Electronic structure and charge-transport properties of symmetric linear condensed bis-benzothiadiazole derivatives

Cagardová, Denisa; Michalík, Martin; Poliak, Peter; Lukeš, Vladimı́r

doi:10.1016/j.molstruc.2018.07.093

Cited by 7 publications

(6 citation statements)

References 50 publications

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“…The group of V. Lukeš focused its attention on theoretically designed π−conjugated cores to find which ones are the best candidates to synthetize new compounds with improved properties for applications in optoelectronic devices [ 183 , 184 ]. In one work [ 183 ], they considered a series of 43 derivatives of the heterocyclic circulenes, called Sulflowers if the heteroatoms are sulfur atoms, or Selflowers if selenium atoms are present.…”

Section: Recent Advances In the Study Of Discotic Liquid Crystalsmentioning

confidence: 99%

Charge Mobility in Discotic Liquid Crystals

Termine

Golemme

2021

IJMS

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Discotic (disk-shaped) molecules or molecular aggregates may form, within a certain temperature range, partially ordered phases, known as discotic liquid crystals, which have been extensively studied in the recent past. On the one hand, this interest was prompted by the fact that they represent models for testing energy and charge transport theories in organic materials. However, their long-range self-assembling properties, potential low cost, ease of processability with a variety of solvents and the relative ease of tailoring their properties via chemical synthesis, drove the attention of researchers also towards the exploitation of their semiconducting properties in organic electronic devices. This review covers recent research on the charge transport properties of discotic mesophases, starting with an introduction to their phase structure, followed by an overview of the models used to describe charge mobility in organic substances in general and in these systems in particular, and by the description of the techniques most commonly used to measure their charge mobility. The reader already familiar or not interested in such details can easily skip these sections and refer to the core section of this work, focusing on the most recent and significant results regarding charge mobility in discotic liquid crystals.

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Section: Recent Advances In the Study Of Discotic Liquid Crystalsmentioning

confidence: 99%

Charge Mobility in Discotic Liquid Crystals

Termine

Golemme

2021

IJMS

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“…There is an unceasing interest in the investigation of Ox-Red and photophysical properties of 2,1,3-benzothiadiazoles (btd), bound with their specific intra/intermolecular interactions, electronic structure, and charge transfer processes. − Being good chromophores and fluorophores, btd derivatives are promising for several applications, such as the construction of organic light-emitting diodes, , fluorescent markers for mapping in living systems, − low band gap polymers for photovoltaics, , and photocatalysts and luminescent ligands for metal complexes. , Due to the special interest in the btd derivatives, their organic chemistry has been intensively studied. Numerous examples include 4,7-aryl-, , thiophene-, and fused bis-benzothiadiazole derivatives, pyridines, pyridazines, carbazoles, , and fluorinated compounds, as well as their methoxy- and dimethylamine derivatives …”

Section: Introductionmentioning

confidence: 99%

“…14,15 Due to the special interest in the btd derivatives, their organic chemistry has been intensively studied. Numerous examples include 4,7-aryl-, 16,17 thiophene-, 18 and fused bis-benzothiadiazole 19 derivatives, pyridines, 20 pyridazines, 21 carbazoles, 22,23 and fluorinated compounds, 24 as well as their methoxy-and dimethylamine derivatives. 25 Meanwhile, the chemistry of phosphazanes and their complexes is actively being studied; 26 they are promising compounds for the preparation of modern functional materials.…”

Section: ■ Introductionmentioning

confidence: 99%

Tuning of the Coordination and Emission Properties of 4-Amino-2,1,3-Benzothiadiazole by Introduction of Diphenylphosphine Group

Sukhikh

Khisamov

Баширов

et al. 2020

Crystal Growth & Design

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A novel amino-benzothiadiazole bearing diphenylphosphine groups (L) was designed and synthesized. A number of its coordination compounds of Cu(I) (1•0.75C 7 H 8 , 2a,b), Pd(II) (4), and Pt(II) (5) were prepared demonstrating the coordination of L ligand via N and/or P atoms. The reaction with strong Lewis acid Zn(II) resulted in the rearrangement of PNP to P−P−N moiety and formation of complex 3. The structures of L, 2−5 were determined by single crystal X-ray (XRD) diffraction, while that of 1•0.75C 7 H 8 was determined by powder XRD analysis. Intermolecular secondary bonding of S•••S interactions in the compounds, unusual for benzothiadiazoles, was discussed supported by quantum chemical calculations. Differences in the structures of the compounds cause significant changes of photophysical properties. In particular, the position of the electronic absorption band is featured by the conformation of L, viz., the dihedral angle between the benzothiadiazole unit and the PNP moiety, as proved by TD-DFT calculations performed on model molecules. The photophysical properties of the compounds also strongly depend on the coordination mode of L: the presence of a bond between the metal and the N atom of the thiadiazole unit plays an essential role in defining the position of the absorption and emission bands as well as emission lifetime of these compounds. The thermally activated delayed fluorescence and phosphorescence mechanisms in a thermal equilibrium were determined for 1• 0.75C 7 H 8 . Complex 5 features a broad emission band spanning the entire visible region; moreover, it shows an unusual clear-white luminescence, which remains visible even in the daylight.

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“…All values of these optical parameters are shown in Table 6 and the corresponding spectrum is plotted in Figure 7. The spectra show similar profile for all compounds which present a main intense band at higher energies in the visible region ranging from 519.30 to 521.14 nm, and were assigned to the intramolecular charge transfer (IC T) transitions, these strongest absorption peaks arise from The photoluminescence (PL) spectra observed of the studied compound M1 show a broad emission band at 598 nm (Table 7); this could be explained by an electronic transition process that is the reverse of the absorption corresponding mainly to the LUMO-HOMO electron transition configuration [42] . The Stokes Shift is found to be 0.316 eV, it is defined as the difference between the absorption and emission maxima (EVA-EVE), he is linked related to the bandwidths of both absorption and emission bands [43] .…”

Section: Absorption Propertiesmentioning

confidence: 99%

Organic materials based on thiophene and benzothiadiazole for organic solar cells. Computational investigations

Kacimi

Chemek

Azaid

et al. 2020

OAJ Materials and Devices

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In this paper, wepresent new organics chemical structures of pendant phenyl ester-substituted thiophene and benzothiadiazole based copolymers leading to donor (D)-acceptor (A) structure-types. Geometrics and photo-physical properties of the studied chemical structure are exploited in the further ground and excited-state. Theoretically, using the DFT and TD-DFT quantum chemical calculation implanted in Gaussian09 software, geometrical and electronic parameters such as the energy of HOMO and LUMO level, the Egap= EHomo- E Lumo and focused electronic parameters of the molecules were determined. It is obvious that the studied molecules show good photovoltaic properties. Thus, studied chemical structures are blended with acceptor compounds such as fullerene and PCBM derivatives in bulk-heterojunction solar cell. Quantic chemical calculations show that the studied compound present good electronic, optical and photovoltaic properties and can be used as potential electron donors in organic solar cells Heterojunction (BHJ).

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Electronic structure and charge-transport properties of symmetric linear condensed bis-benzothiadiazole derivatives

Cited by 7 publications

References 50 publications

Charge Mobility in Discotic Liquid Crystals

Charge Mobility in Discotic Liquid Crystals

Tuning of the Coordination and Emission Properties of 4-Amino-2,1,3-Benzothiadiazole by Introduction of Diphenylphosphine Group

Organic materials based on thiophene and benzothiadiazole for organic solar cells. Computational investigations

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