A Convenient Synthesis of Dithieno[3,2-b:2′,3′-d]thiophenes from Thiophene

Park, Kyung Hyun; Park, Joon Bum; Zong, Kyukwan

doi:10.1055/s-0035-1562531

Cited by 10 publications

(1 citation statement)

References 6 publications

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“…51 Meanwhile, as shown in Figure 7b, OFETs with PEDOT:PSS exhibited a linear relationship between drain current (I DS ) and drain voltages (V DS ) at low V DS due to efficient hole injection, indicating a low contact resistance between the electrodes and the semiconductors. To confirm the broad applicability of PEs in OFETs, we applied our method to two other high-performance organic semiconductors, including the p-type dithieno[3,2-b:20,30-d]thiophene derivatives (DTT-8) 52,53 and the n-type furan-thiophene quinoidal compound (TFT-CN) 54 (Figures S19−S22 and 24). The HOMO and LUMO energy levels of the three organic semiconductors, as presented in Table S4, exhibit partial alignment with the work function of PE-T (4.7 eV, Figure S25).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Stepwise Aggregation Control of PEDOT:PSS Enabled High-Conductivity, High-Resolution Printing of Polymer Electrodes for Transparent Organic Phototransistors

Xiao,

Shen,

Tie

et al. 2024

ACS Appl. Mater. Interfaces

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Electrohydrodynamic (EHD) jet printing is a widely employed technology to create high-resolution patterns and thus has enormous potential for circuit production. However, achieving both high conductivity and high resolution in printed polymer electrodes is a challenging task. Here, by modulating the aggregation state of the conducting polymer in the solution and solid phases, a stable and continuous jetting of PEDOT:PSS is realized, and high-conductivity electrode arrays are prepared. The line width reaches less than 5 μm with a record-high conductivity of 1250 S/cm. Organic field-effect transistors (OFETs) are further developed by combining printed source/drain electrodes with ultrathin organic semiconductor crystals. These OFETs show great light sensitivity, with a specific detectivity (D*) value of 2.86 × 1014 Jones. In addition, a proof-of-concept fully transparent phototransistor is demonstrated, which opens up new pathways to multidimensional optical imaging.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Stepwise Aggregation Control of PEDOT:PSS Enabled High-Conductivity, High-Resolution Printing of Polymer Electrodes for Transparent Organic Phototransistors

Xiao,

Shen,

Tie

et al. 2024

ACS Appl. Mater. Interfaces

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Facile Synthesis of Dithienobenzothiadiazoles and D18−Cl Polymer via Na₂S‐Mediated Rapid Thiophene‐Annulations for Organic Solar Cells

Kang,

Kim,

Zong

2024

ChemSusChem

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A new synthetic route for rapidly constructing dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2‐c][1,2,5]thiadiazoles via a Na2S promoted thiophene‐annulation was developed and successfully applied to cost‐effective synthesis of D18‐Cl polymer that has attracted a great attention as a highly efficient polymer donor in the field of bulk‐heterojunction polymer solar cells. A commercially available 4,7‐dihalo‐5,6‐difluorobenzo[c][1,2,5]thiadiazole was converted into a range of the corresponding 4,7‐dialkynlated compounds under Sonogashira reaction condition. Subsequently, Na2S promoted thiophene‐annulations on them furnished DTBT and its derivatives in excellent yields within 10 min. With DTBT in hands, D18‐Cl was concisely synthesized via two distinct routes respectively, which are greatly benefited from less synthetic steps, mild reaction condition, less synthetic complexity, and high overall yields. The developed protocol provides a straightforward and reliable synthetic tool, which is highly conducive in cutting the synthetic cost and complexity for production of DTBT based organic electronic materials and therefore moving forward the potential commercialization of organic solar cells.

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Efficient Synthesis of Dithieno[3,2‐B:2’,3’‐d]Thiophenes Derivatives with Promising Optoelectronic Properties Via a One‐Pot, Two‐Step Method with Elemental Sulfur

Zhang,

Li,

et al. 2024

ChemistrySelect

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Dithieno[3,2‐b:2’,3’‐d]thiophene (DTT) derivative contains three annulated thiophene rings, which have attracted great attention in the field of materials due to its planar and conjugated molecular, structural rigidity, and increased solubility. Herein, the one‐step modular construction of a series of structurally well‐defined 2,6‐disubstituted dithieno[3,2‐b:2’,3’‐d]thiophenes (2,6‐DTT) involves Pd/Cu(I)‐catalyzed Sonogashira coupling and LiNH2‐mediated ring‐closing reaction with element sulfur was reported. The method allows the selective and straightforward introduction of different aryl substitution into DTT without otherwise tedious separation and purification processes. The preliminary study of the thermal and photophysical properties demonstrated that the introduction of substituent in phenyl has great impact for the parent molecule, which enable this protocol to synthesis high‐performance 2,6‐DTT through the different alkynes.

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A Convenient Synthesis of Dithieno[3,2-b:2′,3′-d]thiophenes from Thiophene

Cited by 10 publications

References 6 publications

Stepwise Aggregation Control of PEDOT:PSS Enabled High-Conductivity, High-Resolution Printing of Polymer Electrodes for Transparent Organic Phototransistors

Stepwise Aggregation Control of PEDOT:PSS Enabled High-Conductivity, High-Resolution Printing of Polymer Electrodes for Transparent Organic Phototransistors

Facile Synthesis of Dithienobenzothiadiazoles and D18−Cl Polymer via Na₂S‐Mediated Rapid Thiophene‐Annulations for Organic Solar Cells

Efficient Synthesis of Dithieno[3,2‐B:2’,3’‐d]Thiophenes Derivatives with Promising Optoelectronic Properties Via a One‐Pot, Two‐Step Method with Elemental Sulfur

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A Convenient Synthesis of Dithieno[3,2-b:2′,3′-d]thiophenes from Thiophene

Cited by 10 publications

References 6 publications

Stepwise Aggregation Control of PEDOT:PSS Enabled High-Conductivity, High-Resolution Printing of Polymer Electrodes for Transparent Organic Phototransistors

Stepwise Aggregation Control of PEDOT:PSS Enabled High-Conductivity, High-Resolution Printing of Polymer Electrodes for Transparent Organic Phototransistors

Facile Synthesis of Dithienobenzothiadiazoles and D18−Cl Polymer via Na2S‐Mediated Rapid Thiophene‐Annulations for Organic Solar Cells

Efficient Synthesis of Dithieno[3,2‐B:2’,3’‐d]Thiophenes Derivatives with Promising Optoelectronic Properties Via a One‐Pot, Two‐Step Method with Elemental Sulfur

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Facile Synthesis of Dithienobenzothiadiazoles and D18−Cl Polymer via Na₂S‐Mediated Rapid Thiophene‐Annulations for Organic Solar Cells