Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties

Balandier, Jean‐Yves; Quist, Florence; Amato, Claire; Bouzakraoui, Saïd; Cornil, Jérôme; Sergeyev, Sergey; Geerts, Yves

doi:10.1016/j.tet.2010.09.086

Cited by 20 publications

(16 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Monomers M12-M15 were prepared according to literatures. [1][2][3][4] Iridium-catalyzed direct tetraborylation of 4,8-di(thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene was carried out to synthesize monomer DBD according to our previous procedure. 5,6 Solid-state 13 C-NMR spectra were recorded on a Bruker DRX-500 spectrometer.…”

mentioning

confidence: 99%

Donor–Acceptor Porous Conjugated Polymers for Photocatalytic Hydrogen Production: The Importance of Acceptor Comonomer

et al. 2016

View full text Add to dashboard Cite

Porous conjugated polymer (PCP) is a new kind of photocatalyst for photocatalytic hydrogen production (PHP). Here, we report the importance of the electronic properties of acceptor comonomer in determining the reactivity of 4,8-di(thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene (DBD)-based PCP photocatalyst for PHP application. It was found that the incorporation of nitrogen-containing ligand acceptor monomers into PCP network is an effective strategy to enhance the PHP activity. These moderately electron-deficient comonomers enhanced the dipole polarization effect. These PCPs exhibit appropriate solid-state morphology for charge transport. Powder X-ray diffraction (XRD) studies demonstrate that these PCP materials are semicrystalline materials. A strong correlation between the crystalline property and PHP activity is observed. The replacement of nitrogen-containing ligand acceptors with ligand-free strong acceptors is proved to be detrimental to the PHP process, indicating the proper choice in the electronic properties of monomer pair is important for achieving high photoactivity.

show abstract

mentioning

confidence: 99%

Donor–Acceptor Porous Conjugated Polymers for Photocatalytic Hydrogen Production: The Importance of Acceptor Comonomer

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The key monomer 7 was synthesized via three reaction steps, starting from DCT (compound 4), which is commercially available at relatively low cost. The generation of compound 5, starting from 4, was achieved by following the procedure previously reported 27. The Stille coupling between compound 5 and tributyl(4‐octylthiophen‐2‐yl)stannane generated compound 6, which was further treated with N ‐bromosuccinimide (NBS) to generate monomer 7, with good yield at each step.…”

Section: Resultsmentioning

confidence: 99%

“…The generation of compound 5, starting from 4, was achieved by following the procedure previously reported. [27] The Stille coupling between compound 5 and tributyl(4-octylthiophen-2-yl)stannane generated compound 6, which was further treated with N-bromosuccinimide (NBS) to generate monomer 7, with good yield at each step. The synthesis of monomer 3 involved similar Stille coupling and bromination, starting from 2,5-dibromothiophene.…”

Section: Polymer Design and Synthesismentioning

confidence: 99%

3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells

Zhang

Zhou

et al. 2020

Advanced Energy Materials

View full text Add to dashboard Cite

In this contribution, a versatile building block, 3,4‐dicyanothiophene (DCT), which possesses structural simplicity and synthetic accessibility for constructing high‐performance, low‐cost, wide‐bandgap conjugated polymers for use as donors in polymer solar cells (PSCs), is reported. A prototype polymer, PB3TCN‐C66, and its cyano‐free analogue polymer PB3T‐C66, are synthesized to evaluate the potential of using DCT in nonfullerene PSCs. A stronger aggregation property in solution, higher thermal transition temperatures with higher enthalpies, a larger dipole moment, higher relative dielectric constant, and more linear conformation are exhibited by PB3TCN‐C66. Solar cells employing IT‐4F as the electron acceptor offer power conversion efficiencies (PCEs) of 11.2% and 2.3% for PB3TCN‐C66 and PB3T‐C66, respectively. Morphological characterizations reveal that the PB3TCN‐C66:IT‐4F blend exhibits better π–π paracrystallinity, a contracted domain size, and higher phase purity, consistent with its higher molecular interaction parameter, derived from thermodynamic calculations. Moreover, PB3TCN‐C66 offers a higher open‐circuit voltage and reduced energy loss than most state‐of‐the‐art wide‐bandgap polymers, without the need of additional electron‐withdrawing substituents. Two additional polymers derived from DCT also demonstrate promising performance with a higher PCE of 13.4% being achieved. Thus, DCT represents a versatile and promising building block for constructing high‐performance, low‐cost, conjugated polymers for application in PSCs.

show abstract

“…[27][28] The target polymers PDPP3T-CN and PDPPTPT-CN were prepared via the Suzuki cross-coupling polymerization. The monomers were synthesized according to the procedures reported in literatures.…”

Section: Resultsmentioning

confidence: 99%

Nitrile-substituted thienyl and phenyl units as building blocks for high performance n-type polymer semiconductors

Xiong

Qiao

2015

Polym. Chem.

View full text Add to dashboard Cite

Two novel polymers PDPP3T-CN and PDPPTPT-CN containing nitrile-substituted thienyl and phenyl units were designed and synthesized. The influence of nitrile groups on the electronic properties and charge-carrier transport of the polymers was thoroughly investigated and highlighted by comparing with the corresponding non-nitrile substituted polymers. Experimental results showed the introduction of nitrile groups lowered the HOMO and LUMO energy levels of polymers about 0.3 eV and 0.2 eV, respectively. Thin film transistors characteristics displayed both polymers exhibited electrondominated ambipolar behavior in ambient condition. The highest electron/hole mobilities were 0.18/0.0083 cm 2 V -1 s -1 for PDPPTPT-CN and 0.09/0.0017 cm 2 V -1 s -1 for PDPP3T-CN, one of the highest electron mobility for DPP-based polymers measured in ambient condition with bottom-gate/top-contact device configuration.

show abstract

Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties

Cited by 20 publications

References 40 publications

Donor–Acceptor Porous Conjugated Polymers for Photocatalytic Hydrogen Production: The Importance of Acceptor Comonomer

Donor–Acceptor Porous Conjugated Polymers for Photocatalytic Hydrogen Production: The Importance of Acceptor Comonomer

3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells

Nitrile-substituted thienyl and phenyl units as building blocks for high performance n-type polymer semiconductors

Contact Info

Product

Resources

About