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1044598-80-2Relevant academic research and scientific papers
Diketopyrrolopyrrole-based acceptor-acceptor conjugated polymers: The importance of comonomer on their charge transportation nature
Ge, Cong-Wu,Mei, Chong-Yu,Ling, Jun,Zhao, Fu-Gang,Li, Hong-Jiao,Liang, Long,Wang, Jin-Tu,Yu, Jin-Cheng,Shao, Wei,Xie, Yong-Shu,Li, Wei-Shi
, p. 2356 - 2366 (2014)
Besides the donor-acceptor (D-A) type, acceptor-acceptor (A-A) polymers are another class of important alternative conjugated copolymers, but have been less studied in the past. In this study, two kinds of A-A polymers, P1 and P2, have been designed and synthesized based on diketopyrrolopyrrole in combination with the second electron-deficient unit, perylenediimide or thieno[3,4-c] pyrrole-4,6-dione. UV-vis absorption spectroscopy revealed that these two kinds of polymers have a band gap of 1.28-1.33 eV. Their highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels are around -5.6 and -4.0 eV for P1 polymers, whereas -5.4 and -3.7 eV for P2 polymers, respectively. Density functional theory study disclosed that P1 backbone is in a vastly twisting state, whereas that of P2 is completely planar. Furthermore, organic field-effect transistor devices were fabricated using these two kinds of polymers as the active material. Of interest, the devices based on P1 polymers displayed n-channel behaviors with an electron mobility in the order of 10 -4 cm2 V-1 s-1. In contrast, the P2-based devices exhibited only p-channel charge transportation characteristics with a hole mobility in the order of 10-3 cm2 V -1 s-1.
Optical properties of oligothiophene substituted diketopyrrolopyrrole derivatives in the solid phase: Joint J- and H-type aggregation
Kirkus, Mindaugas,Wang, Linjun,Mothy, Sebastien,Beljonne, David,Cornil, Jerome,Janssen, Rene A. J.,Meskers, Stefan C. J.
, p. 7927 - 7936 (2012)
Photophysical properties of diketopyrrolopyrrole derivatives substituted with oligothiophenes are investigated. All compounds are found to be fluorescent both in solution and in the solid phase. At low temperature in the solid, fluorescence originates from excimer-like excited states. Comparison of absorption and fluorescence excitation spectra taken under matrix isolated conditions and on solid films show the presence of both J- and H-type absorption bands in the solid phase. Quantum-chemical calculations, including exciton-phonon coupling to account for deviations from the Born-Oppenheimer approximation, are performed to simulate the band shape of the lowest absorption band in the molecular solid. The joint presence of J- and H-bands is explained by the presence of two molecules in the unit cell. The Davydov splitting is substantial for molecules with linear alkyl substituents on the nitrogen atom (on the order of 0.2 eV) but can be reduced to almost zero by introducing branching at the β-carbon of the alkyl side chain.
Rapid release from near-infrared polymer loaded liposomes for photothermal and chemo-combined therapy
Li, Dehua,Zhang, Meiduo,Yao, Jingke,Zhang, Zhe
, p. 2274 - 2277 (2019/02/05)
PEGylated liposomal doxorubicin is a polymeric antitumor drug approved clinically by the Food and Drug Administration, but it has no essentially increasing efficacy compared to free doxorubicin (DOX) because of the slow release rate. In this paper, a near-infrared polymer was designed and encapsulated in liposomes to photothermally accelerate the release of DOX. This polymer loaded liposome provides a maximum absorption that covers the ideal phototherapeutic window between 800 and 850 nm, which ensures an efficient photothermal release of DOX as a nano drug for the delivery of photothermal and chemo-combined therapy in a highly efficient cancer treatment.
Two-acceptor one-donor random terpolymers comprising thiophene- and phenyl-capped diketopyrrolopyrrole for organic photovoltaics
Sambathkumar,Varathan,Subramanian,Somanathan
, p. 20113 - 20122 (2018/12/13)
A series of random terpolymers comprising two electron deficient phenyl (PDPP) and thiophene (ThDPP)-capped diketopyrrolopyrrole (DPP) in conjugation with the electron-donating thiophene moiety are synthesised using Stille coupling. Their optical properties, energy levels, hole mobility, crystallinity and solar cell device performance can be systematically fine-tuned by controlling the molar ratio between ThDPP/PDPP (30/70, 50/50, 70/30, and 90/10) contents in the polymer backbone. Herein, we find that the crystalline properties and hole mobility of the terpolymer are enhanced by increasing ThDPP content in the polymer backbone. However, increasing PDPP content leads to low hole mobility and weak crystalline features. These characteristic features afford remarkable effect on the solar cell device performance. Bulk heterojunction (BHJ) solar cells are constructed by using these random terpolymers as donor materials and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the acceptor. The best device performances are obtained for polymer P5T5P with the ThDPP/PDPP ratio of 50/50 and power conversion efficiency (PCE) of 2.9% due to balanced charge carrier mobility and optimized crystallinity in addition to good miscibility and favorable surface morphology with the fullerene acceptor. This study demonstrates that improved control of the crystallinity of the polymer donor through structural engineering can greatly help in improving device performance.
Importance of solubilizing group and backbone planarity in low band gap polymers for high performance ambipolar field-effect transistors
Lee, Joong Suk,Son, Seon Kyoung,Song, Sanghoon,Kim, Hyunjung,Lee, Dong Ryoul,Kim, Kyungkon,Ko, Min Jae,Choi, Dong Hoon,Kim, Bong Soo,Cho, Jeong Ho
, p. 1316 - 1323 (2012/08/28)
We investigated the performance of ambipolar field-effect transistors based on a series of alternating low band gap polymers of oligothiophene and diketopyrrolopyrrole (DPP). The polymers contain oligothiophene units of terthiophene [T3] and thiophenethienothiophene-thiophene [T2TT] and DPP units carrying branched alkyl chains of 2-hexyldecyl [HD] or 2-octyldodecyl [OD]. The structural variation allows us to do a systematic study on the relationship between the interchain stacking/ordering of semiconducting polymers and their resulting device performance. On the basis of synchrotron X-ray diffraction and atomic force microscopy measurements on polymer films, we found that longer branched alkyl side chains, i.e., OD, and longer and more planar oligothiophene, i.e., T2TT, generate the more crystalline structures. Upon thermal annealing, the crystallinity of the polymers was largely improved, and polymers containing a longer branched alkyl chain responded faster because longer alkyl chains have larger cohesive forces than shorter chains. For all the polymers, excellent ambipolar behavior was observed with a maximum hole and electron mobility of 2.2 and 0.2 cm2 V-1 ss, respectively.
Click -functionalization of [60]fullerene and graphene with an unsymmetrically functionalized diketopyrrolopyrrole (DPP) derivative
Castelain, Marta,Salavagione, Horacio,Segura, Jose L.
supporting information; experimental part, p. 2798 - 2801 (2012/08/14)
A synthetic strategy is developed that allows for the facile functionalization of carbon nanostructures thus providing the possibility of comparing the striking different optical and electrochemical properties of ensembles based on the diketopyrrolopyrrole (DPP) chromophore covalently attached to either [60]fullerene or graphene.
Synthesis of diketopyrrolopyrrole (DPP) derivatives comprising bithiophene moieties
Stas, Sara,Sergeyev, Sergey,Geerts, Yves
supporting information; experimental part, p. 1837 - 1845 (2010/04/06)
Herein we disclose an easily applicable method for the synthesis of diketopyrrolopyrrole (DPP) derivatives comprising bithiophene moieties, with different substituents on the nitrogen atoms (Me, n-octyl, 3,5-di-tert-butylbenzyl, Boc) and on the thiophene rings (C6H13, C12H25), in good yields and purities. A comparison is made between the previously described method from literature and our more efficient approach regarding number of steps, overall yields and ease of synthesis and purification.
DIKETOPYRROLOPYRROLE POLYMERS AS ORGANIC SEMICONDUCTORS
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Page/Page column 45-46, (2008/06/13)
The present invention relates to polymers comprising a repeating unit of the formula (l) and their use as organic semiconductor in organic devices, especially a diode, an organic field effect transistor and/or a solar cell, or a device containing a diode and/or an organic field effect transistor, and/or a solar cell. The polymers according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).
