An<i>N</i>-oxide containing conjugated semiconducting polymer with enhanced electron mobility<i>via</i>direct (hetero)arylation polymerization

He, Xiandong; Ye, Feng; Jun, Guo; Chang, Wenju; Ma, Bingxu; Ding, Riqing; Wang, Sijing; Liang, Yong; Hu, Dehua; Guo, Zihao; Ma, Yan

doi:10.1039/d3py00207a

Cited by 5 publications

(3 citation statements)

References 66 publications

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“…Unexpectedly, P3DPP-BT with three DPP blocks and one BT block in the repeating unit exhibits inferior transport characteristics with low electron/hole mobilities of 2 × 10 −2 /5 × 10 −2 cm 2 V −1 s −1 , respectively, causing a nearly 55 times decrease of electron mobilities compared with P2DPP-BT . Based on our previous research on ambipolar DPP-based polymers, 24 this work utilizes an acceptor modulation strategy to further improve the electron transport in the related DPP-polymers. As expected, the ambipolar charge transport behavior is observed in the three samples.…”

Section: Resultsmentioning

confidence: 99%

“…17 It is found that the A-A backbone architecture could be fairly effective to deepen the lowest unoccupied molecular orbital (LUMO) energy levels, strengthen intermolecular interactions, and increase electron mobilities (m e ). [18][19][20][21][22][23][24][25][26] For instance, Guo et al developed a bis-diketopyrrolopyrrole (2DPP) based polymer P2DPP-TT (Fig. 1a), which shows stronger electron deficiency and intermolecular interactions than its single-DPP counterpart.…”

Section: Introductionmentioning

confidence: 99%

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An acceptor-quantity modulation strategy for high-performance ambipolar semiconducting polymers: from a dual-acceptor to a quad-acceptor backbone

Jiao,

Zuo,

Shen

et al. 2024

J. Mater. Chem. C

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An acceptor-quantity modulation strategy for high-performance ambipolar semiconducting polymers: from a dual-acceptor to a quad-acceptor backbone

Jiao,

Zuo,

Shen

et al. 2024

J. Mater. Chem. C

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“…Pyridine-N-oxide has been shown to have similar properties as the tyrosine/tyrosyl radical redox couple and can thus serve as an electron shuttle in artificial photosynthesis (Figure 3D). 42,43 Along the same lines, polymeric N-oxides have been found to have special electron transport properties useful for the construction of semiconducting polymers 44 and interlayer materials for organic solar cells. 45 This special radical reactivity might also be the reason for the antioxidant properties, which have been suggested for several amphiphilic N-oxides used in cosmetic applications.…”

Section: Properties Of N-oxidesmentioning

confidence: 93%

Medicinal Chemistry of Drugs with N-Oxide Functionalities

Kobus,

Friedrich,

Zorn

et al. 2024

J. Med. Chem.

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Molecules with N-oxide functionalities are omnipresent in nature and play an important role in Medicinal Chemistry. They are synthetic or biosynthetic intermediates, prodrugs, drugs, or polymers for applications in drug development and surface engineering. Typically, the N-oxide group is critical for biomedical applications of these molecules. It may provide water solubility or decrease membrane permeability or immunogenicity. In other cases, the N-oxide has a special redox reactivity which is important for drug targeting and/or cytotoxicity. Many of the underlying mechanisms have only recently been discovered, and the number of applications of N-oxides in the healthcare field is rapidly growing. This Perspective article gives a short summary of the properties of N-oxides and their synthesis. It also provides a discussion of current applications of N-oxides in the biomedical field and explains the basic molecular mechanisms responsible for their biological activity. ■ SIGNIFICANCE Relevance of N-oxides for Medicinal Chemistry:• N + −O − bonds are highly polar and form strong hydrogen bonds. They may be inert or reactive in biological systems depending on their substituents.• N-Oxide groups can be used to increase the solubility of drugs and decrease membrane permeability.• Many heteroaromatic and aniline-derived N-oxides are reduced enzymatically in vivo and find applications as hypoxia-activated prodrugs.• Polymeric N-oxides have excellent blood compatibility, are nonimmunogenic and are nonadhesive for microorganisms (stealth materials).

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Rational Molecular Design of Diketopyrrolopyrrole‐Based n‐Type and Ambipolar Polymer Semiconductors

Shen,

Jiang,

Wang

et al. 2024

Chemistry A European J

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Diketopyrrolopyrrole (DPP)‐based polymer semiconductors have drawn great attention in the field of organic electronics due to the planar structure, decent solubilizing capability, and high crystallinity. However, the electron‐deficient capacity of DPP derivatives are not strong enough, leading to relatively high‐lying lowest unoccupied molecular orbital (LUMO) energy levels of the corresponding polymers. As a result, n‐type and ambipolar DPP‐based polymers are rare and their electron mobilities also lag far behind the p‐type counterparts, which limits the development of important p‐n‐junction‐based electronic devices. Therefore, new design strategies have been proposed recent years to develop n‐type/ambipolar DPP‐based polymers with improved performances. In this view, these molecular design strategies are summarized, including copolymerization of DPP with different acceptors and weak donors, DPP flanked aromatic ring modification, DPP‐core ring expansion and DPP dimerization. The relationship between the chemical structures and organic thin‐film transistor performances is intensively discussed. Finally, a perspective on future trends in the molecular design of DPP‐based n‐type/ambipolar polymers is also proposed.

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AnN-oxide containing conjugated semiconducting polymer with enhanced electron mobilityviadirect (hetero)arylation polymerization

Abstract: In this paper, an N-oxide building block, 4,4'-dimethyl-[2,2'-bithiazole] 3,3'-dioxide (MeBTzO), was designed and synthesized by oxidation of sp2- nitrogen in aromatic ring. Theoretical calculation results showed that MeBTzO has higher...

Cited by 5 publications

References 66 publications

An acceptor-quantity modulation strategy for high-performance ambipolar semiconducting polymers: from a dual-acceptor to a quad-acceptor backbone

An acceptor-quantity modulation strategy for high-performance ambipolar semiconducting polymers: from a dual-acceptor to a quad-acceptor backbone

Medicinal Chemistry of Drugs with N-Oxide Functionalities

Rational Molecular Design of Diketopyrrolopyrrole‐Based n‐Type and Ambipolar Polymer Semiconductors

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