Supramolecular architecture and electrical conductivity in organic semiconducting thin films

Fernandes, José Diego; Maximino, Mateus D.; Braunger, Maria Luisa; Pereira, Matheus S.; Olivati, Clarissa de Almeida; Constantino, Carlos J. L.; Aléssio, Priscila

doi:10.1039/d0cp01293a

Cited by 10 publications

(7 citation statements)

References 52 publications

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“…The reaction mixture was refluxed under dry atmosphere for about 6 h. Then it was slowly cooled to room temperature to obtain a yellow crystalline solid of compound 1. The structure of the compound 1 has been confirmed by, mass spectrometry, 1 H and 13 C NMR, IR and electronic spectroscopy.…”

Section: Synthesis Of Compoundmentioning

confidence: 83%

“…The 1 H NMR spectra of the compound 1 in CDCl3 showed a singlet at δ 7.80 ppm due to HC=N proton, other aryl protons resonates in between δ 9.16 to 7.47 ppm. In the 13 C NMR spectra the -C=N carbon appears at δ 166.53 ppm and the other aryl carbons resonate between δ 157.50 to 127.48 ppm (expected region). Compound 1 crystallizes in the triclinic space group P-1 and the asymmetric unit contains a single molecule of compound 1 (Scheme 1).…”

Section: Synthesis and Structurementioning

confidence: 99%

“…hydrogen bonding, ionic interactions and π-π stacking interactions have fascinated increasing attention in crystal engineering. In particular, hydrogen bonding π-π stacking interactions which is a powerful organizing force in designing various supramolecular and solid-state architectures [8][9][10], is extensively used not only for networking numerous organic and organometallic compounds [11,12], but also for generating interesting supramolecular properties, such as electrical, optical and magnetic [13,14] properties. Quinoline groups, with effective sites for coordination to transition metal ions, have been used for the construction of supramolecular coordination compounds [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone

Patra

Manna

2021

Eur J Chem

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The synthesis, characterization, and theoretical studies of a novel hydrazine, N,N’-bis-(3-quinolylmethylene)diphenylethanedione dihydrazone (1) has been reported. The molecular structure has been characterized by room-temperature single-crystal X-ray diffraction which reveals that two quinoline moieties are disposed nearly perpendicularly around the central C-C bond giving a ‘L’ shape of the molecule. This particular geometry gives rise to the hydrogen-bonded supramolecular rectangle of two self-complementary molecules. These supramolecular units are further assembled by π-π interaction. The Hirshfeld surface analysis of compound 1 shows that C···C, C···H, H···H, and N···H interactions of 13.1, 9.9, 52.3, and 7.4%, respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. Crystal data for C34H24N6: Triclinic, space group P-1 (no. 2), a = 10.885(3) Å, b = 11.134(3) Å, c = 12.870(3) Å, α = 90.122(6)°, β = 114.141(6)°, γ = 110.277(5)°, V = 1316.1(6) Å3, Z = 2, T = 100(2) K, μ(MoKα) = 0.080 mm-1, Dcalc = 1.304 g/cm3, 7309 reflections measured (3.518° ≤ 2Θ ≤ 39.276°), 2318 unique (Rint = 0.0527, Rsigma = 0.0565) which were used in all calculations. The final R1 was 0.0416 (I > 2σ(I)) and wR2 was 0.1074 (all data).

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Section: Synthesis Of Compoundmentioning

confidence: 83%

Section: Synthesis and Structurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone

Patra

Manna

2021

Eur J Chem

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“…The diluted perylene solutions down to 10 –6 mol L –1 were prepared only in DCM solvent (10 –3 mol L –1 ). This 10 –3 mol L –1 is a typical concentration reported in the literature , for such molecules with surface activity; therefore, it was an optimization of the Langmuir film experiment. Perylene derivatives are found in the monomeric phase in concentrations less than 10 –6 mol L –1 and in some cases from 10 –9 mol L –1 , , which would make it difficult to carry out LS film experiments.…”

Section: Methodsmentioning

confidence: 99%

Langmuir–Schaefer Perylene Derivative Films: Influence of the Molecular Chemical Structure on the Supramolecular Arrangement

et al. 2021

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Since the optical and electrical properties of organic thin films devices depend on their supramolecular arrangement and the molecular chemical structure, the understanding of such characteristics is essential for the optimization of these devices. In this study, we determine the supramolecular arrangement of thin films produced using the Langmuir–Schaefer (LS) technique and explain how its supramolecular arrangement is affected by the molecular chemical structure using two perylene derivatives: bis-butylimide (BuPTCD) and bis-phenethylimide (PhPTCD). The optical absorption measurements reveal that both films grow homogeneously and indicate that the presence of H aggregates (forbidden emission) is higher for BuPTCD LS film than for PhPTCD LS film. Atomic force microscopic analysis shows that the PhPTCD LS film is rougher than the BuPTCD film. In addition, FTIR analyses indicate that both films have head-on molecular organization. XRD patterns reveal that both the BuPTCD LS film and the PhPTCD LS film are crystalline, but that crystallinity is more prevalent in the BuPTCD LS film. Thus, the results show that the difference presented in the chemical structures leads the films to have different supramolecular arrangements, with consequences for their optical properties.

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“…In addition to the typical amphiphilic molecules described above, the LB technique is largely enlarged towards the assembly of more complex structures with interest in molecular electronics (and organic electronics). Polymers [281][282][283], metalloporphyrines [284], DNA [285], perylenes [286], perylene-NH 2 [287], ruthenium complexes [288], organo-modified inorganic nanoparticles in combination with polymer nanospheres (nano-mille-feuille system) [289], pillar [5]arene derivatives [290], polymer-coated CsPbBr 3 nanowires [291], aligned SWCNTs [145], semi-conductive 2D materials based on 2,3,6,7,10,11-hexaiminotriphenylene (HATP) [292], or rGO [146] have been used.…”

Section: The Langmuir-blodgett Techniquementioning

confidence: 99%

Nanofabrication Techniques in Large-Area Molecular Electronic Devices

2020

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The societal impact of the electronics industry is enormous—not to mention how this industry impinges on the global economy. The foreseen limits of the current technology—technical, economic, and sustainability issues—open the door to the search for successor technologies. In this context, molecular electronics has emerged as a promising candidate that, at least in the short-term, will not likely replace our silicon-based electronics, but improve its performance through a nascent hybrid technology. Such technology will take advantage of both the small dimensions of the molecules and new functionalities resulting from the quantum effects that govern the properties at the molecular scale. An optimization of interface engineering and integration of molecules to form densely integrated individually addressable arrays of molecules are two crucial aspects in the molecular electronics field. These challenges should be met to establish the bridge between organic functional materials and hard electronics required for the incorporation of such hybrid technology in the market. In this review, the most advanced methods for fabricating large-area molecular electronic devices are presented, highlighting their advantages and limitations. Special emphasis is focused on bottom-up methodologies for the fabrication of well-ordered and tightly-packed monolayers onto the bottom electrode, followed by a description of the top-contact deposition methods so far used.

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Supramolecular architecture and electrical conductivity in organic semiconducting thin films

Abstract: Organic thin films supramolecular architecture plays an essential factor in the performance of optical and electronic organic devices.

Cited by 10 publications

References 52 publications

Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone

Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone

Langmuir–Schaefer Perylene Derivative Films: Influence of the Molecular Chemical Structure on the Supramolecular Arrangement

Nanofabrication Techniques in Large-Area Molecular Electronic Devices

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