54660-00-3Relevant articles and documents
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.
Diketopyrrolopyrrole Bis-Phosphonate Conjugate: A New Fluorescent Probe for In Vitro Bone Imaging
Chiminazzo, Andrea,Borsato, Giuseppe,Favero, Alessia,Fabbro, Chiara,McKenna, Charles E.,Dalle Carbonare, Luca Giuseppe,Valenti, Maria Teresa,Fabris, Fabrizio,Scarso, Alessandro
supporting information, p. 3617 - 3626 (2019/02/19)
The synthesis of a conjugate molecule between an unusual red-fluorescent diketopyrrolopyrrole (DPP) unit and a bis-phosphonate (BP) precursor by a click-chemistry strategy to target bone tissue and monitor the interaction is reported. After thorough investigation, conjugation through a triazole unit between a γ-azido rather than a β-azido BP and an alkyne-functionalized DPP fluorophore group turned out to be the winning strategy. Visualization of the DPP-BP conjugate on osteoclasts and specific antiresorption activity were successfully demonstrated.
Rational synthesis and comparative investigation on a series of fluorinated aryl substituted diketopyrrolopyrrole
Xu, Jie,Zhang, Shaoze,Wu, Shengying,Bi, Shiming,Li, Xinjin,Lu, Yunxiang,Wang, Limin
, p. 494 - 499 (2017/01/14)
We novelly designed and synthesized a set of fluorinated diphenyl-diketopyrrolopyrrole (DPP) compounds by varying the position and amount of fluorine atom, and to the best of our knowledge, it is the first time a difluoromethyl group and perfluoroalkyl ch
A Thienyl-Substituted Diketopyrrolopyrrole Derivative with Efficient Reactive Oxygen Species Generation for Photodynamic Therapy
Shi, Huaxia,Sun, Wucheng,Wang, Qiang,Gu, Guiying,Si, Weili,Huang, Wei,Zhang, Qi,Dong, Xiaochen
, p. 515 - 520 (2016/07/06)
Reducing the energy gap of photosensitizer between singlet and triplet states (ΔEST) can improve the efficiency of intersystem crossing, further enhancing the resulting generation of reactive oxygen species for photodynamic therapy. In this study, two photosensitizer chromophores—phenyl-substituted diketopyrrolopyrrole and thienyl-substituted diketopyrrolopyrrole (TDPP)—were synthesized. Theoretical calculations indicate that TDPP can greatly reduce the ΔEST (0.48 eV) relative to that of diketopyrrolopyrrole (0.66 eV). Experiments confirmed that TDPP generates reactive oxygen species more efficiently than diketopyrrolopyrrole. After conjugation of TDPP with methoxy poly(ethylene glycol)carboxyl (mPEG-COOH), the resulting TDPP-mPEG has excellent water solubility, biocompatibility and photostability. When it serves as photosensitizer for photodynamic therapy, in vitro and in vivo measurements indicate that TDPP-mPEG can effectively inhibit tumor growth and shows great potential for the treatment of cancer in the clinic.
Fluorine Directed Two-Dimensional Cruciform π-π Stacking in Diketopyrrolopyrroles
Calvo-Castro, Jesus,Morris, Graeme,Kennedy, Alan R.,McHugh, Callum J.
, p. 5385 - 5393 (2016/11/15)
Enhanced bulk dimensionality in organic materials employed in optoelectronic devices is desirable and can overcome fabrication issues related to structural defects and grain boundaries. Herein, we report a novel fluorinated diketopyrrolopyrrole single cry
Highly fluorescent and water-soluble diketopyrrolopyrrole dyes for bioconjugation
Heyer, Elodie,Ziessel, Raymond,Lory, Pauline,Moreau, Mathieu,Romieu, Anthony,Leprince, Jrme,Guardigli, Massimo,Roda, Aldo
supporting information, p. 2995 - 2999 (2015/05/27)
The preparation of highly water-soluble and strongly fluorescent diketopyrrolopyrrole (DPP) dyes using an unusual taurine-like sulfonated linker has been achieved. Exchanging a phenyl for a thienyl substituent shifts the emission wavelength to near λ = 600 nm. The free carboxylic acid group present in these new derivatives was readily activated and the dyes were subsequently covalently linked to a model protein (bovine serum albumin; BSA). The bioconjugates were characterized by electronic absorption, fluorescence spectroscopy and MALDI-TOF mass spectrometry, thus enabling precise determination of the labeling density (ratio DPP/BSA about 3 to 8). Outstanding values of fluorescence quantum yield (30% to 59%) for these bioconjugates are obtained. The photostability of these DPP dyes is considerably greater than that of fluorescein under the same irradiation conditions. Remarkably low detection limits between 80 and 300 molecules/μm2 were found for the BSA bioconjugates by fluorescence imaging with a epifluorescence microscope.
An efficient pathway to synthesize diketopyrrolopyrrole pigments in ionic liquids
Nourmohammadian, Farahnaz,Shamekhi, S. Shiva
, p. 131 - 138 (2013/07/26)
The investigation results of an efficient pathway for the synthesis of high-performance 1, 4-diketo-3, 6-diphenyl pyrrolo [3, 4-c] pyrroles pigments using diethyl succinate in ionic liquids ([BMIM][BF4], and [HMIM][BF4]) has been reported. Synthesis of 3, 6-Bis (4-chlorophenyl)-2, 5-dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione using [BMIM][BF4] is more efficient (81% at 30°C) than conventional methods (70% at 105-110°C). 3, 6-Bis (4-bromophenyl)-2, 5-dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione was produced in this approach with 73% yield at 30°C in 8 h reaction time instead of the previously reported (65% yield in 24 h). The production yield of 1, 4-diketo-3, 6-diphenyl pyrrolo [3, 4-c] pyrroles was not highly affected by ionic liquids, and produced in maximum 43% yield. The crystalline phase, particle sizes and morphologies of the synthesized pigments have also been reported.
IMPROVED, RED COLOUR FILTER COMPOSITION
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Page/Page column 40-41, (2009/12/27)
A composition, for producing dispersions, thermoplastic masses and/or colour filters, comprising (a) a colourant of formula (1) wherein 20-100 mol% R1 are Br and 80-100 mol% R3 are H, especially of formula (Ib) and /or (Ic); (b) from 0 to 150 % by weight, based on (a), of C. I. Pigment Red 144, 188, 190, 224, 242 or 2,4,6-trimethylphenylperylene diimide; (c) from 3 to 25 % by weight, based on (a), of a di- or tri-azacyclopentylmethyl-substituted colourant (formulae given); (d) from 0 to 10 % by weight, preferably from 0.01 to 8 % by weight, based on the sum of (a) and (b), of an additionally sulfonated colourant of the same kernels as in (c); and (e) from 0 to 30 % by weight, preferably from 3 to 25 % by weight, especially from 5 to 20 % by weight, based on (a), of a diketopyrrolopyrrole colourant substituted by at least one chain containing a plurality of nitrogen atoms (cf. formula (V)). The compound of formula (Ig), wherein R20 and R22 are, each independently of the other, H, Cl, Br, CN, CF3, R22, OR22, SR22, SOR22, SO2R22, NR23COR22, COOR23, CONR22R23, CONH2, CON(R22)2 or CON(R24), preferably Cl, Br, CN or R22, wherein R22, in each case independently of any other R22, is C1-C5alkyl, C2-C5alkylene, phenyl or 2-naphthyl, preferably methyl or phenyl, R23, in each case independently of any other R23, is H, d-C5alkyl or C2-C5alkylene, preferably H Or CH3, and R24, in each case independently of any other R24, is C4-C8alkylene which is uninterrupted or interrupted one or more times by NR23, NOR23, O, S, SO or by SO2, R24 in N(R24) forming with N a preferably 5- or 6-membered heterocyclic ring, with the proviso that R20 and R21 are not simultaneously Br and H, respectively, and also solid solutions thereof are likewise claimed. Also claimed is the compound of formula (Vb), wherein R27 is Br, Cl, F or methyl, R28 is H, C1-alkyl, or C6-C12alkyl wherein a carbon atom has been replaced by a nitrogen atom, and R29 is C6-C18alkyl wherein 1 or 2 carbon atoms has/have been replaced by nitrogen atom(s).
SOLVENT-FREE PROCESS FOR THE PREPARATION OF DIKETOPYRROLOPYRROLE DERIVATIVES
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Page 18, (2010/02/08)
The present application relates to compounds of formula A(D)X(E)y, (I), compounds of formula (III), compounds of formula (X), as well as processes for the preparation thereof, processes where the compounds (I) are converted to pigments of formula (II) and the use of the compounds (I).
Direct preparation of pyrrolo[3,4-C]pyrroles
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Page column 14-15, (2008/06/13)
A process is disclosed for the direct preparation of pigmentary 1,4-diketopyrrolo-[3,4-c]pyrroles of the formula (I) wherein each of R1and R2independently of the other is an isocyclic or heterocyclic aromatic radical, which process comprises heating an appropriate molar ratio of a disuccinate with a nitrile of the formula (II) R1—CN??(II) or of the formula (III) R2—CN??(III) or with mixtures of said nitrites, in an organic solvent and in the presence of a strong base and an effective amount of a selected particle growth inhibitor of formula (IV)-(X), and then obtaining the compound of formula (I) from the reaction product by protolysis. The process yields pigmentary 1,4-diketopyrrolo-[3,4-c]pyrroles directly, i.e., without the need for additional particle-size reducing aftertreatments. Also disclosed is a composition comprising a pigmentary 1,4-diketopyrrolo-[3,4-c]pyrrole and the particle growth inhibitor. These pigment compositions are useful for pigmenting high molecular weight organic materials.
