A new crystalline phase of indigo

Süsse, P.; Wolf, Andreas

doi:10.1007/bf00405640

Cited by 33 publications

(24 citation statements)

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“…That is, the intermolecular Η-bond bridges the two different stacking columns in such a way that one molecule is hydrogen-bonded to two neighboring molecules. The present molecular arrangement is basically quite similar to the one observed for the γ phase of unsubstituted quinacridone [5,7] and also indigos [8,9]. …”

supporting

confidence: 82%

Crystal structure of 5,12-dihydro-5-methylquino[2,3-b]acridine-7,14-dione, C21H14N2O2, at 93 Κ

Mizuguchi¹,

Senju²

2002

Zeitschrift Für Kristallographie - New Crystal Structures

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to cancel the dipole moment to stabilize themselves electrostatically. There are chains of intermolecular hydrogen bonds between the NH group of one molecule in the one column and the O atom of another molecule in the neighboring column. That is, the intermolecular Η-bond bridges the two different stacking columns in such a way that one molecule is hydrogen-bonded to two neighboring molecules. The present molecular arrangement is basically quite similar to the one observed for the γ phase of unsubstituted quinacridone [5,7] and also indigos [8,9].

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supporting

confidence: 82%

Crystal structure of 5,12-dihydro-5-methylquino[2,3-b]acridine-7,14-dione, C21H14N2O2, at 93 Κ

Mizuguchi¹,

Senju²

2002

Zeitschrift Für Kristallographie - New Crystal Structures

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“…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 stacking structures along the b axis ( Figure 1a).…”

mentioning

confidence: 73%

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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“…However, the molecules are not entirely on the molecular plane, (3) Â. The present Η-bond network is strikingly different from that of the y phase of unsubstituted quinacridone [16,17], dithioquinacridone [18] and also indigos [19,20], in which one molecule is bonded to four different neighboring molecules as characterized by a three-dimensional Η-bond network. …”

Section: Discussionmentioning

confidence: 73%

Crystal structure of 5,12-dihydro-2,9-dimethylquino[2,3-b]acridine-7,14- dione, C22H16N2O2, at 123 Κ

Mizuguchi¹,

Senju²,

Sakai³

2002

Zeitschrift Für Kristallographie - New Crystal Structures

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A new crystalline phase of indigo

Cited by 33 publications

References 0 publications

Crystal structure of 5,12-dihydro-5-methylquino[2,3-b]acridine-7,14-dione, C21H14N2O2, at 93 Κ

Crystal structure of 5,12-dihydro-5-methylquino[2,3-b]acridine-7,14-dione, C21H14N2O2, at 93 Κ

Estimated Mobility of Ambipolar Organic Semiconductors, Indigo and Diketopyrrolopyrrole

Crystal structure of 5,12-dihydro-2,9-dimethylquino[2,3-b]acridine-7,14- dione, C22H16N2O2, at 123 Κ

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