Solution-Processed Isoindigo- and Thienoisoindigo-Based Donor–Acceptor–Donor π-Conjugated Small Molecules: Synthesis, Morphology, Molecular Packing, and Field-Effect Transistor Characterization

Liao, Yu-Ting; Hsiao, Yi-Chun; Lo, Yuan‐Chih; Lin, Chang-Sheng; Lin, Po-Shen; Tung, Shih‐Huang; Wong, Ken‐Tsung

doi:10.1021/acsami.2c18049

Cited by 9 publications

(1 citation statement)

References 65 publications

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“…The clear charge separation leads to significant ICT interactions in the three regioisomers. Moreover, the slight overlap of the HOMO and LUMO on the central tribenzo[ a , c , i ]phenazine moiety may facilitate the ICT from the electron donor to the electron acceptor …”

Section: Resultsmentioning

confidence: 99%

Manipulating Intramolecular Charge Transfer and Supramolecular Interaction in D–A–D Conjugated Systems by Regioisomerization

Fang,

An,

Chen

et al. 2024

J. Org. Chem.

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Three new donor−acceptor−donor (D−A−D) architecture regioisomers comprising a large planar electron-withdrawing core tribenzo[a,c,i]phenazine and two identical electron-donating triphenylamines with different substitution patterns were designed and synthesized. Employing this regioisomerization strategy, the intramolecular charge-transfer interactions are effectively tuned and result in a significant bathochromic shift of photoluminescence maximum over 100 nm, which induces the corresponding emission band extending into the near-infrared region as well as giving a high solid-state quantum yield of 25%. Meanwhile, it is found that the supramolecular interactions of this series of regioisomers with planar electron-donor pyrene are greatly affected by the substitution pattern.

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Section: Resultsmentioning

confidence: 99%

Manipulating Intramolecular Charge Transfer and Supramolecular Interaction in D–A–D Conjugated Systems by Regioisomerization

Fang,

An,

Chen

et al. 2024

J. Org. Chem.

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Doped/Undoped A1‐A2 Typed Copolymers as ETLs for Highly Efficient Organic Solar Cells

Yang

Shen

Chen

et al. 2023

Adv Funct Materials

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The electron transport layer (ETL) is a critical component in achieving high device performance and stability in organic solar cells. Conjugated polyelectrolytes (CPEs) have become an attractive alternative due to film‐forming properties and ease of preparation. However, p‐type CPEs generally exhibit poor charge mobility and conductivity, incorporation of electron‐withdrawing units forming alternated D‐A conjugated backbone can make up for these deficiencies. Herein, the ratio of electron withdrawing moieties are further increased and two poly(A1‐alt‐A2) typed PIIDNDI‐Br and PDPPNDI‐Br based on the combination of naphthalene diimide (NDI) with isoindigo (IID) or diketopyrrolopyrrole (DPP) via direct arylation polycondensation are synthesized. These CPEs possess excellent alcohol solubility, a suitable lowest unocuppied molecular orbital energy level, and work function tunability. Surprisingly, the incorporation of IID and DPP units generate distinct self‐doping behaviors, which are confirmed by UV–vis absorption and ESR spectra. However, no matter doped or undoped, both CPEs present better charge‐transporting properties and conductivity when utilized as ETLs. The PIIDNDI‐Br and PDPPNDI‐Br display good universal compatibility with the blend of PM6:Y6 and PM6:L8‐BO, and PCEs of 18.32% and 18.36% are obtained, respectively, which also present excellent storage stability. In short, the combination of two different acceptors demonstrates an efficient strategy to design highly efficient ETLs for high performance photovoltaic devices.

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Unusual Cross‐Conjugation in Cyclic Dipeptide‐Based Building Blocks for Donor–Acceptor Semiconducting Conjugated Polymers

Wang,

Ye,

Wang

et al. 2024

Angewandte Chemie

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Cross conjugation, though prevalent in many organic compounds, is typically considered less effective for electron delocalization compared to linear conjugation. Consequently, it is rarely used as the backbone structure for semiconducting conjugated polymers. In this study, we designed and synthesized a novel building block, TIDP, which features a central cyclic dipeptide with cross conjugation characteristics. Strong intramolecular hydrogen bonding interactions confer TIDP with a highly rigid and coplanar conformation. Importantly, theoretical calculations reveal that π electrons are well delocalized across the entire structure, despite its low aromaticity. Conjugated polymers incorporating TIDP exhibit high charge carrier mobilities, demonstrating the effective π electron delocalization of this innovative building block. Our findings show that with rational design, cross conjugation can achieve effective π electron delocalization, providing a valuable approach for developing high‐performance conjugated polymers for organic electronic materials.

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Solution-Processed Isoindigo- and Thienoisoindigo-Based Donor–Acceptor–Donor π-Conjugated Small Molecules: Synthesis, Morphology, Molecular Packing, and Field-Effect Transistor Characterization

Cited by 9 publications

References 65 publications

Manipulating Intramolecular Charge Transfer and Supramolecular Interaction in D–A–D Conjugated Systems by Regioisomerization

Manipulating Intramolecular Charge Transfer and Supramolecular Interaction in D–A–D Conjugated Systems by Regioisomerization

Doped/Undoped A1‐A2 Typed Copolymers as ETLs for Highly Efficient Organic Solar Cells

Unusual Cross‐Conjugation in Cyclic Dipeptide‐Based Building Blocks for Donor–Acceptor Semiconducting Conjugated Polymers

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