Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds

Feng, Dazeng; Barton, G. M.; Scott, Colleen N.

doi:10.1021/acs.orglett.9b00019

Cited by 16 publications

(16 citation statements)

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“…To obtain a more planar electron acceptor core, 3- and 6-position methyl-substituted DPP ( 3 ) was designed and synthesized via three-step reactions (Figure S1). Subsequently, compound 3 reacted with an electron-donating TPA and/or TPE unit that contains different rotors by Knoevenagel condensation to yield 2TPAVDPP, TPATPEVDPP and 2TPEVDPP, respectively (Figures A and S1). For comparison, the reported DPP-TPA was also synthesized (Figure S2).…”

Section: Results and Discussionmentioning

confidence: 99%

Acceptor Planarization and Donor Rotation: A Facile Strategy for Realizing Synergistic Cancer Phototherapy via Type I PDT and PTT

et al. 2022

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Tumor hypoxia seriously impairs the therapeutic outcomes of type II photodynamic therapy (PDT), which is highly dependent upon tissue oxygen concentration. Herein, a facile strategy of acceptor planarization and donor rotation is proposed to design type I photosensitizers (PSs) and photothermal reagents. Acceptor planarization can not only enforce intramolecular charge transfer to redshift NIR absorption but also transfer the type of PSs from type II to type I photochemical pathways. Donor rotation optimizes photothermal conversion efficiency (PCE). Accordingly, three 3,6-divinylsubstituted diketopyrrolopyrrole (DPP) derivatives, 2TPAVDPP, TPATPEVDPP, and 2TPEVDPP, with different number of rotors were prepared. Experimental results showed that three compounds were excellent type I PSs, and the corresponding 2TPEVDPP nanoparticles (NPs) with the most rotors possessed the highest PCE. The photophysical properties of 2TPEVDPP NPs are particularly suitable for in vivo NIR fluorescence imaging-guided synergistic PDT/PTT therapy. The proposed strategy is helpful for exploiting type I phototherapeutic reagents with high efficacy for synergistic PDT and PTT.

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Section: Results and Discussionmentioning

confidence: 99%

Acceptor Planarization and Donor Rotation: A Facile Strategy for Realizing Synergistic Cancer Phototherapy via Type I PDT and PTT

et al. 2022

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“…This π-stacking distance agrees well with thiophene flanking DPP polymers. 14,50 Although PDPPVTV shows some crystallinity, it did not show any π-stacking in its XRD patterns. The lists of 2θ and d-spacing values for both polymers are summarized in Table S2.…”

Section: Materials Synthesis and Characterizationmentioning

confidence: 95%

“…Compound 7 has been previously synthesized by our group, albeit with a different alkyl chain. 14 2.2. Synthesis of the PDPPVTT Polymer.…”

Section: Methodsmentioning

confidence: 99%

“…62 While we did not calculate the absorption coefficient of our polymers, the measured value of the monomer was previously reported and it is our expectation that the polymer would be very similar. 14 The absorption coefficient decreases sharply with increasing wavelength, which is reflected in the responsivity data as a function of wavelength. The R value decreases over 900 nm, which is limited by the band edge absorption due to the nature of the indirect band gap of the few-layered MoS 2 .…”

Section: Charge-carrier Mobility and Ofet Characteristicsmentioning

confidence: 99%

“…It is worth noting that in all of these cases, the DPP was flanked by an aryl group. Recently, our group reported the first example of a DPP core flanked with a vinyl group . To our knowledge, there are no reported vinylene-flanked DPP polymers to date.…”

Section: Introductionmentioning

confidence: 99%

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Vinyl-Flanked Diketopyrrolopyrrole Polymer/MoS₂ Hybrid for Donor–Acceptor Semiconductor Photodetection

Don

Das

et al. 2023

Chem. Mater.

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Polymers containing the 1,4-diketo-pyrrolo [3,4-c]pyrrole (diketopyrrolopyrrole, DPP) unit are highly desirable for optoelectronic devices. However, the requirements for the substituents flanking the DPP unit at the 3,6-positions are limited to aryl groups due to the lack of synthetic methods to prepare other substituted DPP. This paper describes the synthesis, characterization, and application of the first vinyl-flanked DPP polymers: DPP-vinylthiophene-vinyl (PDPPVTV) and DPP-vinyl-thiophene-thiophene (PDPPVTT). The position of the vinyl group is varied to determine its effect on the physical and optoelectrical properties of the polymers. The semicrystalline polymers record moderate molecular weights (M n ∼ 25−30 kDa), good solubility in chloroform, and high thermal stabilities (T d onset ∼ 400 °C). Both polymers have broad absorption bands in the solid state (abs λ max ∼ 800 nm) that extend into the nearinfrared (NIR) region (900−1000 nm). PDPPVTT has two orders of magnitude higher hole mobility than PDPPVTV (0.25 vs 0.0018 cm 2 V −1 s −1 ) and is used as a coating material in a MoS 2 FET device. The PDPPVTT/2D MoS 2 hybrid device shows higher photoresponsivity in the NIR region (10 3 A/W at 800 nm and 10 2 A/W at 1050 nm) than the pristine MoS 2 photodetector (10 2 A/ W at 800 nm and 0 A/W at 1050 nm).

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High‐Mobility Emissive n‐Type Polymer Semiconductors: Strong Synergy of Efficient Carrier‐Transporting Diketopyrrolopyrrole and Intense Light‐Emitting Phenylene‐Vinylene

Chen,

Wang,

Ren

et al. 2024

Adv Funct Materials

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High‐mobility emissive n‐type polymer semiconductors (HMEN‐CPs) are essential for organic optoelectronic devices. However, due to the lack of highly electron‐deficient building blocks with excellent physicochemical properties and the molecular design trade‐offs, the development of HMEN‐CPs has significantly lagged behind that of p‐type counterparts. Here, a new electron‐deficient acceptor, TFBVDPP is developed, by integrating the efficient carrier‐transporting diketopyrrolopyrrole and intense light‐emitting phenylene‐vinylene into a single molecule system. A series of all‐acceptor‐type polymers are synthesized by Pd‐catalyzed Suzuki polycondensation. The introduction of a vinyl bridge induces intra‐/intermolecular non‐covalent interactions, significantly narrowing the optical bandgap while enhancing coplanarity and crystallinity of the conjugated backbone, thus one of the polymers P1 exhibits ideal ambipolar transports with hole and electron mobilities reaching 4.6 and 3.7 cm2 V−1 s−1, respectively. Additionally, by directly homopolymerizing TFBVDPP, the non‐radiative transition is effectively suppressed, maintaining high electron transport while enhancing emission. This system shows excellent unipolar electron mobility (µe) and high quantum yield (Φ), achieving a record Φ · µe value exceeding 10−2 cm2 V−1 s−1, which is at least three orders of magnitude higher than the reported values. This study provides a new approach for developing HMEN‐CPs, and demonstrates their great potential in advancing organic optoelectronic technologies.

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Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds

Cited by 16 publications

References 50 publications

Acceptor Planarization and Donor Rotation: A Facile Strategy for Realizing Synergistic Cancer Phototherapy via Type I PDT and PTT

Acceptor Planarization and Donor Rotation: A Facile Strategy for Realizing Synergistic Cancer Phototherapy via Type I PDT and PTT

Vinyl-Flanked Diketopyrrolopyrrole Polymer/MoS₂ Hybrid for Donor–Acceptor Semiconductor Photodetection

High‐Mobility Emissive n‐Type Polymer Semiconductors: Strong Synergy of Efficient Carrier‐Transporting Diketopyrrolopyrrole and Intense Light‐Emitting Phenylene‐Vinylene

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Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds

Cited by 16 publications

References 50 publications

Acceptor Planarization and Donor Rotation: A Facile Strategy for Realizing Synergistic Cancer Phototherapy via Type I PDT and PTT

Acceptor Planarization and Donor Rotation: A Facile Strategy for Realizing Synergistic Cancer Phototherapy via Type I PDT and PTT

Vinyl-Flanked Diketopyrrolopyrrole Polymer/MoS2 Hybrid for Donor–Acceptor Semiconductor Photodetection

High‐Mobility Emissive n‐Type Polymer Semiconductors: Strong Synergy of Efficient Carrier‐Transporting Diketopyrrolopyrrole and Intense Light‐Emitting Phenylene‐Vinylene

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Vinyl-Flanked Diketopyrrolopyrrole Polymer/MoS₂ Hybrid for Donor–Acceptor Semiconductor Photodetection