Lactam analogues of pentalene. A new one-pot synthesis of pyrrolo[3,2-b]pyrrole-2,5-diones deriving from pulvinic acid

Wuckelt, Jörg; Döring, Manfred; Langer, Peter; Görls, Helmar; Beckert, Rainer

doi:10.1016/s0040-4039(97)01148-9

Cited by 21 publications

(14 citation statements)

References 10 publications

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“…However, the important physical properties of the isoDPPs, such as brilliant red color and high melting points were unnoticed. In 1997, J. Wuckelt et al took notice of this compound and found an efficient strategy to synthesize isoDPP in a single reaction step with a high yield of up to 75% when a benzene unit substituted R1 and R2 (Scheme 1) [18]. The formation of product isoDPP involves two-fold attack of 2 equivalent of the ester enolate onto the bis(imidoyl)chloride to obtain the open-chained intermediate A, which rapidly equilibrates with the enamine-tatuometres B, C, and D. P. Langer further proved this method [25].…”

Section: Small Molecules and Monomersmentioning

confidence: 99%

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Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Deng

et al. 2019

Polymers

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π-Conjugated organic donor–acceptor (D–A) type polymers are widely developed and used in electronic device. Among which, diketopyrrolopyrrole (DPP)-based polymers have received the most attention due to their high performances. The novel chromophores named 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), benzodipyrrolidone (BDP) and naphthodipyrrolidone (NDP) are resemble DPP in chemical structure. IsoDPP is an isomer of DPP, with the switching position of carbonyl and amide units. The cores of BDP and NDP are tri- and tetracyclic, whereas isoDPP is bicyclic. π-Conjugation extension could result polymers with distinct optical, electrochemical and device performance. It is expected that the polymers containing these high-performance electron-deficient pigments are potential in the electronic device applications, and have the potential to be better than the DPP-based ones. IsoDPP, BDP, and NDP based polymers are synthesized since 2011, and have not receive desirable attention. In this work, the synthesis, properties (optical and electrochemical characteristics), electronic device as well as their relationship depending on core-extension or structure subtle optimization have been reviewed. The final goal is to outline a theoretical scaffold for the design the D–A type conjugated polymers, which is potential for high-performance electronic devices.

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Section: Small Molecules and Monomersmentioning

confidence: 99%

“…Altering the position of carbonyl and amide units of the DPP pigment result an isomer of DPP, named 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP, Figure 2). IsoDPP chromophore exhibit deep color, weather resistance, strong π-stacking, high electron mobility (μ e ), and good chemical-, thermal-, and photo-stability [18].…”

Section: Introductionmentioning

confidence: 99%

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Deng

et al. 2019

Polymers

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“…One of them is constructed of six isocyanide groups which are coupled at a palladium center. Compounds with two carbonyl functions at the C-2 and C-5 positions of the heterocycle may be produced by a one-pot reaction from bis-imidoyl chlorides of oxalic acid and monoanions of acetic acid ester derivatives (Wuckelt et al, 1997). If the same reaction is performed under a CO atmosphere one of the imine functions is replaced by a carbonyl group (Tanase et al, 1996).…”

Section: Commentmentioning

confidence: 99%

1,4,N-Tri-tert-butyl-2,5-bis-tert-butylimino-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrol-3-amine

2006

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“…Hence, there is considerable scope for this moiety to be explored as a component of a range of materials and their application in various organic electronic devices. The IsoDPP moiety is a part of the structure of a natural dye that is found in lichens [ 22 ]. The difference between the chemical structures of DPP and IsoDPP are in the positions of the carbonyl group and nitrogen atom, which are switched.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells

et al. 2020

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We introduce two novel solution-processable electron acceptors based on an isomeric core of the much explored diketopyrrolopyrrole (DPP) moiety, namely pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP). The newly designed and synthesized compounds, 6,6′-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione] (NAI-IsoDPP-NAI) and 5,5′-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)isoindoline-1,3-dione] (PI-IsoDPP-PI) have been synthesized via Suzuki couplings using IsoDPP as a central building block and napthalimide or phthalimide as end-capping groups. The materials both exhibit good solubility in a wide range of organic solvents including chloroform (CF), dichloromethane (DCM), and tetrahydrofuran (THF), and have a high thermal stability. The new materials absorb in the wavelength range of 300–600 nm and both compounds have similar electron affinities, with the electron affinities that are compatible with their use as acceptors in donor-acceptor bulk heterojunction (BHJ) organic solar cells. BHJ devices comprising the NAI-IsoDPP-NAI acceptor with poly(3-n-hexylthiophene) (P3HT) as the donor were found to have a better performance than the PI-IsoDPP-PI containing cells, with the best device having a VOC of 0.92 V, a JSC of 1.7 mAcm−2, a FF of 63%, and a PCE of 0.97%.

show abstract

Lactam analogues of pentalene. A new one-pot synthesis of pyrrolo[3,2-b]pyrrole-2,5-diones deriving from pulvinic acid

Cited by 21 publications

References 10 publications

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

1,4,N-Tri-tert-butyl-2,5-bis-tert-butylimino-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrol-3-amine

Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells

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