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Diketopyrrolopyrrole
JOURNAL OF POLYMER SCIENCE PART B-POLYMER PHYSICS · 2018 ·Vol. 56 ·期 11 ·833-841 · IF 2.499

Diketopyrrolopyrrole-based polymer nanowires: Control of chain conformation and nucleation

Xinxiu Cao,Liang Chen,Kefeng Zhao,Jiangang Liu,Yanchun Han

Understanding the nucleation process is very important in growing polymer nanowires as it plays a decisive role in determining the crystal structure and size distribution. Polymer chain conformation determines whether the polymer chains could assemble to nuclei or not. Here, chain conformation and the nucleation process were controlled to grow 3,6-bis-(thiophen-2-yl)- N , N ′-bis(2-decyl-1-tetradecyl)-1,4-dioxo-pyrrolo[3,4-c]pyrrole and thieno[3,2-b]thiophene (DT-PDBT-TT) nanowires. We changed the conformation of DT-PDBT-TT in solution and controlled the nucleation process by using a main solvent:cosolvent system. The main solvent was a low boiling point good solvent, and the cosolvent was consisted of two high boiling point solvents with different solubility. In fact, the chain conformation in the pristine solution was changed by choosing different main solvents (with H-bond, π–π or none interaction with the main chain) and temperatures. The absorption spectrum and TEM images showed that trichloro ethylene (TCE) was the best main solvent because it has H-bond interaction with the polymer main chain and DT-PDBT-TT conformation in it approaching unimer coil conformation, which is beneficial to grow nanowires. Mixed o-dichlorobenzene (ODCB) and anisole (AS) with different ratios were used to changing the solubility step by step to control nucleation process. Only when marginal cosolvent (ODCB:AS = 1:1) was added, could it decrease the nuclei number and avoided the aggregates simultaneously. As the main solvent evaporated slowly, the nucleation and growth happened, leading to the nanowires formation. The resulting nanowires were about 63 nm in width and one to two microns in length. The width of the DT-PDBT-TT structures suggests that the polymer chains are oriented along the fibril axis. Our results indicated that there are two requirements for the nanowire formation, (1) the polymer chain conformation should approach unimer coil; (2) the nucleation density should be optimized, not too much and no aggregation happened. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2018 , 56 , 833–841

研究领域: 高分子物理 · 材料科学 · 纳米科技 · 凝聚态物理 · 有机电子学
✓ 已验证 DOI 高影响因子
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Journal of Materials Chemistry B · 2024 ·Vol. 12 ·期 9 ·2294-2303 · IF 6.1

Design of donor–acceptor conjugated polymers based on diketopyrrolopyrrole for NIR-II multifunctional imaging

Mengyu Cao,Xuezhen Ma,Chang Wang,Wentao Zou,Fang Wang,Bing Yu,Hailin Cong,Youqing Shen

Diketopyrrolopyrrole (DPP) is an excellent photosensitizer and photothermal agent with the advantages of good planarity, strong electron affinity, high electron mobility, easy purification, easy structural modification and high molar absorption coefficient. It is regarded as one of the ideal choices for the design and synthesis of efficient organic photovoltaic materials. Therefore, two kinds of donor–acceptor (D–A) conjugated polymers were designed and synthesized with DPP as the acceptor, and their optical properties and applications in the near-infrared region were studied. The quantum yield (QY) of PBDT-DPP is 0.46%, and the highest temperature reached within 10 minutes after irradiation with a 660 nm laser is 60 °C. Another polymer, EDOT-DPP, has a QY of 0.48%, and its semiconductor polymer nanoparticle aqueous solution can reach 60 °C within 12 minutes under laser irradiation, achieving photothermal treatment of nude mice tumors. Both polymer NPs have good biocompatibility and promising applications in bioimaging and photothermal therapy.

CAS / MDL: 9004-74-4 2258654-78-1
研究领域: 材料科学 · 生物医学工程 · 光学成像
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Nanoscale · 2025 · IF 5.1

Organic electrochemical transistors based on a conjugated diketopyrrolopyrrole-dialkoxybithiazole copolymer

Zilan Chen,Xiaowei Zhao,Chengdong Wang,Wenxin Fang,Gang Ye,Lichuan Chen,Junyu Li,Yanxi Zhang

Organic electrochemical transistors (OECTs) are promising for bioelectronics due to their ability to amplify signals by converting ionic signals into electronic signals. The performance of OECTs relies heavily on the interaction between electrolyte ions and organic mixed ionic-electronic conductors (OMIECs). We examined how different aqueous electrolytes affect OECTs based on an ethylene glycol-substituted diketopyrrolopyrrole-dialkoxybithiazole copolymer (PDPP-TEG-2Tz), which is primarily p-type and electrochemically doped with anions. Our findings show that compared to the small, highly hydrated chloride anion (Cl−), the larger hexafluorophosphate (PF6−) and bis(trifluoromethanesulfonyl)imide (TFSI−) anions result in a lower threshold voltage and a faster transient response. Cations like Li+, Na+, and K+ have little impact on OECT performance. Additionally, we created a complementary inverter using p-type PDPP-TEG-2Tz with an n-type naphthalene diimide-bithiophene copolymer (PNDI2C8TEG-2T), achieving a maximum voltage gain of 22.6 at a supply voltage of 0.7 V.

CAS / MDL: 90076-65-6
研究领域: 材料科学 · 生物医学工程 · 电子器件
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ORGANIC ELECTRONICS · 2014 · IF 3.676

New diketopyrrolopyrrole-based organic dyes for highly efficient dye-sensitized solar cells

Sun-Sun Li,Ke-Jian Jiang,Fang Zhang,Jin-Hua Huang,Shao-Gang Li,Ming-Gong Chen,Lian-Ming Yang,Yan-Lin Song

Three diketopyrrolopyrrole (DPP) dyes ( ICD-3 , ICD-4 and ICD-5 ) with a D-π-A conjugation were designed and synthesized, where a symmetric phenyl-DPP-phenyl unit was used to connect a substituted diphenylamine and a thienyl acrylic acid, and two n -hexyl or 2-ethyl-hexyl chains were introduced on the periphery of the DPP macrocycle. The dyes were characterized by photophysical, electrochemical, and density functional theory calculations. Among the three dyes, the ICD-5 -based DSC afforded the best photovoltaic performance: a short circuit photocurrent density ( J sc ) of 16.34   mA/cm 2 , an open circuit voltage ( V oc ) of 753   mV, and a fill factor ( FF ) of 0.74, corresponding to an overall conversion efficiency ( η ) of 9.10% using I − / I 3 − redox couple-based liquid electrolyte under AM 1.5 conditions. The experimental results demonstrate that the DPP-based sensitizer is a promising option for DSCs, and rational molecular engineering is crucial for constructing highly efficient charge transfer sensitizers.

研究领域: 材料科学 · 能源技术
✓ 已验证 DOI 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2014 · IF 3.84

Colorimetric and On–Off fluorescent chemosensor for fluoride ion based on diketopyrrolopyrrole

Xiaofeng Yang,Luyi Zheng,Lijun Xie,Zheng Liu,Yexin Li,Rui Ning,Gege Zhang,Xiaoqian Gong,Bin Gao,Chunxiang Liu,Yu Cui,Guoxin Sun,Guangyou Zhang

Four colorimetric and On–Off fluorescence sensors based on diketopyrrolopyrrole (DPP) were synthesized for detection of fluoride anion. The anion binding studies indicated that sensors 1 – 4 showed remarkable selectivity and specificity toward F − ion over other anions. When binding with F − , the sensors of thiourea derivatives 1 and 2 showed a bathochromic shift of 78   nm in UV–vis spectra, and the urea derivatives 3 and 4 showed a bathochromic shift of 118   nm. Addition of F − ion to sensors 1 – 4 resulted in obvious quenching of fluorescence. The experimental results revealed that the formation of anionic species from the deprotonation of thiourea or urea moiety by the fluoride ion was responsible for the spectral changes. Calculations of the transition energies also verified such process. The spectral responses of sensors could be switched back and forth alternatively by adding F − and HSO 4 − anions into the DMSO solution, which indicated that sensors 1 – 4 were stable and could be used in reversible manner.

研究领域: 分析化学 · 超分子化学 · 传感器与仪器 · 荧光光谱学
✓ 已验证 DOI 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2015 · IF 4.097

A diketopyrrolopyrrole-based near-infrared sensor for selective recognition of fluoride ions

Xiaofeng Yang,Lijun Xie,Rui Ning,Xiaoqian Gong,Zheng Liu,Yexin Li,Luyi Zheng,Gege Zhang,Bin Gao,Yu Cui,Guoxin Sun,Guangyou Zhang

A new colorimetric and on–off fluorescence sensor based on diketopyrrolopyrrole (DPP) was synthesized for detection of fluoride anion. The sensor displayed a rapid responsivity and high selectivity and sensitivity toward F − over other anions, with a significant 267   nm bathochromic shift of the absorption maximum, and the new peak was located in the near-infrared region. Meanwhile, it could be easily observed that the sensor for F − ion changed from red to dark green by the naked eye, and from fluorescence red to non-fluorescence dark under UV lamp immediately after the F − ion was added. The experimental results revealed that the formation of anionic species from deprotonation of the hydrazone N–H moiety by fluoride ion was responsible for the spectral changes. Density function theory calculations were conducted to rationalize the optical response of the sensor. To the best of our knowledge, it was the first sensor for fluoride ever reported with a 267   nm red shift response, which could give a colorimetric and on–off fluorescence response instantly.

CAS / MDL: 4930-98-7 1112-67-0
研究领域: 化学传感器 · 材料科学
✓ 已验证 产品关联 DOI 高影响因子
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2018 · IF 2.88

Colorimetric chemosensors based on diketopyrrolopyrrole for selective and reversible recognition of fluoride ions

Yan Zhang,Xiaofeng Yang,Guoxin Sun,Hao Zhang,Xiaolei Liu,Fengqiao Zhu,Shuchun Qin,Ziqi Zhao,Yu Cui

A series of colorimetric and reversible receptors for fluoride anions based on diketopyrrolopyrrole (DPP) were designed and synthesized successfully. The position of nitro substituent on the phenylhydrazide affected the alteration of photophysical properties to varying degrees. While the photoluminescence intensity of receptor 1 was weaker than that of receptor 2 and receptor 3 on account of the formation of intramolecular hydrogen bond deriving from oxygen atom of nitro substituent and hydrogen atom of hydrazide . The receptor 2 was a preferable chemosensor for responding fluoride anions. The fluorescence was quenched in the presence of fluoride anion resulted from the photo-induced electron transfer (PET) effect from the amide. The formation of deprotonation species, which produced by hydrazide N H moiety and F − was answerable for the spectral changes. Especially, the spectral and color responses of receptors could be switched back and forth successively by adding F − and HSO 4 − anions in DMSO solution. These receptors could response fluoride anion sensitively, visually and selectively in a manner of reversible with a low determination.

研究领域: 化学 · 材料科学
✓ 已验证 DOI PubMed 高影响因子
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SYNTHETIC METALS · 2013 · IF 2.109

Effect of end-groups on the photovoltaic property of diphenyl substituted diketopyrrolopyrrole derivatives

Hangqi Shi,Zhuowei Gu,Xiao Gu,Hongbin Pan,Junying Pan,Xiaolian Hu,Congcheng Fan,Minmin Shi,Hongzheng Chen

In this work, a diphenyl substituted diketopyrrolopyrrole (DPP) and its two derivatives end-capped with fluorine and n -butyl respectively, namely PDPPP, FPDPPPF, and RPDPPPR, are designed and synthesized. The resulting molecules exhibit similar energy structures, i.e. both relatively narrow optical band gaps (1.75–1.79   eV) and deep highest occupied molecular orbital (HOMO) energy levels (−5.18 to −5.25   eV), implying that all of them are potentially good electron donors for organic solar cells (OSCs). However, three molecules show different photovoltaic performances when they are blended with [6,6]-phenyl-C 61 -butyric acid methyl ester (PC 61 BM) to fabricate OSCs: the RPDPPPR-based device gives the highest power conversion efficiency (PCE) of 1.59%, whereas the PCEs of PDPPP and FPDPPPF-based OSCs are 0.46% and 0.55%, respectively. Through atomic force microscopy (AFM), X-ray diffraction (XRD) and space charge limited current (SCLC) characterizations, the prominent role of end-groups in the photovoltaic properties of DPP derivatives is disclosed: terminal alkyl chains in RPDPPPR can promote molecular crystallization and lead to the formation of finer phase-separation domains in the blended film, which are in favor of charge generation and transportation in the photovoltaic devices. Thus, RPDPPPR provides the best photovoltaic property among three DPP molecules.

研究领域: 材料科学 · 有机电子学
✓ 已验证 产品关联 DOI 高影响因子
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ORGANIC ELECTRONICS · 2018 · IF 3.68

Synthesis and electrochromic properties of electrochromic polymers based on propylenedioxythiophene, diketopyrrolopyrrole and benzodithiophene units

Xiaoli Liu,Lingqian Kong,Hongmei Du,Yan Zhang,Jinsheng Zhao,Yu Xie

Two novel soluble polymers, PD-1 and PD-2, were synthesized based on three kinds of monomers , including propylenedioxythiophene (ProDOT), diketopyrrolopyrrole (DPP) and benzodithiophene (BDT), via Stille coupling reaction with the feed ratios (ProDOT:BDT:DPP) of 3:4:1, and 1:2:1, respectively. Wherein, propylenedioxythiophene (ProDOT) and benzodithiophene (BDT) exist as the donor unit, and diketopyrrolopyrrole (DPP) as the acceptor units. Both of the two copolymers were characterized via 1 H NMR, FT-IR spectra, X-ray photoelectron spectroscopy (XPS), cyclic voltammetry (CV), spectroelectrochemistry , switching kinetics, colorimetry and thermogravimetric analysis . Electrochemical studies demonstrate that both copolymers have the ability of rapid doping and dedoping and excellent stability. PD-1 displays a brown color in the neutral state, and a light green color in the oxidized state, while PD-2 exhibits gray green color in the neutral state and a transparent light green color in the oxidized state. As the content of the DPP remains constant, the changes in the content of the ProDOT unit can effectively control the color changes of the copolymers without apparent changes in bandgap ( E g ) values, and subsequently lead to the fine tune of the other properties of the copolymers, such as optical contrast, response time and coloring efficiency. The E g values of PD-1 and PD-2 are 1.55 eV and 1.52 eV, respectively. The optical contrasts are 42.36% (1600 nm) for PD-1 and 67.74% (at 1620 nm) for PD-2, both are ideal candidate materials for the fabrication of near infrared devices. They also have moderate optical contrast in the visible region, with fast response time and high coloring efficiency.

研究领域: 材料科学 · 电化学
✓ 已验证 产品关联 DOI 高影响因子
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

New Type Annihilator of π-Expanded Diketopyrrolopyrrole for Robust Photostable NIR-Excitable Triplet–Triplet Annihilation Upconversion

Fang Qi,Hong-Juan Feng,Yi Peng,Lin-Han Jiang,Le Zeng,Ling Huang

Near-infrared light excitable triplet–triplet annihilation upconversion (NIR TTA-UC) materials have attracted interest in a variety of emerging applications such as photoredox catalysis, optogenetics, and stereoscopic 3D printing. Currently, the practical application of NIR TTA-UC materials requires substantial improvement in photostability. Here, we found that the new annihilator of π-expanded diketopyrrolopyrrole (π-DPP) cannot activate oxygen to generate superoxide anion via photoinduced electron transfer, and its electron-deficient characteristics prevent the singlet oxygen-mediated [2 + 2] cycloaddition reaction; thus, π-DPP exhibited superior resistance to photobleaching. In conjunction with the NIR photosensitizer PdTNP, the upconversion efficiency of π-DPP is as high as 8.9%, which is eight times of the previously reported PdPc/Furan-DPP. Importantly, after polystyrene film encapsulation, less than 10% photobleaching was observed for this PdTNP/π-DPP-based NIR TTA-UC material after four hours of intensive NIR light exposure. These findings provide a type of annihilator with extraordinary photostability, facilitating the development of NIR TTA-UC materials for practical photonics.

CAS / MDL: 18908-66-2
研究领域: 材料科学 · 光子学 · 光电
✓ 已验证 产品关联 DOI PubMed 高影响因子
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DYES AND PIGMENTS · 2017 · IF 3.473

A non-fullerene electron acceptor with a spirobifluorene core and four diketopyrrolopyrrole arms end capped by 4-fluorobenzene

Cuixia Yuan,Wenqing Liu,Minmin Shi,Shuixing Li,Yuzhou Wang,Huanle Chen,Chang-Zhi Li,Hongzheng Chen

In this paper, a non-fullerene electron acceptor , SF(DPPFB) 4 , which owns a spirobifluorene core and four diketopyrrolopyrrole (DPP) arms end capped by 4-fluorobenzene, is designed and synthesized for solution-processable organic solar cells (OSCs). SF(DPPFB) 4 shows similar absorption bands as those of its non-fluorinated parent compound, SF(DPPB) 4 . However, the terminal fluorine atoms reduce the energy levels of SF(DPPFB) 4 , especially, its lowest unoccupied molecular orbital level decreases by 0.04 eV than that of SF(DPPB) 4 , which enlarges the energy offset between the electron donor and acceptor, favorable for the dissociation of excitons in OSCs. Moreover, the fluorination improves the electron mobility of SF(DPPFB) 4 . Thus, the OSCs with poly(3-hexylthiophene) as the electron donor and SF(DPPFB) 4 as the electron acceptor can provide a maximum power conversion efficiency of 4.42%, with a lifted short-circuit current ( J sc ) of 8.48 mA cm −2 .

研究领域: 材料科学 · 能源科学
✓ 已验证 DOI 高影响因子
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Journal of Materials Chemistry A · 2013 ·Vol. 2 ·期 3 ·653-662 · IF 0

Synthesis and photovoltaic performance of low band gap copolymers based on diketopyrrolopyrrole and tetrathienoacene with different conjugated bridges

Zhi Zeng,Ying Li,Jufu Deng,Qin Huang,Qiang Peng

Using tetrathienoacene (TT) and diketopyrrolopyrrole (DPP) units as donor and acceptor blocks, three new low band gap (LBG) conjugated copolymers (PTTDPO, PTTDPS and PTTDPSe) with different heterocycle bridges (furan, thiophene and selenophene) were designed and synthesized by Stille coupling polymerization reactions. Their structures were verified by 1HNMR spectroscopy and elemental analysis. All these copolymers exhibit broad absorption bands with small band gaps. UV-vis absorption spectra and cyclic voltammetry (CV) measurements indicated that the selenophene inclusion resulted in a reduction in the band gap, which could be attributed to a reduction of oxidation potentials and an increase of the electron affinities of the related copolymer. The density functional theory (DFT) calculations showed that PTTDPSe with selenophene bridges favoured a much more planar conformation than PTTDPO and PTTDPS, which afforded a higher hole mobility of 7.9 × 10−4 cm2 V−1 s−1. Photovoltaic properties of the copolymers blended with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an electron acceptor were investigated. The polymer solar cell (PSC) based on the structure of ITO/PEDOT:PSS/PTTDPSe:PC71BM (1 : 1.5, w/w)/Ca/Al exhibited a high power conversion efficiency (PCE) of 5.68% with an improved short circuit current density (Jsc) of 15.62 mA cm−2. The primary results show that changing heterocycle bridges with different electron-donating ability can easily and finely tune the optical absorptions, band gaps and energy levels of DPP-containing copolymers. The results also demonstrate that the TT unit is a new and promising electron-donating donor block for constructing highly efficient LBG photovoltaic materials.

研究领域: 高分子化学 · 材料科学 · 光伏器件 · 有机电子学 · 能源材料
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