n-Type conjugated polymers featuring low-lying lowest unoccupied molecular orbital (LUMO) energy levels are essential for achieving high-performance n-type organic thin-film transistors (OTFTs) and organic thermoelectrics (OTEs). However, the synthesis of acceptors with strong electron-withdrawing characteristics presents a significant challenge. Herein, a peripheral functionalization strategy is employed on the tricyclic framework anthracene by introducing dual N,O-bidentate BF/B(CN) groups to enhance its electron-withdrawing capability. This approach successfully navigates synthetic challenges, leading to the development of two novel acceptor building blocks: DBNF and DBNCN. Compared to the counterparts with a single N,O-bidentate BF/B(CN) moiety, DBNF and DBNCN exhibit an extended π-backbone, enhanced molecular packing, and improved electron-withdrawing properties. Utilizing these innovative acceptor monomers, copolymers, PDBNF and PDBNCN, are synthesized, which exhibit considerably suppressed LUMO ≈-4.0 eV. The deep LUMO of PDBNF together with its favourable bimodal packing orientation leads to remarkable electron mobility of 3.04 cm V s with improved stability in OTFTs. Importantly, efficient n-doping in OTEs is achieved with PDBNCN, exhibiting exceptional conductivity of 95.5 S cm and a maximum power factor of 147.8 μW m K-among the highest reported for solution-processed n-type polymers. This work underscores the effectiveness of introducing dual B←N and cyano functionalities in attaining high-performance n-type plastic electronics.
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http://dx.doi.org/10.1002/anie.202416669 | DOI Listing |
Phytochemistry
January 2025
Institute of Clinical Medical Sciences & Department of Pharmacy, China-Japan Friendship Hospital, Beijing, 100029, China. Electronic address:
Daphnane diterpenoids, as one of the representative types of diterpenoid compounds with rich structural diversity and significant biological activities, have an uncommon 5/7/6 tricyclic skeleton mainly found in species of Thymelaeaceae and Euphorbiaceae families. Due to the unique peculiarity of the framework and remarkable pharmacological activities, over the past three decades, novel structures have been continuously discovered and more structural subtypes have been derived. However, there is always a lack of a unified and convincing structural classification strategy for the summary of daphnane diterpenoids, which affects the in-depth and systematic research of pharmaceutical chemists and pharmacologists.
View Article and Find Full Text PDFOrg Lett
January 2025
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
A bioinspired alkylation dearomatization reaction was developed to construct the 5/6/6 fused-spiro tricyclic core framework and spiro-quaternary carbon chiral center. The usage of this approach for assembling these natural products of spirocyclic polycyclic polyprenylated acylphloroglucinols with an octahydrospiro-[cyclohexan-1,5'-indene] core is demonstrated by the first asymmetric total synthesis of highly oxidized hyperbeanol A.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
School of Chemistry and Environment, Yunnan Minzu University, Kunming 650500, P. R. China.
Total synthesis of (±)-applanatumol Y was achieved in 5 steps, featuring a cascade annulation including Michael addition, aldol condensation, and oxy-Michael addition reactions, all promoted by DBU. This approach offers a streamlined and cost-effective route for constructing complex tricyclic frameworks under mild and metal-free conditions.
View Article and Find Full Text PDFOrg Lett
December 2024
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences & Research Unit of Peptide Science, Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University, Lanzhou 730000, China.
To advance more efficient dearomatization approaches, we present herein an organocatalyzed asymmetric double dearomatization reaction of tricyclic phenols and alkoxybenzenes by leveraging a novel steric hindrance-regulated dearomatization strategy for nonfunctionalized phenols. This protocol allows the efficient synthesis of structurally complex polycyclic diketones with four tertiary carbon centers under mild conditions while also showcasing the potential of multiple dearomatizations for building intricate molecular frameworks from simple starting materials.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
A novel strategy for the synthesis of an advanced intermediate to the tigliane derivative euphordraculoate B was described, which led to the successful construction of the 5/5/6 tricyclic core framework as well as the multiple consecutive stereocenters on the skeleton. Key steps of the strategy include a chlorination reaction, an aldol reaction, and a Barbier-type allyl addition.
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