Free High-Mobility Diketopyrrolopyrrole−Quaterthiophene Copolymer for Solution-Processed Organic Thin Film Transistors, Y. Li et al., J. Am. Chem. Soc., 133, 2198–2204 (2011)

    8. 2,5-Bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-Based DonorAcceptor Alternating Copolymer Bearing 5,5’-Di (thiophen-2-yl)-2,20 -biselenophene Exhibiting 1.5 cm2V-1s-1Hole Mobility in Thin-Film Transistors,  J. S. Ha et al., J. Am. Chem. Soc. 133, 10364–10367 (2011).