The effect of alkylthio substituents on the photovoltaic properties of conjugated polymers

Li, Yang; Zhong, Yuancong; Jiang, Huanxiang; Rath, Thomas; Wang, Qian; Ehmann, Heike; Trimmel, Gregor; Wen, Shuguang; Zhang, Yong; Yang, Renqiang

doi:10.1016/j.orgel.2019.01.051

Cited by 7 publications

(9 citation statements)

References 49 publications

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“…Conformational locking can be achieved through a number of different chalcogen bonding interactions, such as S•••O, 100,138–141 S•••N, 142,143 S•••S, 144 and S•••F 145,146 interactions. These interactions can also be engineered through rationally designed building blocks, such as the benzodifurandione‐based oligo(phenylene‐vinylene) (BDOPV) derivatives designed by the Pei group 147,148 .…”

Section: Chalcogen Bondingmentioning

confidence: 99%

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Mullin

Sharber

Thomas

2021

Journal of Polymer Science

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Organic conjugated polymers and oligomers are key electronic materials for applications such as transistors, photovoltaics, and light emitting devices due to their potential for solution processability, mechanical flexibility, and precise structure-based tuning compared to inorganic materials. In dilute environments, the optoelectronic properties of conjugated polymers are largely governed by their constitutional structure and, to a lesser degree, their solution-state intramolecular configuration. In the solid state, intramolecular conformation and intermolecular electronic coupling impact these properties substantially, especially in relation to device performance. Therefore, an increasingly important area of research concerning conjugated materials is developing design strategies aimed at optimizing the solid-state packing for electronic applications. Programming solid-state packing arrangements through discrete non-covalent interactions is an emerging strategy within the context of conjugated polymers. This review focuses on the use of the two most prevalent discrete and directional interactions used to dictate the self-assembly of conjugated polymers and oligomers-hydrogen bonds and chalcogen bonds. We also discuss how these design motifs can imbue conjugated materials with appealing physical properties while simultaneously retaining or improving electronic capabilities.

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Section: Chalcogen Bondingmentioning

confidence: 99%

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Mullin

Sharber

Thomas

2021

Journal of Polymer Science

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“…46,47 Additionally, alkylthio side chains have also been effective in contributing to the conjugated polymer backbone with electron density. 48,49 Sulfur atom possesses some π-electron ability resulting from the formation of orbital overlapping of pπ(C)−dπ(S). 48,50 Furthermore, the empty 3d-orbital also endows sulfur-accepting electrons from other atoms, thus increasing intermolecular/intramolecular interaction through noncovalent bonding.…”

Section: ■ Introductionmentioning

confidence: 99%

“…48,50 Furthermore, the empty 3d-orbital also endows sulfur-accepting electrons from other atoms, thus increasing intermolecular/intramolecular interaction through noncovalent bonding. 49,51 Hence, alkylthio-substituted polymers certainly demonstrate suitable optoelectronic properties. Yang's group in 2019 reported the photovoltaic performance of polymers with an alkylthio side chain, exhibiting higher extinction coefficients and PCE of 13.16% with improved optoelectronic properties.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Additionally, alkylthio side chains have also been effective in contributing to the conjugated polymer backbone with electron density. , Sulfur atom possesses some π-electron ability resulting from the formation of orbital overlapping of pπ(C)–dπ(S). , Furthermore, the empty 3d-orbital also endows sulfur-accepting electrons from other atoms, thus increasing intermolecular/intramolecular interaction through noncovalent bonding. , Hence, alkylthio-substituted polymers certainly demonstrate suitable optoelectronic properties. Yang’s group in 2019 reported the photovoltaic performance of polymers with an alkylthio side chain, exhibiting higher extinction coefficients and PCE of 13.16% with improved optoelectronic properties .…”

Section: Introductionmentioning

confidence: 99%

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Benzobis(Thiazole)-Based Conjugated Polymer with Varying Alkylthio Side-Chain Positions for Efficient Fullerene-Free Organic Solar Cells

Raji

Wen

et al. 2021

ACS Appl. Mater. Interfaces

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Alkylthio groups can be used to modulate energy levels and molecular packing of organic semiconductors, which makes it important in the design of materials for organic solar cell. However, its effect has not been sufficiently exploited as most of the studies report introducing an alkylthio group to the donor unit and seldom to the acceptor unit of donor−acceptor conjugated polymers. In this report, two alkylthio-substituted polymers, namely, PBB-TSA and PBB-TSD, with benzo[1,2-d:4,5-d′]bis(thiazole) (BBT) as the acceptor unit and benzo[1,2-b:4,5-b′]dithiophene (BDT) as the donor unit, were rationally designed, synthesized, and applied in organic photovoltaics. An alkylthio side chain was substituted on the BBT-accepting unit for PBB-TSA, while for PBB-TSD, the alkylthio side chain was substituted on the BDT donor unit. PBB-TSA and PBB-TSD show upshifted and downshifted energy levels, respectively, compared to the nonsulfursubstituted material. Both polymers exhibit dominate face-on orientation, while PBB-TSD exhibits higher crystallinity compared to PBB-TSA. With the contribution of lower energy level and beneficial film morphology, the device based on PBB-TSD/IT-4F has much higher power conversion efficiency (PCE) of 14.6%, whereas the PBB-TSA blend had a lower PCE of 10.7%. 1,8-Diiodooctane can effectively optimize the blend film morphology, and the effect on device performance has also been demonstrated in detail. This result indicates that introducing an alkylthio side chain into the donor or acceptor moieties would result in materials with different energy levels and thus would be utilized to match with various acceptors, achieving optimized performance in organic solar cells.

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“…This relates in particular to the simple processability of this CPs that allow them to be obtained through electrochemical polymerization of monomeric systems, where the thickness and homogeneity can be controlled, and the CP can be directly obtained on the substrate, 11 thus facilitating their fabrication and reducing costs. This versatility depends mostly of its properties where include the ability to conduct electricity, optical properties, flexibility, low cost, and ease of fabrication, among others 12–14 …”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a new benzobisoxazole/thiophene derivative polymer and the effect of the substituent on the push/pull properties

Ahumada

Soto

Alemán

et al. 2021

Journal of Polymer Science

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Conducting polymer synthesis of a new benzobisoxazole/thiophene derivative is reported. The conjugated co‐polymer presents the lowest bandgap (1.78 eV) reported for a neutral benzobisoxazole/thiophene polymer. Electrochemical polymerization is carried out by cyclic voltammetry, and the new conducting polymer is characterized by Raman spectroscopy and X‐ray photoelectron spectroscopy. The results indicate that the coupling of the monomer unit occurs at the 2,2′ positions of the thiophene ring. Theoretical studies in derivatives of this family of compounds are conducted to validate the effect on the bandgap modulation due to the change in the substituent on the phenyl moiety of the monomer. The comparison between experimental and theoretical properties shows the substituents impact on the optical properties of the system, and its viability to be used in sensors.

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The effect of alkylthio substituents on the photovoltaic properties of conjugated polymers

Cited by 7 publications

References 49 publications

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Benzobis(Thiazole)-Based Conjugated Polymer with Varying Alkylthio Side-Chain Positions for Efficient Fullerene-Free Organic Solar Cells

Synthesis and characterization of a new benzobisoxazole/thiophene derivative polymer and the effect of the substituent on the push/pull properties

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