Cation-induced self-assembly of an amphiphilic perylene diimide derivative in solution and Langmuir–Blodgett films

Zou, Lei; You, Ao; Song, Jingang; Li, Xingzhen; Bouvet, Marcel; Sui, Weiping; Chen, Yanli

doi:10.1016/j.colsurfa.2014.10.021

Cited by 13 publications

(8 citation statements)

References 51 publications

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“…This distance is assigned to the distance between two adjacent 1 molecules in the longitudinal direction. 66 Considering the dimensions of the present molecule as 1.739 nm × 0.8 nm × 0.34 nm, the observed distance is consistent with the typical distance for effective π−π stacking between the aromatic molecules. This suggests that molecule 1 remained flat horizontally in the multilayer.…”

Section: ■ Discussionsupporting

confidence: 80%

“…A similar feature in the XRD spectra for other imidazole derivatives has also been reported. , The calculated layer distance was found to be on the order of 0.4 nm corresponding to 2θ = 22.03° using Bragg’s equation. This distance is assigned to the distance between two adjacent 1 molecules in the longitudinal direction . Considering the dimensions of the present molecule as 1.739 nm × 0.8 nm × 0.34 nm, the observed distance is consistent with the typical distance for effective π–π stacking between the aromatic molecules.…”

Section: Discussionsupporting

confidence: 72%

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Study of Compression-Induced Supramolecular Nanostructures of an Imidazole Derivative by Langmuir–Blodgett Technique

Dey¹,

Debnath²,

Chakraborty

et al. 2017

Langmuir

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In this communication, we report the design and synthesis as well as the supramolecular assembly behavior of a 2,4,5-triaryl imidazole derivative (compound 1) at the air-water interface and in thin films using Langmuir-Blodgett (LB) technique. The main idea for such a chemical structure is that the long alkyl chain and N-H of the imidazole core may help to form supramolecular architecture through the hydrophobic-hydrophobic interaction and hydrogen bonding, respectively. Accordingly, the interfacial behavior as well as morphology of 1 in thin films were studied through a series of characterization methods such as surface pressure-area (π-A) isotherm, hysteresis analysis, ultraviolet-visible (UV-vis) absorption and steady-state fluorescence spectroscopies, Fourier transform infrared, X-ray diffraction, Brewster angle microscopy (BAM), and atomic force microscopy (AFM) measurements, and so forth. Pressure-area isotherm is an indication toward the formation of supramolecular nanostructures instead of an ideal monolayer at the air-water interface. This has been confirmed by the hysteresis analysis and BAM measurement at the air-water interface. AFM images of 1 in the LB monolayer exhibits the formation of supramolecular nanowires as well as nanorods. By controlling different film-forming parameters, it becomes possible to manipulate these nanostructures. With the passage of time, the nanowires come close to each other and become straight. Similarly, nanorods come close to each other and form bundles of several rods in the LB films. H-bonding, J-aggregation, as well as compression during film formation might play a key role in the formation of such nanostructures. Electrical switching behavior of compound 1 was also observed because of the presence of an electron donor-acceptor system in 1. This type of organic switching behavior may be promising for next-generation organic electronics.

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Section: ■ Discussionsupporting

confidence: 80%

Section: Discussionsupporting

confidence: 72%

Study of Compression-Induced Supramolecular Nanostructures of an Imidazole Derivative by Langmuir–Blodgett Technique

Dey¹,

Debnath²,

Chakraborty

et al. 2017

Langmuir

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“…Moreover, PTCDIs assembly could be tested from the absorption spectra at long wavelength ranges as seen in SI Figure S5. One major explanation is that the H-type aggregations of PTCDIs decrease the intensity of characteristic absorption peaks of 0 → 1 and 0 → 0 vibronic bands. , In addition, with the end of self-assembly for PTCDIs, the accompanying reduction of fluorescence intensity could be explained by the effect of aggregation-caused quenching (ACQ).…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Study of Structure Tunable Perylene Diimides and The Nanofibers Deposited on Electrodes

Xue

Chen

et al. 2019

Langmuir

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The electrochemical behavior of organic conjugated semiconductors and their bulk materials is a considerable and irreplaceable parameter to maintain their diverse electronic or optoelectronic applications. In this paper, a series of n-type symmetrical perylene diimide derivatives (PTCDIs) with substituents (3,4-ethylenedioxythiophene (EDOT), cyclohexane, acetic acid, or propionic acid) at located the nitrogens imide position were synthesized, and their solubility, optical features, thermal stability, as well as solution-phase interfacial selfassembly into one-dimensional (1D) nanofibers and related morphology were discussed in detail. Moreover, a simple but effective method, in situ deposition following in situ self-assembly, was developed to construct uniform electrodes over a large area coated with networked PTCDI nanofibers. Then the electrochemical properties of the PTCDI nanofibers were researched in comparison with their molecules. The excellent variability at molecular or nanoscale morphological level will provide an interesting insight into the research of PTCDIs in a wide range applications of organic electronics.

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“…Thus, reorientation is essentially hampered, and the dyes form J aggregates upon lateral compression of the Langmuir layer. The joint stabilization of this NiBi layer by π–π and dipolar interactions gives rise to considerably high surface pressures of ≈45 mN/m, ,,,− which are obtained without any signs of disturbance of the monolayer.…”

Section: Discussionmentioning

confidence: 99%

Assembly of T-Shaped Amphiphilic Thiazoles on the Air–Water Interface: Impact of Polar Chromophore Moieties, as Well as Dipolarity and π-Extension of the Chromophore on the Supramolecular Structure

et al. 2019

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The supramolecular structure essentially determines the properties of organic thin films. In this work, we systematically investigate the influence of the chromophore on the supramolecular structure formation at air–water interfaces by means of the Langmuir–Blodgett technique. Therefore, we focus on the recently introduced class of double-anchor T-shaped amphiphilic dyes, namely, 4-hydroxy-thiazole chromophores that are centrally equipped with an amphiphilicity-inducing hexanoic acid. The thiazoles contain hydrophilic subphase-anchor groups in the 2-position (4-N,N-dimethylaminophenyl (Am), 2-pyridyl (Py), and 4-nitrophenyl (Ni)), whereas the chromophores are systematically extended in the 5-position with various substituents. The combination of the Langmuir technique with online fluorescence measurements revealed that the π–π interactions that are pronounced in the case of 4-methoxybiphenyl derivatives yield the most distinct supramolecular structures. Whereas in the case of Py and Ni derivatives ordered J-type supramolecular structures in microdomains are formed, the Am derivative forms ordered supramolecular structures that are more homogeneous, which are, however, not stabilized by J-type dipolar interactions. Because of the synergetic π–π and dipolar stabilizations, the Ni derivative bearing the 4-methoxybiphenyl unit forms exceptionally stable quasi-two-dimensional Langmuir monolayers reaching very high surface pressures beyond 60 mN/m without any sign of disturbance of the Langmuir monolayer.

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Cation-induced self-assembly of an amphiphilic perylene diimide derivative in solution and Langmuir–Blodgett films

Cited by 13 publications

References 51 publications

Study of Compression-Induced Supramolecular Nanostructures of an Imidazole Derivative by Langmuir–Blodgett Technique

Study of Compression-Induced Supramolecular Nanostructures of an Imidazole Derivative by Langmuir–Blodgett Technique

Electrochemical Study of Structure Tunable Perylene Diimides and The Nanofibers Deposited on Electrodes

Assembly of T-Shaped Amphiphilic Thiazoles on the Air–Water Interface: Impact of Polar Chromophore Moieties, as Well as Dipolarity and π-Extension of the Chromophore on the Supramolecular Structure

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