Supramolecular Structures and Assembly and Luminescent Properties of Quinacridone Derivatives

Ye, Kaiqi; Wang, Jia; Sun, Hui; Liu, Yu; Mu, Zhongfei; Li, Fēi; Jiang, Shimei; Zhang, Jingying; Zhang, Hongxing; Wang, Yue; Che, Chi‐Ming

doi:10.1021/jp0444767

Cited by 137 publications

(138 citation statements)

References 26 publications

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“…Here, the slight improved EL performance of Ir2 compared to Ir1 indicates that the methyl substituent could partly suppress the aggregation of the emitting core in the solid thin films, and thereby favour enhanced device EL efficiency. 18 To the best of our knowledge, these EL efficiencies strongly compete with, and even exceed, any previously reported values for deep-blue PhOLEDs with similar CIE x,y values.…”

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confidence: 75%

Rational design and characterization of heteroleptic phosphorescent iridium(iii) complexes for highly efficient deep-blue OLEDs

et al. 2016

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supporting

confidence: 75%

Rational design and characterization of heteroleptic phosphorescent iridium(iii) complexes for highly efficient deep-blue OLEDs

et al. 2016

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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]. 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.…”

mentioning

confidence: 99%

“…Previous work showed the assembly of long-chain molecules including QAnC on solid-liquid interfaces and a highly oriented pyrolytic graphite surface [12,13,15,16], in which the molecule-substrate interaction is normally the non-site-specific pi-pi interactions and the structures were arranged by relative weak intermolecular interactions at solid-liquid interface. However, from the viewpoint of modeling the growth, noble metal substrates are much more attractive and versatile.…”

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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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“…,10-tetramethylquinacridone (C10TMQA), were synthesized according to the published procedure [28,34]. The solution evaporation method was used to fabricate the samples.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, some highly anisotropic achiral molecules such as amphiphilic cyanine dyes, cationic surfactants, and asymmetric porphyrins, have been used to prepare twisted or helical nano-structures [15 20]. The design and synthesis of achiral organic functional molecules which can assemble into well-defined twisted or helical architectures in the 3,8,, were synthesized according to the published procedure [28,34]. The solution evaporation method was used to fabricate the samples.…”

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Self-assembly of luminescent twisted fibers based on achiral quinacridone derivatives

Zhao

Fan

et al. 2009

Nano Res.

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It is a great challenge to spontaneously assemble achiral molecules into twisted nanostructures in the absence of chiral substances. Here we show that two achiral centrosymmetric quinacridone (QA) derivatives, N,N'-di(n-hexyl)-1, 3, 8,3, 8,, can be employed as building blocks to fabricate well-defi ned twisted nanostructures by controlling the solvent composition and concentration. Bowknot-like bundles with twisted fiber arms were prepared from C6TMQA, whilst uniform twisted fibers were generated from C10TMQA in ethanol/THF solution. Spectroscopic characterization and molecular simulation calculations revealed that the introduction of ethanol into the solution could induce a staggered aggregation of C6TMQA (or C10TMQA) molecules and the formation of twisted nanostructures. Such twisted materials generated from achiral organic functional molecules may be valuable in the design and fabrication of new materials for optoelectronic applications. KEYWORDSTwisted fi ber, quinacridone, self-assembly, luminescenceThe self-assembly of twisted or helical nanostructures based on functional organic molecules has become a hot topic. The construction of these nano-structures is very important in increasing our understanding of some life substances and may afford a promising approach toward the design and synthesis of materials with potential applications in areas such as sensors, liquid crystals, and optical activity [1 6]. Three strategies have been employed to construct helical or twisted structures. Generally, the supramolecular helical or twisted objects have been generated by assembling small organic molecules containing chiral groups such as peptides, lipid bilayers, glucose, bola-amphiphiles, or π-conjugant oligomers [7 12]. In some cases, achiral molecules can be assembled into twisted or helical fibers through the introduction of chiral molecule templates [13, 14]. Furthermore, some highly anisotropic achiral molecules such as amphiphilic cyanine dyes, cationic surfactants, and asymmetric porphyrins, have been used to prepare twisted or helical nano-structures [15 20]. The design and synthesis of achiral organic functional molecules which can assemble into well-defined twisted or helical architectures in the 3,8,, were synthesized according to the published procedure [28,34]. The solution evaporation method was used to fabricate the samples. A 50 μL aliquot of C6TMQA or C10TMQA in ethanol/THF (THF = tetrahydrofuran) solution was dropped on a substrate located in a glass container with a cover. After natural evaporation of the solvents at room temperature, the samples were generated on the substrate. Nano Researchwhen the molar ratio of ethanol/C6TMQA (R C6 ) was in the range 1000 to 12,000. Fluorescence microscopy and field emission scanning electron microscopy (FESEM) revealed that the bowknot-like bundles were formed from twisted fibers (Figs. 1(a) (c)). The arm diameters of the bowknots were about 200 nm with lengths of up to several micrometers. For a given concentration of C6TMQA, the R C6 value is crit...

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Supramolecular Structures and Assembly and Luminescent Properties of Quinacridone Derivatives

Cited by 137 publications

References 26 publications

Rational design and characterization of heteroleptic phosphorescent iridium(iii) complexes for highly efficient deep-blue OLEDs

Rational design and characterization of heteroleptic phosphorescent iridium(iii) complexes for highly efficient deep-blue OLEDs

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

Self-assembly of luminescent twisted fibers based on achiral quinacridone derivatives

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