Synthesis of diketopyrrolopyrrole (DPP) derivatives comprising bithiophene moieties

Stas, Sara; Sergeyev, Sergey; Geerts, Yves

doi:10.1016/j.tet.2010.01.027

Cited by 52 publications

(41 citation statements)

References 35 publications

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“…[ 2a ] The possibility that such compounds would form was fi rst noticed by Geerts and co-workers, who performed the alkylation of DPP and, in addition to the expected N , N -dialkyl derivative, separated two additional dyes from the reaction mixture. [ 31 ] The authors concluded that these may be O -alkyl derivatives, but due to the contamination of the samples, they failed to provide conclusive evidence. …”

Section: Reaction With Amide Groups Of Dpps As Nucleophilesmentioning

confidence: 99%

“…This is due to the fact that, under strongly basic conditions, bromine atoms in such nitriles readily undergo nucleophilic substitution, which decreases the yields and complicates the purifi cation process of the desired products. [ 31 ] Our laboratory provides another example of the electrophilic aromatic substitution taking place at aryl substituents in DPP derivatives. DPPs with relatively electron-rich aromatic substituents can be alkylated with bromoacetaldehyde diethyl acetal in DMF using K 2 CO 3 as a base and tetrabutylammonium bisulfate as a PTC catalyst ( Scheme 37 ).…”

Section: Reviewmentioning

confidence: 99%

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Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Grzybowski

Gryko

2015

Advanced Optical Materials

324

293

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First reported by Farnum as much as 40 years ago, diketopyrrolopyrroles (2,5‐dihydropyrrolo[4,3‐c]pyrrolo‐1,4‐diones) are currently one of the most widely used dyes, with applications that span high‐quality pigments, field‐effect transistors, bulk‐heterojunction solar cells, dye‐sensitized solar cells, and fluorescence imaging. Due to the breadth of their utility, there have been several focused reviews on this topic since 1988. Considering the growing importance of these dyes, this review describes the overall progress made in four decades in both synthesis and the elucidation of their reactivity, and offers a critical comparison of various methods reported in the literature. The relationship between their structure and optical properties is also reviewed in detail. The extension of diketopyrrolopyrroles' chromophore leads to a significant change in both linear and nonlinear optical properties. A very strong bathochromic shift in the absorption and an increase in the two‐photon absorption cross‐section are typical for these analogues. Straightforward synthesis combined with good stability and a near‐unity fluorescence quantum yield ensures that diketopyrrolopyrroles will continue to attract attention for years to come. The goal of this review is to systematize knowledge on these dyes, enabling their use in more real‐world applications.

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Section: Reaction With Amide Groups Of Dpps As Nucleophilesmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Grzybowski

Gryko

2015

Advanced Optical Materials

324

293

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“…Numerous papers have been published by researchers worldwide on synthesis and experimental study of small oligothiophene‐flanked DPP molecules . For instance, for a series of DPP molecules symmetrically disubstituted with oligothiophenes, it was shown that electrochemical properties were affected to a significant extent by the length of oligothiophene units and the position of the substituent in it, but were independent of the type of alkyl N‐substituent .…”

Section: Introductionmentioning

confidence: 99%

Computational study of structure, electronic, and microscopic charge transport properties of small conjugated diketopyrrolopyrrole‐thiophene molecules

Макарова

Semenov

Guskova

2016

Int J of Quantum Chemistry

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π‐Conjugated small molecules containing diketopyrrolopyrrole (DPP) and thiophene moieties represent a modern class of functional materials that exhibit promising charge transport properties and therefore have great potential as building blocks of active elements of electronic devices. As a starting point of this computational study, the molecular structure, electronic characteristics, and reorganization energies associated with electron or hole transfer are considered. Prediction of molecular crystal packing is followed by the calculation of couplings between adjacent molecules and detection of the effective charge transfer pathways. Finally, the rates of charge transfer process are evaluated. The obtained results shed light not only on the properties of materials containing low‐molecular species but also serve as a benchmark for further classical force‐field simulations of DPP‐based polymers.

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“…2‐Hexyldecyl bromide ( 1 ), 1,2‐di(thiophen‐3‐yl)ethane‐1,2‐dione ( 4 ), benzo[1,2‐ b :6,5‐ b ′]dithiophene‐4,5‐dione ( 5 ), and 2,7‐dibromo‐benzo[1,2‐ b :6,5‐ b ′]dithiophene‐4,5‐dione ( 6 ) were synthesized in accordance with the literature. 4,8‐Bis[5‐(2‐ethylhexyl)‐2‐thienyl]‐benzo[1,2‐ b :4,5‐ b ′]dithiophene remained from previous studies …”

Section: Methodsmentioning

confidence: 99%

Dithienobenzimidazole‐containing conjugated donor–acceptor polymers: Synthesis and characterization

Harris

Stihl

Schmidt

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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The synthesis of two new conjugated polymers based on the relatively under‐exploited monomer, 5,8‐dibromo‐2‐[5‐(2‐hexyldecyl)‐2‐thienyl]‐1H‐dithieno[3,2‐e:2′,3′‐g]benzimidazole (dithienobenzimidazole, DTBI), and either 4,7‐bis[4‐hexyl‐5‐(trimethylstannyl)‐2‐thienyl]‐2,1,3‐benzothiadiazole (BTD) or 2,6‐bis(trimethylstannyl)‐4,8‐bis(5‐(2‐ethylhexyl) thiophen‐2‐yl)benzo[1,2‐b:4,5‐b′]dithiophene (BDT) is described. The polymers were synthesized via Stille polycondensation and characterized by traditional methods (1H NMR, gel‐permeation chromatography, matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry, thermal gravimetric analysis, differential scanning calorimetry, ultraviolet–visible spectroscopy, photoluminescence, and cyclic voltammetry). Prior to their synthesis, trimer structures were modeled by DFT calculations facilitating a further understanding of the systems' electronic and geometric structure. Polymers were titrated with acid and base to take advantage of their amphiprotic imidazole moiety and their optical response monitored with ultraviolet–visible spectroscopy. Finally, pristine polymer thin‐films were treated with acid and base to evaluate (de)protonation's effect on system electronics, but thin‐film degradation was encountered. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 60–69

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Synthesis of diketopyrrolopyrrole (DPP) derivatives comprising bithiophene moieties

Cited by 52 publications

References 35 publications

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Computational study of structure, electronic, and microscopic charge transport properties of small conjugated diketopyrrolopyrrole‐thiophene molecules

Dithienobenzimidazole‐containing conjugated donor–acceptor polymers: Synthesis and characterization

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