84632-54-2Relevant academic research and scientific papers
The synthesis and highly sensitive detection of water content in THF using a novel solvatochromic AIE polymer containing diketopyrrolopyrrole and triphenylamine
Wang, Lingyun,Yang, Lingling,Li, Lin,Cao, Derong
, p. 6706 - 6713 (2016)
A novel electron donor-acceptor polymer (N1) containing diketopyrrolopyrrole as an electron acceptor and triphenylamine as an electron donor has been designed and synthesized. N1 is shown to possess the remarkable dual properties of solvatochromism and aggregation-induced emission (AIE). Importantly, N1 is found to serve as a fluorescence indicator for the qualitative and quantitative detection of low-level water in THF. Moreover, the quaternization of N1 by CH3I gave ammonium-salt P1. A selective fluorescence turn-on probe for bovine serum albumin (BSA) detection and quantification is developed by taking advantage of the aggregating process of P1. It is found that the intrinsic weak fluorescence of P1 in DMSO/PBS (1:1, v/v) increases to 2.9-fold after the addition of 50 μM BSA through electrostatic complexation and hydrophobic interaction.
Calix[4]pyrrole-Crosslinked Porous Polymeric Networks for the Removal of Micropollutants from Water
Wang, Xiaohua,Xie, Linhuang,Lin, Kunhua,Ma, Weibin,Zhao, Tian,Ji, Xiaofan,Alyami, Mram,Khashab, Niveen M.,Wang, Hongyu,Sessler, Jonathan L.
, p. 7188 - 7196 (2021)
Calix[4]pyrrole-based porous organic polymers (P1–P3) for removing organic micropollutants from water were prepared. A bowl-shaped α,α,α,α-tetraalkynyl calix[4]pyrrole and diketopyrrolopyrrole monomer were crosslinked via Sonogashira coupling to produce a 3D network polymer, P1. P1 proved too hydrophobic for use as an adsorbent and was converted to the corresponding neutral polymer P2 (containing carboxylic acid groups) and its anionic derivative P3 (containing carboxylate anion groups). Anionic P3 outperformed P2 in screening studies involving a variety of model organic micropollutants of different charge, hydrophilicity and functionality. P3 proved particularly effective for cationic micropollutants. The theoretical maximum adsorption capacity (qmax,e) of P3 reached 454 mg g?1 for the dye methylene blue, 344 mg g?1 for the pesticide paraquat, and 495 mg g?1 for diquat. These uptake values are significantly higher than those of most synthetic adsorbent materials reported to date.
Synthesis and electroluminescence properties of fluorene-co-diketopyrrolopyrrole-co-phenothiazine polymers
Qiao, Zhi,Peng, Junbiao,Jin, Yi,Liu, Qilin,Weng, Jiena,He, Zhicai,Han, Shaohu,Cao, Derong
, p. 1016 - 1023 (2010)
A series of fluorene-co-diketopyrrolopyrrole(DPP)-co-phenothiazine polymers, named as Flu-DPP-Phen, were synthesized by a palladium-catalyzed Suzuki coupling reaction with different feed ratios among 9,9-dihexylfluorene-2,7-bis(trimethylene boronate), 2,5-dioctyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione, and 3,7-dibromo-10-octylphenothiazine. Their chemical structures and compositions were confirmed by 1H NMR and elemental analysis. These terpolymers were found to be thermally stable and readily soluble in common organic solvents. Absorption and photoluminescence (PL) properties of Flu-DPP-Phen exhibit regular change with increasing of DPP contents in the terpolymers. Electroluminescence (EL) properties of all the terpolymers were characterized with the device configurations of ITO/PEDOT/terpolymer/Ba/Al and ITO/PEDOT/PVK/terpolymer/Ba/Al. Owing to exciton confinement on the narrow band gap DPP unit, the emission of fluorene segments is quenched completely with very low content of DPP (0.2 mol%). The EL spectra of all the terpolymers show exclusive long-wavelength emission originating from DPP units, which implied that the energy transfer in the terpolymer is very efficient. EL colors of the terpolymers vary from orange to red, the maximum emission is gradually red-shifted from 582 nm to 600 nm. The best EL performance was achieved by Flu-DPP-Phen(50:30:20) with maximum external quantum efficiency (EQE) of 0.25% and maximum brightness of 259 cd/m2 in the device configuration of ITO/PEDOT/PVK/terpolymer/Ba/Al. The preliminary EL results proved that DPP units could effectively improve the electron affinity, and phenothiazine units could significantly enhance the hole injection ability, which resulted in the remarkable improvement of EQE.
Diketopyrrolopyrrole-containing polyfluorenes: Facile method to tune emission color and improve electron affinity
Cao, Derong,Liu, Qilin,Zeng, Wenjing,Han, Shaohu,Peng, Junbiao,Liu, Shouping
, p. 8347 - 8355 (2006)
A series of novel diketopyrrolopyrrole (DPP)-containing polyfluorenes, coded as PF-DPP01-50, were synthesized through palladium-catalyzed Suzuki polycondensation with different feed ratios between fluorene dibromide and DPP dibromide. Their chemical structures and compositions were verified by 1H NMR and elemental analysis. DSC and TGA results show that they have good to excellent thermal stabilities. Absorption and photoluminescence (PL) properties of PF-DPP01 -50, determined in both CHCl3 solutions and thin films, exhibit regular changes with increasing of DPP contents in copolymers, with absolute PL efficiencies being in the range 13.8-26.9%. Electroluminescence (EL) properties of all the copolymers were investigated with device configurations of ITO/PEDOT/copolymer/Ba/Al and ITO/PEDOT/copolymer/Al. A very low content of DPP units (1 %) is needed to achieve full energy transfer from fluorene segments to DPP units; hence, exclusive emission of the latter occurs. EL colors of these copolymers vary from orange to red, corresponding to CIE coordinates from (0.52, 0.46) to (0.62, 0.37). The best performance was achieved by orange-emitting PF-DPP01 in device configuration of ITO/PEDOT/copolymer/Ba/Al, with maximum EQE of 0.45% and maximum brightness of 520 cd/m2. Devices with configuration of ITO/PEDOT/copolymer/Al prove that DPP units can effectively improve the electron affinity of these copolymers. One of these devices (ITO/PEDOT/PF-DPP25/Al) can realize maximum EQE of 0.14% and maximum brightness of 127 cd/m2. Therefore, color-tuning (red-shift) and improvement of electron affinity can be achieved at the same time through incorporation of DPP units.
Effect of end groups on the band gap of donor-acceptor based small molecules containing diketopyrrolopyrrole
Han, Jin-Hee,Kang, Hun-Min,Song, Dong Jin,Shaik, Baji,Heo, Yu Mi,Chung, Hye Jin,Paek, Seung-Mann
, p. 1040 - 1054 (2017)
(Acceptor-donor-acceptor type compounds 5,5′-(4,4′-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(4,1-phenylene))dithiophene-2-carbonitrile (DPPTCN), 4′,4″-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)dibiphenyl-4-carbonitrile (DPPPhCN), 2,2′-(5,5′-(4,4′-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetra-hydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(4,1-phenylene))bis(thiophene-5,2-diyl))-bis(methan-1-yl-1-ylidene)dimalononitrile (DPPT2CN), 2,2′-(4′,4″-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(biphenyl-4′,4-diyl))bis(methan-1-yl-1-ylidene)dimalononitrile (DPPPh2CN) were designed and synthesized. All the compounds have central diketopyrrolopyrrole common acceptor unit, the donor groups differ either thiophene or phenyl group and the terminal end groups are differ either nitrile or dicyanovinylene groups. In order to study the relationship between chemical structure and properties, their optical, thermal and electrochemical properties were investigated. Thermal properties indicate that all the compounds have high thermal stability. Among DPPT2CN with thiophene groups as donor and dicyanovinylene as acceptor has shown lowest LUMO energy level of -3.77 eV and low HOMO-LUMO band gap 1.86 eV.
DPP based dual-sensing probe for the multi-color detection of toxic Co2+/Sn2+ and CN? ions in water: An electronic eye development
Manivannan, Ramalingam,Ryu, Jiwon,Son, Young-A
, (2021/05/13)
A dual-sensing mechanism probe for the multi-color detection of toxic Co2+/Sn2+ and CN? ions in water based on a diketopyrrolopyrrole (DPP) moiety was designed and successfully synthesized. Colorimetric and fluorimetric methods were used to confirm the sensing performance of the probe. Different colors were achieved for the detecting ions Co2+, Sn2+, and CN?. pink for Co2+, red for Sn2+, and colorless for CN?, denoting high selectivity in the developed probe. A dual-sensing mechanism confirmed for the metal ion the sensing is via complexation resulting in color (different) change through metal to ligand charge-transfer transition (MLCT), and for anion (cyanide), it is through addition reaction with a disconnection in intramolecular charge-transfer transition (ICT). Pre-added selected ions to the different water samples effectively detect different colors. We developed an electronic eye (RGB - Arduino device) for the detection of toxic ions effectively.
An Electron-Accepting aza-BODIPY-Based Donor–Acceptor–Donor Architecture for Bright NIR Emission
Kage, Yuto,Kang, Seongsoo,Mori, Shigeki,Mamada, Masashi,Adachi, Chihaya,Kim, Dongho,Furuta, Hiroyuki,Shimizu, Soji
supporting information, p. 5259 - 5267 (2021/02/26)
A bright near-infrared (NIR) fluorescent molecule was developed based on the donor–acceptor–donor (D–A–D) approach using an aza-BODIPY analog called pyrrolopyrrole aza-BODIPY (PPAB) as an electron-accepting chromophore. Directly introducing electron-donating triphenylamine (TPA) to develop a D–A–D structure caused redshifts of absorption and emission of PPAB into the NIR region with an enhanced fluorescence brightness of up to 5.2×104 m?1 cm?1, whereas inserting a phenylene linker between the TPA donor and the PPAB acceptor induced solvatochromic behavior in emission. Transient absorption spectra and theoretical calculations revealed the presence of a highly emissive hybridized locally excited and charge-transfer state in the former case and the contribution of the dark charge-separated state to the excited state in the latter case. The bright D–A–D PPAB as a novel emitter resulted in a NIR electroluminescence with a high external quantum efficiency of 3.7 % and a low amplified spontaneous emission threshold of ca. 80 μJ cm?2, indicating the high potential for NIR optoelectronic applications.
Dimethyl Sulfoxide-Free and Water-Soluble Fluorescent Probe for Detection of Bovine Serum Albumin Prepared by Ionic Co-assembly of Amphiphiles
Tong, Qin,Wu, Weichun,Hu, Jianghong,Wang, Junhao,Li, Ke,Dong, Bin,Song, Bo
, p. 4532 - 4539 (2021/05/07)
Detection of bovine serum albumin (BSA) is an important issue in the sense of medical applications and enzymatic reactions; however, the recently developed fluorescent probes require the involvement of dimethyl sulfoxide (DMSO), which may be detrimental to proteins. In this study, we demonstrated a DMSO-free and water-soluble fluorescent probe prepared by ionic co-assembly of amphiphiles. The cationic amphiphile is a newly designed molecule (denoted by DPP-12) bearing a conjugated diketopyrrolopyrrole (DPP) and two tetraphenylethylene groups. It turns out that the fluorescence emission of DPP-12 depends on the amount of anionic amphiphilic sodium dodecyl benzene sulfonate (SDBS). The fluorescence intensity first increases and then decreases with the concentration of SDBS, and each branch presents a linear relationship. BSA consumes SDBS by the formation of complexes, thus leading to an increase of fluorescence intensity of the mixed solution of DPP-12 and SDBS. Therefore, the mixed solution of DPP-12 and SDBS was applied as a fluorescent probe to detect the low concentration of BSA by back-titration. This fluorescent probe does not require DMSO and has good tolerance to metal ions in blood and good photostability. The limit of detection is as low as 940 nM, almost 3 orders of magnitude lower than the content in organisms.
COLORING COMPOSITION, FILM, COLOR FILTER, METHOD FOR MANUFACTURING COLOR FILTER, SOLID-STATE IMAGING ELEMENT, AND IMAGE DISPLAY DEVICE
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Paragraph 0368-0370, (2021/08/20)
Provided are a coloring composition including a pigment, a pigment derivative, and a resin, in which an average primary particle diameter of the pigment is 70 nm or less, and an average primary particle diameter of the pigment derivative is more than 70 nm; a film formed of a coloring composition; a color filter; a method for manufacturing a color filter; a solid-state imaging element; and an image display device.
COLORING COMPOSITION, FILM, COLOR FILTER, METHOD FOR MANUFACTURING COLOR FILTER, STRUCTURE BODY, SOLID-STATE IMAGING ELEMENT, AND IMAGE DISPLAY DEVICE
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Paragraph 0406-0407, (2021/07/24)
Provided are a coloring composition including a pigment, a pigment derivative, a resin, and a solvent, in which an average primary particle diameter of the pigment is 70 nm or less, an average primary particle diameter of the pigment derivative is 70 nm or less, and the solvent includes a solvent D1 having a solubility parameter of 18.0 to 26.0 MPa0.5; a film formed of a coloring composition; a color filter; a method for manufacturing a color filter; a structure body; a solid-state imaging element; and an image display device.
