Multifunctional derivatives of donor-substituted perfluorobiphenyl for OLEDs and optical oxygen sensors

Danyliv, Iryna; Danyliv, Yan; Lytvyn, R. Z.; Bezvikonnyi, Oleksandr; Volyniuk, Dmytro; Simokaitienė, Jūratė; Ivaniuk, Khrystyna; Tsiko, Uliana; Tomkevičienė, Aušra; Dabulienė, Asta; Skuodis, Eigirdas; Stakhira, Pavlo

doi:10.1016/j.dyepig.2021.109493

Cited by 12 publications

(7 citation statements)

References 59 publications

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“…Compared to the compound SM3 (Fig. 7), the HOMO orbitals were delocalized throughout the molecule, and due to the high electronegativity of the fluorine atoms, the LUMO orbitals were mainly on the PFBP fragment [37].…”

Section: Structure Modifications In the Design Strategy Of Conjugated...mentioning

confidence: 91%

“…8) developed by I. Danyliv et al based on PFBP (per-fluorobiphenyl; acceptor) and DPA (donor) are also promising in modern OLED technology. Their synthesis was based on a one step, catalyst-free aromatic nucleophilic substitution reaction (Scheme 1) [37]. HOMO values were -5.9 eV and -5.7 eV, while LUMO values were -2.1 eV and -1.9 eV (for DPA-PFBP-A and DPA-PFBP-B, respectively).…”

Section: Structure Modifications In the Design Strategy Of Conjugated...mentioning

confidence: 99%

“…Muthusankar et al [44] presented the results of their research, in which they obtained a glucose biosensor with a 5 s response time, in the concentration range from 1 to 10 µM, Scheme 1 Synthetic route of DPA-PFBP-A and DPA-PFBP-B [37] Fig. 9 a Chemical structure of azaryl ketone (pBZ) [31].…”

Section: Electrofluorochromismmentioning

confidence: 99%

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Derivatives of diphenylamine and benzothiadiazole in optoelectronic applications: a review

2022

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Light-emitting conjugated organic compounds have found special interest among researchers. Because of their adjustable optoelectronic properties they can be applied in e.g. field-effect transistors, sensors, light-emitting diodes or photovoltaic cells. In order to develop high-performance systems, it is important to understand the relationship between the structure and the photophysical properties of the material used. One of the employed strategies is to decrease the band gap of conjugated compounds, often achieved through a “donor–acceptor” approach. One of the popular groups applied as an electron-accepting unit are benzothiadiazoles, while diphenylamine exhibits good electron-donating ability. The functional groups can affect the energy levels of materials, influencing the color of the light emitted. This work presents a review of research focused on the structure-properties relationship of diphenylamine and benzothiadiazole derivatives with optoelectronic applications.

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Section: Structure Modifications In the Design Strategy Of Conjugated...mentioning

confidence: 91%

Section: Structure Modifications In the Design Strategy Of Conjugated...mentioning

confidence: 99%

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Derivatives of diphenylamine and benzothiadiazole in optoelectronic applications: a review

2022

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“…To overcome this issue, employ hot exciton materials. These materials utilize reverse intersystem crossing from higher triplet (T 2 , T n ) to singlet states, effectively harnessing non‐radiative triplet excitons [8] . Later, Adachi et al.…”

Section: Introductionmentioning

confidence: 99%

Converting Conventional Host to TADF Sensitizer and Hot‐Exciton Emitter in Donor‐Adamantane‐Acceptor Triads for Blue OLEDs: A Computational Study

Mahaan,

Bosco,

Jothi

2024

ChemPhotoChem

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Exploiting triplet excitons in TADF sensitizers and hot‐exciton emitters has attracted considerable attention and interest in recent studies on the design and development of blue OLEDs. The structural and optical property relationship of adamantane (Ad) core appended with four different strengths of donor and seven acceptor units were investigated using DFT and TD‐DFT methods. The theoretical studies revealed that increased donor and acceptor strength on adamantane building block leads to: (i) a decrease in ionization potentials and an increase in electron affinities, (ii) a decrease in singlet energies (ES) and the S1‐T1 energy gaps (∆EST); (iii) decreased SOC magnitudes between S1‐T1 states; (iv) increased RISC rate from the Tn to S1 states, demonstrating an increased tendency for upconversion of triplet excitons from the Tn to S1 state. In addition, low exchange energy causes excited state characteristics of molecules to shift from HLCT to CT nature in the S1 state. In contrast, the T1 states retain their LE character, resulting in higher triplet energies (ET). The adamantane molecular systems appended with P‐DMAC‐Donor‐Ad‐P‐DMB and Donor‐Ad‐P‐BODIPY based triads exhibit promising TADF sensitizer and hot‐exciton characteristics to find application as potential candidates for blue OLEDs when compared to experimentally reported conventional host.

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“…Numerous studies have focused on devices based on polymers with an incorporated carbazole building block [ 18 , 19 , 20 , 21 ]. Carbazole derivatives are an effective host material for phosphorescent additives in PhOLEDs [ 15 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ], an active component of fluorescent OLEDs with thermally activated delayed fluorescence (TADF) [ 14 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ] or molecules with a hybridized local and charge state of transfer (HLCT) [ 44 , 45 , 46 , 47 , 48 , 49 , 50 ]. Computer-aided design is also currently being used to suggest more stable and more efficient organic diodes [ 51 ].…”

Section: Introductionmentioning

confidence: 99%

Structure and Conformational Mobility of OLED-Relevant 1,3,5-Triazine Derivatives

et al. 2023

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A series of OLED-relevant compounds, consisting of 1,3,5-triazine core linked to various aromatic arms by amino group, has been synthesized and characterized. The studied compounds exist in solution as a mixture of two conformers, a symmetric propeller and asymmetric conformer, in which one of the aromatic arms is rotated around the C-N bond. At temperatures below −40 °C, the VT NMR spectra in DMF-d7 are in a slow exchange regime, and the signals of two conformers can be elucidated. At temperatures above 100 °C, the VT NMR spectra in DMSO-d6 are in a fast exchange regime, and the averaged spectra can be measured. The ratio of symmetric and asymmetric conformers in DMF-d7 varies from 14:86 to 50:50 depending on the substituents. The rotational barriers of symmetric and asymmetric conformers in DMF-d7 were measured for all compounds and are in the interval from 11.7 to 14.7 kcal/mol. The ground-state energy landscapes of the studied compounds, obtained by DFT calculations, show good agreement with the experimental rotational barriers. The DFT calculations reveal that the observed chemical exchange occurs by the rotation around the C(1,3,5-triazine)-N bond. Although some of the compounds are potentially tautomeric, the measured absorption and emission spectra do not indicate proton transfer neither in the ground nor in the excited state.

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Multifunctional derivatives of donor-substituted perfluorobiphenyl for OLEDs and optical oxygen sensors

Cited by 12 publications

References 59 publications

Derivatives of diphenylamine and benzothiadiazole in optoelectronic applications: a review

Derivatives of diphenylamine and benzothiadiazole in optoelectronic applications: a review

Converting Conventional Host to TADF Sensitizer and Hot‐Exciton Emitter in Donor‐Adamantane‐Acceptor Triads for Blue OLEDs: A Computational Study

Structure and Conformational Mobility of OLED-Relevant 1,3,5-Triazine Derivatives

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