Indigo ‐ A Natural Pigment for High Performance Ambipolar Organic Field Effect Transistors and Circuits

Irimia‐Vladu, Mihai; Głowacki, Eric Daniel; Troshin, Pavel A.; Schwabegger, Günther; Leonat, Lucia; Susarova, Diana K.; Krystal, Olga; Ullah, Mujeeb; Kanbur, Yasin; Bodea, M.A.; Разумов, В. Ф.; Sitter, H.; Bauer, Siegfried; Sariciftci, Niyazi Serdar

doi:10.1002/adma.201102619

Cited by 398 publications

(348 citation statements)

References 32 publications

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“…Chemical investigation and archaeological evidence have shown that purple was widely spread after the deposition of the body for burial. These results are the earliest chemical evidence of purple colorant used during funeral rituals (not as textile dye) and enabled us to highlight new aspects of funeral practices in Roman times [30] .…”

Section: Tyrian Purplementioning

confidence: 74%

“…During the past 30 years, a core group of marine natural products (MNPs) chemists from several countries, in collaboration with both academic pharmacologists and the pharmaceutical industry, have reported a very large number of novel metabolites with useful and sometimes sensational pharmacological properties. However, MNPs are exhibiting high antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

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RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

Kaviarasan

Siva

Yogamoorthi

2012

Asian Pacific Journal of Tropical Biomedicine

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Section: Tyrian Purplementioning

confidence: 74%

Section: Introductionmentioning

confidence: 99%

RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

Kaviarasan

Siva

Yogamoorthi

2012

Asian Pacific Journal of Tropical Biomedicine

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“…Indigo is a well-known natural dye used in blue jeans, and even this molecule itself shows ambipolar transport. 4 Isoindigo is an isomer with the same molecular formula, and copolymers with fluorene or benzothiadiazole show ambipolar characteristics with the mobilities exceeding 0.1 cm 2 V ¹1 s …”

mentioning

confidence: 99%

Estimated Mobility of Ambipolar Organic Semiconductors, Indigo and Diketopyrrolopyrrole

Kojima

Mori

2012

Chemistry Letters

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The title organic molecules, recently used as building blocks of ambipolar ³-conjugated polymers, are investigated by molecular orbital calculations. The tendency that the transfer integral and the reorganization energy increase at the same time helps the accomplishment of balanced hole and electron mobilities.Recently ambipolar organic semiconductors exhibiting both hole and electron transport have attracted considerable attention on account of the applications to organic photovoltaics and lightemitting transistors.1 Since organic semiconductors are intrinsic semiconductors in general, it is important for hole and electron injection that HOMO and LUMO levels match the work functions of metal electrodes. Thus the narrow energy gap is requisite to realize an ambipolar transport.2 In addition, high mobilities for carriers with both signs are necessary. Conjugated polymers consisting of electronic donating and deficient groups fulfill these points and are widely investigated as ambipolar semiconductors.3 In this connection, organic dyes and pigments have been investigated as building blocks of donoracceptor polymers (Chart 1). These units are electron deficient and have comparatively narrow energy gaps. Indigo is a well-known natural dye used in blue jeans, and even this molecule itself shows ambipolar transport. 4 Isoindigo is an isomer with the same molecular formula, and copolymers with fluorene or benzothiadiazole show ambipolar characteristics with the mobilities exceeding 0.1 cm 2 V ¹1 s ¹1. 5,6 Diketopyrrolopyrrole (DPP, Chart 1) is one of the most intensively studied building blocks in ambipolar polymers, where several polymeric materials have been reported to achieve very high mobility exceeding 1 cm 2 V ¹1 s ¹1 . 7 The monomeric trifluoromethylated DPP derivative also exhibits ambipolar behavior. 8 In this letter, we investigate the molecular orbitals of these organic dyes and pigments.Since the carrier transport in organic transistors is usually governed by the multiple trapping-and-release mechanism, 9 the hole and electron mobilities (®) were calculated on the basis of the Marcus theory, 10,22andwhere r i is an intermolecular distance and P i is the relative probability of charge transport. The hopping rate (k) is calculated for each transport pathway. In the present study, the transfer integrals (t) were evaluated from the overlap of the molecular orbitals between the neighboring molecules based on the extended Hückel orbitals. 11 The reorganization energy () is a sum of the structural relaxation energies accompanied by the process from the neutral to the charged state and that of the inverse process.12 Accordingly, small affords large ®. In the present paper, was calculated from the molecular orbital calculations by using Gaussian 09 at B3LYP/6-31G(d,p) level. 13Indigo has two kinds of crystal structures, which will be called phase I (ref. 14) and II (ref. 15) in this paper, where phase I has a smaller cell volume. Both phases belong to the same space group and have similar one-dimensional stackin...

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“…Hole and electron mobility of 0.01 cm 2 V ¹1 s ¹1 has been observed in indigo, 103 which is a dye used in blue jeans, and the characteristic deep blue color comes from the small HOMO LUMO gap of 1.7 eV. We have improved the ambipolar operation to 0.56/0.95 cm 2 V ¹1 s ¹1 and 0.42/0.85 cm 2 V ¹1 s ¹1 , respectively in diphenyl and diiodo-indigo.…”

mentioning

confidence: 99%

“…101 Recently, high-performance ambipolar transistors have been realized using donor-acceptor polymers. 102 Among small molecules, stable ambipolar transistors have been achieved using a passivation layer of tetratetracontane (TTC, C 44 H 90 ), 103,104 where even pentacene shows ambipolar characteristics. 105 The operation regions of an ambipolar transistor are divided as shown in Figure 16 depending on the polarity of the gate voltage V G and the drain voltage V D , 106 where it is important to consider nonzero electron and hole threshold voltages, V T and V T ¤.…”

mentioning

confidence: 99%

Principles that Govern Electronic Transport in Organic Conductors and Transistors

Mori¹

2016

Bulletin of the Chemical Society of Japan

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Energy bands of organic conductors are calculated on the basis of the estimation of intermolecular overlap integrals and the tight-binding approximation. The resulting Fermi surface has been investigated by the measurements of low-temperature magnetoresistance in detail. However, we have to take electron correlation into account to explain the variation of the metal-insulator transition temperatures and the universal phase diagram. In particular, intermolecular Coulomb repulsion gives a variety of charge-order patterns, in which non-stripe charge order is important in a triangular network of organic conductors. Non-stripe charge order is an origin of flat resistivity, nonlinear conductivity, and potentially Dirac fermions. The estimation of intermolecular interaction is extended to the πd-systems, where the magnetic interactions J between the π-electrons and metal spins make a network. To discuss the charge transport in organic transistors, energy levels of the molecules are important. However, since the energy levels are considerably modified at the metal/organic interface, it is useful to use chemical doping and organic charge-transfer salts in the conducting parts of organic transistors. Temperature dependence of an organic transistor comes from the midgap trap states, but eliminating the traps in a single-crystal transistor, we can achieve band-like transport maintained down to low temperatures.

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Indigo ‐ A Natural Pigment for High Performance Ambipolar Organic Field Effect Transistors and Circuits

Cited by 398 publications

References 32 publications

RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

Estimated Mobility of Ambipolar Organic Semiconductors, Indigo and Diketopyrrolopyrrole

Principles that Govern Electronic Transport in Organic Conductors and Transistors

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