Fluorination and chlorination effects on quinoxalineimides as an electron-deficient building block for n-channel organic semiconductors

Hasegawa, Tsukasa; Ashizawa, Minoru; Kawauchi, Susumu; Masunaga, Hiroyasu; Ohta, Nobuhiro; Matsumoto, Hidetoshi

doi:10.1039/c9ra02413a

Cited by 5 publications

(2 citation statements)

References 51 publications

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“…In short, according to the procedures previously reported, the intermediate diisopropyl dioxosuccinate ( 2 ) [ 22 ] was acquired by the oxidation of the tartaric acid esters with N ‐bromosuccinimide, and compound 4 [ 23 ] was obtained by the reduction of compound 3 . Then the diisopropyl 5,8‐dibromo‐6,7‐difluoroquinoxaline‐2,3‐dicarboxylate (compound 5 ) [ 24 ] was obtained via the condensation of compound 4 with compound 2. After that, the compound 6 was synthesized by transesterification reaction on the basis of compound 5 with p ‐toluenesulfonic acid as catalyst, and then, two thiophene units were installed onto the compound 6 to obtain compound 7 .…”

Section: Methodsmentioning

confidence: 99%

A New Ester‐Substituted Quinoxaline‐Based Narrow Bandgap Polymer Donor for Organic Solar Cells

Luo

Huang

et al. 2020

Macromol. Rapid Commun.

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The electron‐deficient ester group substitution in the sidechain of the commonly used electron‐withdrawing quinoxaline (Qx) unit is seldom studied, while ester‐substituted Qx units possess easy syntheses and facile modulation of the polymer solubility, and the enhanced electron‐withdrawing property of ester substituted Qx unit can theoretically broaden the optical absorption of the resulting polymers and improve the open circuit voltage in the corresponding organic solar cells (OSCs). In this work, a novel ester‐substituted Qx‐based narrow bandgap polymer (NBG) donor material PBDTT‐EFQx, which exhibits an absorption edge of 790 nm (bandgap < 1.6 eV), is designed and synthesized. Results show that the OSCs composed of PBDTT‐EFQx and PC71BM present the highest power conversion efficiency (PCE) of 6.8%, compared to PCEs of 5.0% for PBDTT‐EFQx:ITIC based devices and 4.1% for PBDTT‐EFQx:N2200 based devices, respectively. Characterizations and analyses indicate that the PC71BM‐based OSCs have well‐matched energy levels, better complementary light absorption, the highest and most balanced carrier mobilities, as well as the lowest degree of recombination losses, and therefore, leading to the highest PCE among the three types of OSCs. This work reveals that the ester‐substituted quinoxaline unit is one of the potential building blocks for NBG polymer donors.

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Section: Methodsmentioning

confidence: 99%

A New Ester‐Substituted Quinoxaline‐Based Narrow Bandgap Polymer Donor for Organic Solar Cells

Luo

Huang

et al. 2020

Macromol. Rapid Commun.

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“…1), fluorinated quinoxaline, thiadiazoloquinoxaline, and dithienobenzoquinoxaline, have been widely developed as high mobility semiconductors for OTFTs. 62,63 By proper modification of pyrazine-based acceptor units, the energy levels and charge carrier mobility can be easily tuned by the following methods: (i) changing the quinoxaline-based polymer backbone from acceptor-donor to acceptor-acceptor; (ii) introduction of different side chains to tune the solubility, aggregation behavior and intermolecular interactions of the molecule, which in turn affects the device performance of the polymer; (iii) introduction of functional groups onto the quinoxaline backbones, such as F atoms, Cl atoms, and cyano and ester groups, to lower the LUMO energy levels of the polymers. Therefore, it is highly desired to design other novel pyrazinebased acceptor units and investigate their structure-property relationship.…”

Section: Introductionmentioning

confidence: 99%

Dithiene-fused quinoxalineimide-based all-acceptor polymers for n-type organic semiconductors

Tu,

Wang,

et al. 2023

J. Mater. Chem. C

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Dipyridyl‐Fused Quinoxalineimide (DPQI): A Strong Electron‐Withdrawing Building Block for n‐Type Polymer Semiconductors

Li,

Yang,

Cheng

et al. 2024

Chemistry An Asian Journal

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Exploration of new electron‐withdrawing building blocks plays a key role in the development of n‐type organic semiconductors. Herein, a strong electron‐withdrawing building block, dipyridyl‐fused quinoxalineimide (DPQI), was successfully designed and synthesized. Single‐crystal structure reveals that DPQI molecule possesses a completely planar backbone, which is beneficial for charge transport. For comparison, dibenzo‐fused quinoxalineimide (DBQI) was also synthesized. The frontier molecular orbital (FMO) energy levels downshift with the incorporation of nitrogen atoms onto the p‐conjugated backbone of quinoxalineimide. Two acceptor‐acceptor (or all‐acceptor) polymers P(BTI‐DBQI) and P(BTI‐DPQI) based on DBQI and DPQI were synthesized, respectively. Two polymers exhibit deep lowest‐unoccupied molecular orbital (LUMO) levels (~‐3.5 eV). Additionally, P(BTI‐DPQI) exhibits unipolar n‐type charge transport with μe of 1.4×10‐4 cm2 V‐1 s‐1 in the organic field‐effect transistors (OFET), which render them highly attractive for developing n‐type semiconductors device. This work demonstrates that DPQI is a promising building block for constructing n‐type polymer semiconductors.

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Fluorination and chlorination effects on quinoxalineimides as an electron-deficient building block for n-channel organic semiconductors

Abstract: Three fluorinated or chlorinated quinoxalineimide units (QI-1F, QI-2F, and QI-2Cl) have been designed and developed.

Cited by 5 publications

References 51 publications

A New Ester‐Substituted Quinoxaline‐Based Narrow Bandgap Polymer Donor for Organic Solar Cells

A New Ester‐Substituted Quinoxaline‐Based Narrow Bandgap Polymer Donor for Organic Solar Cells

Dithiene-fused quinoxalineimide-based all-acceptor polymers for n-type organic semiconductors

Dipyridyl‐Fused Quinoxalineimide (DPQI): A Strong Electron‐Withdrawing Building Block for n‐Type Polymer Semiconductors

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