Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties

Ding, Fangwei; Xia, Debin; Ge, Congwu; Ding, Xiaoyi; Deng, Ruibin; Yang, Yulin; Lin, Kaifeng; Gao, Xike

doi:10.1016/j.cclet.2022.02.040

Cited by 7 publications

(4 citation statements)

References 37 publications

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“…The strategy also involved attaching triisopropylsilyl groups to the anthracene core to balance solubility and charge carrier properties. The BSPQ derivative exhibited deeper frontier orbital energy levels and enhanced electron mobility compared to the BTPQ [55].…”

Section: Quinoxalines As N-type Transistor Materialsmentioning

confidence: 97%

Quinoxaline derivatives as attractive electron-transporting materials

Abid,

Ali,

Gulzar

et al. 2023

Beilstein J. Org. Chem.

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This review article provides a comprehensive overview of recent advancements in electron transport materials derived from quinoxaline, along with their applications in various electronic devices. We focus on their utilization in organic solar cells (OSCs), dye-sensitized solar cells (DSSCs), organic field-effect transistors (OFETs), organic-light emitting diodes (OLEDs) and other organic electronic technologies. Notably, the potential of quinoxaline derivatives as non-fullerene acceptors in OSCs, auxiliary acceptors and bridging materials in DSSCs, and n-type semiconductors in transistor devices is discussed in detail. Additionally, their significance as thermally activated delayed fluorescence emitters and chromophores for OLEDs, sensors and electrochromic devices is explored. The review emphasizes the remarkable characteristics and versatility of quinoxaline derivatives in electron transport applications. Furthermore, ongoing research efforts aimed at enhancing their performance and addressing key challenges in various applications are presented.

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Section: Quinoxalines As N-type Transistor Materialsmentioning

confidence: 97%

Quinoxaline derivatives as attractive electron-transporting materials

Abid,

Ali,

Gulzar

et al. 2023

Beilstein J. Org. Chem.

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“…Generally, the most successful molecular design strategy to broaden the absorption range is donor–acceptor (D–A) type containing electron donor and acceptor structures, [ 19 ] whose bandgap determined by the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) can be easily regulated by the variation of donor and acceptor units. [ 20 ] Compared with the single‐donor or single‐acceptor photothermal materials, the HOMO‐LUMO orbitals of the D–A typed materials are hybridized, the bandgaps are narrowed, and the absorption spectra are redshifted due to the intramolecular charge transfer (ICT) effect. [ 21 ] As a result, some D–A molecules are able to display absorption spectra extending into the near‐infrared region, which can be highly beneficial for photothermal conversion processes.…”

Section: Introductionmentioning

confidence: 99%

Manipulating Molecular Motion of [1,2,5]Thiadiazolo[3,4‐g]Quinoxaline‐6,7‐Dicarboxylate Small Molecules for Highly Efficient Solar‐Thermal Water Evaporation and Thermoelectric Power Generation

Wang,

et al. 2024

Adv Funct Materials

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Organic conjugated molecules are a category of high solar harvesting material that can convert energy into heat and be utilized as solar‐driven water‐electricity co‐generation. However, the limited absorption range and insufficient photothermal conversion efficiency hinder their application. Herein, two new organic molecules TPA‐BTQ and TPA‐SBTQ, featuring strong electron withdrawing [1,2,5]thiadiazolo[3,4‐g]quinoxaline‐6,7‐dicarboxylate (BTQ) center, terminated by triphenylamine or thiophene‐bridged triphenylamine are designed and synthesized. Detailed theory calculations and spectral analysis confirm that the BTQ unit induces strong intramolecular charge transfer and expands the absorption across a wide spectra range. The flexible alky chain substituted on thiophene inhibits the over‐aggregation and affords more rotation space, leading to suppressed radiative transition and efficient solar‐thermal conversion. Therefore, TPA‐SBTQ powder shows broad absorption across 350 to 1300 nm with a high photothermal conversion efficiency of 18.28% under 1 kW m−2 simulated solar irradiation. Moreover, TPA‐SBTQ is further explored for solar‐thermal conversion applications. The evaporation rate of TPA‐SBTQ solar‐driven water evaporator can reach a remarkable 1.337 kg m−2 h−1 with 92% of water evaporation efficiency under 1 kW m−2 solar irradiation. This study provides guidance for the rational design of high‐efficient organic solar‐thermal materials with a wide absorption spectrum and excellent photothermal conversion efficiency at the molecular level for emerging photothermal‐related applications.

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“…Benzo[ b ]thiophene-2,3-dione, also known as thioisatin, is a type of five-membered-ring compound with a 2,3-dicarbonyl structure. 1 As compared to the wide application of isatins for the construction of N-containing heterocycles, 2,3 thioisatins, as potential building blocks of sulfur-containing heterocycles, have not received as much attention from chemists.…”

Section: Introductionmentioning

confidence: 99%