Orientation Control of Quinacridone Derivatives with Long Alkyl Chains in Langmuir-Blodgett Films

Nakahara, Hiroyuki; Kitahara, Kiyoshi; Nishi, Hisao; Fukuda, Kiyoshige

doi:10.1246/cl.1992.711

Cited by 28 publications

(34 citation statements)

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“…Such aggregation is observed for quinacridone (QA) and its derivatives, which are widely used as organic pigments that display excellent fastness as well as pronounced photovoltaic and photoconducting activity. [27,28] We used N, N′-di(n-butyl)quinacridone (DBQA), a derivative of QA, in this work (Fig. 1a).…”

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confidence: 99%

Multicolor Emission on Prepatterned Substrates Using a Single Dye Species

Lü

Zhang

et al. 2007

Advanced Materials

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A new strategy for realizing patterned surfaces with different emission colors is demonstrated. This approach relies on the gas‐phase deposition of dye molecules onto solid substrates that are prepatterned by nanoimprint lithography (see figure). Only a single molecular species is involved. Thus, the observed color change and corresponding spectral shift in the emission properties depends on the substrate used and can be tuned by surface engineering.

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confidence: 99%

Multicolor Emission on Prepatterned Substrates Using a Single Dye Species

Lü

Zhang

et al. 2007

Advanced Materials

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“…They display excellent photovoltaic and photoconductive properties [8][9][10]. The performance of organic light emitting devices based on QA have been widely investigated [11][12][13][14].…”

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confidence: 99%

Role of Lateral Alkyl Chains in Modulation of Molecular Structures on Metal Surfaces

et al. 2006

Phys. Rev. Lett.

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We use low energy electron diffraction, scanning tunneling microscopy, first-principles densityfunctional theory, and molecular mechanics calculations to analyze the adsorption and growth of quinacridone derivatives (QA) with alkyl chains of 4 and 16 carbon atoms on a Ag(110) substrate. Surprisingly, we find that the alkyl chains determine the orientation of the molecular overlayers. While the interaction of QA and the Ag substrate is primarily due to chemical bonding of oxygen to the silver substrate, determining the molecular orientation and preferred adsorption site, the intermolecular arrangement can be adjusted via the length of alkyl chains. We are thus able to fabricate uniform QA films with very well controlled physical properties. DOI: 10.1103/PhysRevLett.96.226101 PACS numbers: 81.07.Nb, 68.43.ÿh, 81.16.Dn In recent years, the structure and growth of functional molecular thin films have been widely investigated due to their potential application for molecular devices [1][2][3][4]. However, understanding the interactions between organic molecules and noble metal substrates is not straightforward and has proven to be rather challenging [1][2][3][4][5]. In this respect, the ability to control the structure of molecular thin films provides a method of tuning the functional properties in a discrete manner. Previous work demonstrated that linear aromatic hydrocarbons attach to a silver substrate via interactions of the lowest unoccupied molecular orbital (LUMO) and silver 4d orbitals [6]. The match of the LUMO and the silver 4d orbitals also dominates the structural properties of the ensuing molecular film. Subsequent work concerned the lateral functional groups interacting with silver substrates, such as CN and CO groups in DMe-DCNQI and PTCDA [7]. The work suggested that the adsorbate-substrate geometry of large aromatic molecules on noble metal surfaces can be precisely controlled by functional groups of the molecule. However, the intermolecular geometry is less well researched due to lack of experimental data. Correspondingly, the understanding of intermolecular interaction is still somewhat shallow.For example, quinacridone and its derivatives (QA) are well-known chemically stable pigments. They display excellent photovoltaic and photoconductive properties [8][9][10]. The performance of organic light emitting devices based on QA have been widely investigated [11][12][13][14]. The QA molecular structure can be varied by the substitution of C atoms by N and O. QA can also be modified by attaching lateral alkyl chains to N heteroatoms and by the formation of QAnC, as shown in Fig. 1(a), where n denotes the number of carbon atoms in each alkyl chain. Accordingly, the photoelectric or electrical property can be adjusted by structural alterations of the molecule. It is quite possible that the lateral alkyl chains act as spacers and modulate the intermolecular distance. In this case the energy transfer between QAnC functional units is modified by noncovalent interactions between molecules, which are tuned ...

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“…Quinacridone (QA) and its derivatives are widely used organic pigments that display pronounced photovoltaic and photoconductive activities [1][2][3][4][5][6]. In addition, the excellent self-assembly properties as well as the importance as emitting materials in organic light-emitting diodes (OLEDs) have added to the intensity of research on this class of pigments.…”

Section: Introductionmentioning

confidence: 99%

“…Müllen and co-workers have carefully studied the phase-formation behavior and aggregation properties of some soluble QA derivatives [7,8]. Nakahara and coworkers have synthesized QA derivatives with alkyl chains and used them in Langmuir-Blodgett films to control the orientation and packing of the chromophores [3,4]. High luminescent efficiencies in dilute solutions combined with good electrochemical stabilities in the solid states enable QA dyes to be promising guest emitting materials in OLEDs [9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Dimeric quinacridone cyclophanes: Synthesis, structures, and photophysical properties

Peng

Iqbal

et al. 2011

Sci. China Chem.

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Two novel quinacridone (QA) cyclophanes with intrinsic intramolecular dye-dye interactions have been designed and synthesized. X-ray crystal structures as well as detailed photophysical properties have been well demonstrated. These two dyes have a major advantage that efficient fluorescence quenching can be observed even in their dilute solutions. A comparison of photophysical properties between the dimeric QA cyclophane and its reference monomeric counterpart indicates that the dimerization is predominant for the fluorescence quenching of QA dyes in solution. This study provided some model QA derivatives with dimeric structures for understanding the fluorescence quenching of QA dyes in solutions. quinacridone, cyclophanes, dye-dye interactions, photophysics, fluorescence quenching

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Orientation Control of Quinacridone Derivatives with Long Alkyl Chains in Langmuir-Blodgett Films

Cited by 28 publications

References 1 publication

Multicolor Emission on Prepatterned Substrates Using a Single Dye Species

Multicolor Emission on Prepatterned Substrates Using a Single Dye Species

Role of Lateral Alkyl Chains in Modulation of Molecular Structures on Metal Surfaces

Dimeric quinacridone cyclophanes: Synthesis, structures, and photophysical properties

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