Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors

Głowacki, Eric Daniel; Coskun, Halime; Blood-Forsythe, Martin; Monkowius, Uwe; Leonat, Lucia; Grzybowski, Marek; Gryko, Daniel T.; White, Matthew S.; Aspuru‐Guzik, Alán; Sariciftci, Niyazi Serdar

doi:10.1016/j.orgel.2014.09.038

Cited by 106 publications

(96 citation statements)

References 41 publications

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“…As in the case of other H-bonded pigment semiconductors, it is concluded that charge transport primarily occurs perpendicular to the H-bonding plane, along the two π-stacking directions. It cannot be excluded that, as was recently proposed for close H-bond interactions in diketopyrrolopyrrole compounds, [ 22 ] that a signifi cant probability of charge transport along the H-bonded chains also exists. The short H-bond lengths and close stacking interactions are together accountable for the high crystal lattice energy of epindolidione pigments, as observed by thermogravimetric (TGA) analysis ( Figure 3 ).…”

Section: Crystal Structurementioning

confidence: 92%

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

Głowacki

Romanazzi

Yumusak

et al. 2014

Adv Funct Materials

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1wileyonlinelibrary.com IntroductionHydrogen-bonded organic pigments are a class of materials familiar from applications in the colorant industry, where they fi nd widespread use as materials for robust outdoor paints, cosmetics, and printing inks. [ 1,2 ] Indigo, a natural product, is the oldest and still most widely produced organic dye and pigment ( Figure 1 ). [ 3 ] The intermolecular -NH … O = hydrogen bonding that characterizes indigo is exploited in most of the synthetic hydrogen-bonded pigments as well. This class of materials has proven to be nontoxic and safe for humans, and is considered safer than even several classes of food dyes. [ 4 ] Hydrogen-bonding as a supramolecular engineering tool is useful to control self-assembly and highly relevant to aqueous and biochemical systems. [ 5,6 ] Recently, we have found that indigo, [ 7 ] and some of its derivatives [ 8,9 ] demonstrate ambipolar transport in organic fi eldeffect transistors (OFETs), with mobility ranging from 0.01-0.4 cm 2 V -1 s -1 . We Epindolidiones-Versatile and Stable Hydrogen-Bonded Pigments for Organic Field-Effect Transistors and Light-Emitting DiodesEric Daniel Głowacki , * Giuseppe Romanazzi , Cigdem Yumusak , Halime Coskun , Uwe Monkowius , Gundula Voss , Max Burian , Rainer T. Lechner , Nicola Demitri , Günther J. Redhammer , Nevsal Sünger , Gian Paolo Suranna and Serdar Sariciftci Hydrogen-bonded pigments are remarkably stable high-crystal lattice energy organic solids. Here a lesser-known family of compounds, the epindolidiones, which demonstrates electronic transport with extraordinary stability, even in highly demanding aqueous environments, is reported. Hole mobilities in the range 0.05-1 cm 2 V -1 s -1 can be achieved, with lower electron mobilities of up to 0.1 cm 2 V -1 s -1 . To help understand charge transport in epindolidiones, X-ray diffraction is used to solve the crystal structure of 2,8-difl uoroepindolidione and 2,8-dichloroepindolidione. Both derivatives crystallize with a linear-chain H-bonding lattice featuring two-dimensional π-π stacking. Powder diffraction indicates that the unsubstituted epindolidione has very similar crystallinity. All types of epindolidiones measured here display strong low-energy optical emission originating from excimeric states, which coexists with higher-energy fl uorescence. This can be exploited in light-emitting diodes, which show the same hybrid singlet and low-energy excimer electroluminescence. Low-voltage FETs are fabricated with epindolidione, which operate reliably under repeated cyclic tests in different ionic solutions within the pH range 3-10 without degradation. Finally, in order to overcome the insolubility of epindolidiones in organic solvents, a chemical procedure is devised to allow solution-processing via the introduction of suitable thermolabile solubilizing groups. This work shows the versatile potential of epindolidione pigments for electronics applications.

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Section: Crystal Structurementioning

confidence: 92%

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

Głowacki

Romanazzi

Yumusak

et al. 2014

Adv Funct Materials

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“…340,341 These pigments are synthesized from furfural and dialkylsuccinate ( Figure 26). Furfural is derived from biomass and is commercially available in large quantities at low cost.…”

Section: Low-cost Synthetic Semiconductorsmentioning

confidence: 99%

Sustainable Life Cycles of Natural-Precursor-Derived Nanocarbons

2015

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Sustainable societal and economic development relies on novel nanotechnologies that offer maximum efficiency at minimal environmental cost. Yet, it is very challenging to apply green chemistry approaches across the entire life cycle of nanotech products, from design and nanomaterial synthesis to utilization and disposal. Recently, novel, efficient methods based on nonequilibrium reactive plasma chemistries that minimize the process steps and dramatically reduce the use of expensive and hazardous reagents have been applied to low-cost natural and waste sources to produce value-added nanomaterials with a wide range of applications. This review discusses the distinctive effects of nonequilibrium reactive chemistries and how these effects can aid and advance the integration of sustainable chemistry into each stage of nanotech product life. Examples of the use of enabling plasma-based technologies in sustainable production and degradation of nanotech products are discussed-from selection of precursors derived from natural resources and their conversion into functional building units, to methods for green synthesis of useful naturally degradable carbon-based nanomaterials, to device operation and eventual disintegration into naturally degradable yet potentially reusable byproducts.

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“…Recently, many small pigment molecules with fused hydrogen‐bonding have been reported to exhibit high charge carrier mobilities. Although those pigment molecules contain carbonyl and amine groups that have been regarded as perturbation groups for π‐conjugation; the strong intermolecular hydrogen‐bonding can serve as crystallization driving force to assemble those pigment molecules into highly ordered structure, which eventually leads to narrowed bandgaps and efficient charge transport between molecules.…”

Section: Introductionmentioning

confidence: 99%

Polymers Based on Benzodipyrrolidone and Naphthodipyrrolidone with Latent Hydrogen‐Bonding on the Main Chain

Zhang

Yang

Chen

et al. 2017

Macro Chemistry & Physics

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A series of soluble π‐conjugated small molecules and polymers containing benzodipyrrolidone (BDP) or naphthodipyrrolidone (NDP) units with latent hydrogen‐bonding on the main chain is synthesized and characterized. Spectroscopic study confirms that the tert‐butyloxycarbonyl (t‐Boc) side unit can be removed by facile thermal annealing treatment, generating the actual hydrogen‐bonded compounds. The resulting hydrogen‐bonded compounds exhibit distinctly different properties, for instance poorer solubility and smaller bandgap, as compared with their precursors with latent hydrogen‐bonding. The single crystal X‐ray structure analysis of t‐Boc group substituted BDP and NDP indicates that the NDP compounds exhibit better coplanarity and a stronger π–π interaction. The density functional theory computation results of the polymer backbone segments show that the coplanarity of aromatic units is slightly improved. Such a hydrogen‐bonding‐mediated enhancement of π–π stacking exhibits potential for improving the performance of solution processable organic electronic materials. Hydrogen‐bonded polymer P‐NDP‐FL‐2 is an air stable n‐type semiconductor with electron mobility 40 times larger than its precursor polymer P‐NDP‐FL‐1 with latent hydrogen‐bonding.

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Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors

Abstract: Graphical abstract

Cited by 106 publications

References 41 publications

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

Sustainable Life Cycles of Natural-Precursor-Derived Nanocarbons

Polymers Based on Benzodipyrrolidone and Naphthodipyrrolidone with Latent Hydrogen‐Bonding on the Main Chain

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