84632-54-2Relevant articles and documents
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.
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.
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.
Synthesis, photophysical, electrochemical and computational study of indolocarbazole based donor acceptor type conjugated polymers
Vishnumurthy,Girish
, p. 1969 - 1980 (2021/01/07)
This research reports the synthesis and characterization of two new donor–acceptor type conjugated polymers carrying indolocarbazole as donor, benzothiadiazole and diketopyrrolopyrrole as acceptor via stille coupling polymerization reactions. The structures of the polymer were established by spectroscopic techniques and polymer molecular weight by gel permeation chromatography. Further the linear optical and electrochemical properties of the polymers have been investigated. Polymers showed broad absorption and good fluorescence behaviour with good quantum yields. Optical bandgaps of the polymers were estimated using UV–visible absorption edge and found to be 2.34 and 2.12?eV respectively. Further, theoretical evaluation of the polymers was carried using density functional theory to investigate their geometrical, electrochemical and optical properties using DFT/B3LYP. The obtained results are in good agreement with the experimental results.
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.
