Keep glowing and going: recent progress in diketopyrrolopyrrole synthesis towards organic optoelectronic materials

Luo, Nan; Zhang, Guanxin; Liu, Zitong

doi:10.1039/d1qo00613d

Cited by 36 publications

(26 citation statements)

References 145 publications

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“…DPP unit was obtained by the typically exploited succinic strategy: [1] 2‐cyanothiophene was reacted with diisopropylsuccinate in a strongly basic environment at 130 °C and product 1 was obtained with 80 % yield. 1 was then N‐functionalized through the reaction 1‐bromo‐2‐octyldodecane (in turn prepared from the reaction of the corresponding alcohol with bromine/PPh3 in a classical Appel reaction) at high temperature in dimethylformamide (DMF) and in presence of K 2 CO 3 as base, with 28 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…DPP unit was obtained by the typically exploited succinic strategy: [1] 2-cyanothiophene was reacted with diisopropylsuccinate in a strongly basic environment at 130 °C and product 1…”

Section: Chemical Physical Characterizationmentioning

confidence: 99%

“…Diketopyrrolopyrrole (DPP) derivatives represent a class of molecular systems that have been widely investigated and employed in several applications of relevant technological appeal. [1][2][3][4][5][6][7] The DPP core structure was synthesized for the first time in the early 1970s. [8] Due to some outstanding properties such as beautiful and brilliant colour (ranging from orange to bluish red), high thermal stability and excellent photophysical properties, DPP derivatives are nowadays among the most important high-performance pigments, used in the fields of inks and paints, automotive industry, plastics and fibers.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel Thienyl DPP derivatives Functionalized with Terminal Electron‐Acceptor Groups: Synthesis, Optical Properties and OFET Performance

Fusco

Barra²,

Gontrani

et al. 2022

Chemistry A European J

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Three novel diketopyrrolopyrrole (DPP) based small molecules have been synthesized and characterized in terms of their chemical‐physical, electrochemical and electrical properties. All the molecules consist of a central DPP electron acceptor core symmetrically functionalized with donor bi‐thienyl moieties and flanked in the terminal positions by three different auxiliary electron‐acceptor groups. This kind of molecular structure, characterized by an alternation of electron acceptor and donor groups, was purposely designed to provide a significant absorption at the longer wavelengths of the visible spectrum: when analysed as thin films, in fact, the dyes absorb well over 800 nm and exhibit a narrow optical bandgap down to 1.28 eV. A detailed DFT analysis provides useful information on the electronic structure of the dyes and on the features of the main optical transitions. Organic field‐effect transistors (OFETs) have been fabricated by depositing the DPP dyes as active layers from solution: the different end‐functionalization of the dyes had an effect on the charge‐transport properties with two of the dyes acting as n‐type semiconductors (electron mobility up to 4.4 ⋅ 10−2 cm2/V ⋅ s) and the third one as a p‐type semiconductor (hole mobility up to 2.3 ⋅ 10−3 cm2/V ⋅ s). Interestingly, well‐balanced ambipolar transistors were achieved by blending the most performant n‐type and p‐type dyes with hole and electron mobility in the order of 10−3 cm2/V ⋅ s

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Section: Resultsmentioning

confidence: 99%

“…DPP unit was obtained by the typically exploited succinic strategy: [1] 2-cyanothiophene was reacted with diisopropylsuccinate in a strongly basic environment at 130 °C and product 1…”

Section: Chemical Physical Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel Thienyl DPP derivatives Functionalized with Terminal Electron‐Acceptor Groups: Synthesis, Optical Properties and OFET Performance

Fusco

Barra²,

Gontrani

et al. 2022

Chemistry A European J

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“…They strongly absorb visible light, show significant electron-withdrawing effects, and possess high electron mobility. [8][9][10][11][12] Due to these properties, DPPs are often used as an electron-acceptor unit to design optoelectronic devices 13,14 such as new push-pull polymers, 15,16 organic light-emitting diodes, 17 and more recently, singletfission chromophores. 8,18,19 Motivated by the design of new intramolecular singlet-fission materials, Mukhopadhyay et al 20 proposed a combination of a thiophene-DPP derivative (with charge-transfer (CT) character) with a vinyl linker (polyene character) (Figure 1b).…”

Section: Introductionmentioning

confidence: 99%

Using diketopyrrolopyrroles to stabilize double excitation and control internal conversion

Casal

Toldo

Plasser

et al. 2022

Preprint

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Diketopyrrolopyrrole (DPP) is a pivotal functional group to tune the physicochemical properties of novel organic photoelectronic materials. Among its multiple uses, DPP-thiophene derivatives forming a dimer through a vinyl linker were recently shown to quench the fluorescence observed in their isolated monomers. Here, we explain this fluorescence quenching using computational chemistry. The DPP-thiophene dimer has a low-lying doubly excited state that is not energetically accessible for the monomer. This state delays the fluorescence allowing internal conversion to occur first. We characterize the doubly excited state wavefunction by systematically changing the derivatives to tune the pi-scaffold size and the acceptor and donor characters. The origin of this state's stabilization is related to the increase in the π-system and not to the charge-transfer features. This analysis delivers core conceptual information on the electronic properties of organic chromophores arranged symmetrically around a vinyl linker, opening new ways to control the balance between luminescence and internal conversion.

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Pre‐Endcapping of Hyperbranched Polymers toward Intrinsically Stretchable Semiconductors with Good Ductility and Carrier Mobility

Zhou,

Luo,

Cui

et al. 2024

Advanced Materials

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The advancement of semiconducting polymers stands as a pivotal milestone in the quest to realize wearable electronics. Nonetheless, endowing semiconductor polymers with stretchability without compromising their carrier mobility remains a formidable challenge. This study proposes a “pre‐endcapping” strategy for synthesizing hyperbranched semiconducting polymers (HBSPs), aiming to achieve the balance between carrier mobility and stretchability for organic electronics. The findings unveil that the aggregates formed by the endcapped hyperbranched network structure not only ensure efficient charge transport, but also demonstrate superior tensile resistance. In comparison to linear conjugated polymers, HBSPs exhibit substantially larger crack onset strains and notably diminished tensile moduli. It is evident that the HBSPs surpass their linear counterparts in terms of both their semiconducting and mechanical properties. Among HBSPs, HBSP‐72h‐2.5 stands out as the preeminent candidate within the field of inherently stretchable semiconducting polymers, maintaining 93% of its initial mobility even when subjected to 100% strain (1.41±0.206 cm2V−1s−1). Furthermore, thin film devices of HBSP‐72h‐2.5 remain stable after undergoing repeated stretching and releasing cycles. Notably, the mobilities are independent of the stretching directions, showing isotropic charge transport behavior. The preliminary study makes this “pre‐endcapping” strategy a potential candidate for future design of organic materials for flexible electronic devices.This article is protected by copyright. All rights reserved

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Keep glowing and going: recent progress in diketopyrrolopyrrole synthesis towards organic optoelectronic materials

Abstract: Diketopyrrolopyrrole (DPP) and its derivatives are commercially used dyes that have drawn great attention in recent years for applications in organic electronic/optical materials. These material studies cannot progress without further...

Cited by 36 publications

References 145 publications

Novel Thienyl DPP derivatives Functionalized with Terminal Electron‐Acceptor Groups: Synthesis, Optical Properties and OFET Performance

Novel Thienyl DPP derivatives Functionalized with Terminal Electron‐Acceptor Groups: Synthesis, Optical Properties and OFET Performance

Using diketopyrrolopyrroles to stabilize double excitation and control internal conversion

Pre‐Endcapping of Hyperbranched Polymers toward Intrinsically Stretchable Semiconductors with Good Ductility and Carrier Mobility

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