A star-shaped D–π–A small molecule based on a tris(2-methoxyphenyl)amine core for highly efficient solution-processed organic solar cells

Min, Jie; Luponosov, Yuriy N.; Solodukhin, Alexander N.; Kausch‐Busies, Nina; Ponomarenko, Sergei A.; Ameri, Tayebeh; Brabec, Christoph J.

doi:10.1039/c4tc01277a

Cited by 15 publications

(15 citation statements)

References 30 publications

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“…On the other hand, elongation of the alkyl chain results in the weakening of the intra-and intermolecular interactions in the solid state, which is in agreement with our previous results as well as the thermal properties of pristine oligomers. 34 A comparison of the hole-only mobility of N(Ph-OMe-2T-DCV-Me) 3 and N(Ph-OMe-3T-DCV-Hex) 3 to the values obtained for their full analogs with the TPA core 34 revealed a bit higher mobility for the blends based on the molecules with m-TPA core. These results regarding charge transport properties of blends will further influence the device performance as discussed below.…”

Section: Charge Transportmentioning

confidence: 99%

Section: Solubility and Thermal Propertiesmentioning

confidence: 99%

“…[15][16]34 N(Ph-3T-DCV-Hex) 3 , being the full analog of N(Ph-OMe-3T-DCV-Hex) 3 but with the TPA core, is characterized by a hexagonal columnar mesophase. 34 Meanwhile, N(Ph-2T-DCV) 3 and N(Ph-2T-DCV-Me) 3 can also be crystalline as received similar to their analogs with m-TPA core. Melting temperature and enthalpy in the pair of N(Ph-2T-DCV-Me) 3 and N(Ph-OMe-2T-DCV-Me) 3 are rather similar, while the melting temperature of N(Ph-2T-DCV) 3 is substantially higher than that of N(Ph-OMe-2T-DCV) 3 , albeit their melting enthalpies being also close to each other.…”

Section: Solubility and Thermal Propertiesmentioning

confidence: 99%

“…However, the first example of a D-A star-shaped molecule with alkoxy groups at TPA, namely with the tris(2-methoxyphenyl)amine (m-TPA) core, has been reported recently. 34 In this work we report on the synthesis and a comprehensive study of a series of four D-p-A oligomers having the tris-(2-methoxyphenyl)amine (m-TPA) core as a donor, either alkyl-DCV or DCV as acceptor units, and either bi-or terthiophene as p-bridges (Scheme 1). A comparison of properties of these four molecules with those of their full analogs with a TPA core [15][16][17]35 reveals the benefits and drawbacks of this chemical design strategy.…”

Section: Introductionmentioning

confidence: 99%

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Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

et al. 2016

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Synthesis of a series of star-shaped oligomers having a novel electron donating tris(2-methoxyphenyl)-amine (m-TPA) core, which is linked through a bithiophene or terthiophene p-bridge with electrondeficient alkyldicyanovinyl (alkyl-DCV) groups, is described. A comprehensive study of the oligomers revealed significant dependence of their physical properties, including absorption, molecular frontier energy levels, crystal packing, and melting and glass transition temperatures, upon the chemical structure. A comparison of their photophysical properties to the nearest analog having the common dicyanovinyl (DCV) groups demonstrated a number of benefits to use alkyl-DCV units for the design of donor-acceptor small molecules: higher solubility, increased electrochemical stability, better photovoltaic performance, and possibility to control the relative physical and photovoltaic properties by a simple adjustment of alkyl and p-bridge lengths. Modification of the well-known triphenylamine (TPA) core in the star-shaped oligomers by methoxy groups increases not only solubility, but also crystallinity of the oligomers, whereas their photovoltaic performance stays on a similar level as their analogs with a TPA core. The study demonstrates that these design strategies represent interesting and simple tools for the effective modulation of properties of star-shaped molecules.

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Section: Charge Transportmentioning

confidence: 99%

Section: Solubility and Thermal Propertiesmentioning

confidence: 99%

Section: Solubility and Thermal Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

et al. 2016

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“…17 Devices employing solution-processed small molecules as both donor and acceptor components gave device efficiencies of $3%, 18 which is similar to the average device performance of the widely studied and extensively optimized polymer : fullerene P3HT : PC60BM system. 19 As a result of this progress, a wide variety of new small molecules for solutionprocessed organic photovoltaics are being prepared, [20][21][22][23][24] including efficient donor-acceptor-donor (D-A-D) systems. 25 A recent electrochemical study of non-oxidised 4H-1,2,6-thiadiazines indicated electron affinities (LUMO energy values) of À3.25 to À3.66 eV with reversible oxidations and reductions.…”

Section: Introductionmentioning

confidence: 99%

4H-1,2,6-Thiadiazin-4-one-containing small molecule donors and additive effects on their performance in solution-processed organic solar cells

et al. 2015

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Effects of Alkyl Terminal Chains on Morphology, Charge Generation, Transport, and Recombination Mechanisms in Solution‐Processed Small Molecule Bulk Heterojunction Solar Cells

Min

Luponosov

Gasparini

et al. 2015

Advanced Energy Materials

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Length of the terminal alkyl chains at dicyanovinyl (DCV) groups of two dithienosilole (DTS) containing small molecules (DTS(Oct)2‐(2T‐DCV‐Me)2 and DTS(Oct)2‐(2T‐DCV‐Hex)2 ) is investigated to evaluate how this affects the molecular solubility and blend morphology as well as their performance in bulk heterojunction organic solar cells (OSCs). While the DTS(Oct)2‐(2T‐DCV‐Me)2 (a solubility of 5 mg mL−1) system exhibits both high short circuit current density (J sc) and high fill factor, the DTS(Oct)2‐(2T‐DCV‐Hex)2 (a solubility of 24 mg mL−1) system in contrast suffers from a poor blend morphology as examined by atomic force morphology and grazing incidence X‐ray scattering measurements, which limit the photovoltaic properties. The charge generation, transport, and recombination dynamics associated with the limited device performance are investigated for both systems. Nongeminate recombination losses in DTS(Oct)2‐(2T‐DCV‐Hex)2 system are demonstrated to be significant by combining space charge limited current analysis and light intensity dependence of current–voltage characteristics in combination with photogenerated charge carrier extraction by linearly increasing voltage and transient photovoltage measurements. DTS(Oct)2‐(2T‐DCV‐Me)2 in contrast performs nearly ideal with no evidence of nongeminate recombination, space charge effects, or mobility limitation. These results demonstrate the importance of alkyl chain engineering for solution‐processed OSCs based on small molecules as an essential design tool to overcome transport limitations.

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A star-shaped D–π–A small molecule based on a tris(2-methoxyphenyl)amine core for highly efficient solution-processed organic solar cells

Cited by 15 publications

References 30 publications

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

4H-1,2,6-Thiadiazin-4-one-containing small molecule donors and additive effects on their performance in solution-processed organic solar cells

Effects of Alkyl Terminal Chains on Morphology, Charge Generation, Transport, and Recombination Mechanisms in Solution‐Processed Small Molecule Bulk Heterojunction Solar Cells

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