Electronic and thermal properties of compounds bearing diimide, azomethine and triphenylamine units

Grucela-Zajac, Marzena; Bijak, Katarzyna; Zaleckas, Ernestas; Grigalevičius, Saulius; Wiacek, Malgorzata; Janeczek, Henryk; Schab‐Balcerzak, Ewa

doi:10.1016/j.optmat.2014.07.020

Cited by 15 publications

(8 citation statements)

References 27 publications

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“…Due to their structure, imide rings can be divided into five- and six-membered rings obtained from phthalic or naphthalene/perylene anhydrides. Many publications associated with imide rings in organic electronics include symmetrical structures (phthalic diimides, naphthalene, perylene) [ 5 , 6 , 7 , 8 , 9 , 10 ]. The imide molecules’ properties can be changed by modifying the substituent type attached to the nitrogen atom or, more broadly, by modifying the perylene or naphthalene ring (4-C or 3-C) [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

“…Many publications associated with imide rings in organic electronics include symmetrical structures (phthalic diimides, naphthalene, perylene) [ 5 , 6 , 7 , 8 , 9 , 10 ]. The imide molecules’ properties can be changed by modifying the substituent type attached to the nitrogen atom or, more broadly, by modifying the perylene or naphthalene ring (4-C or 3-C) [ 9 ]. The introduction of structures with electron-donating properties to the naphthalene ring allows the obtainment of materials with a low band gap, which is beneficial in optoelectronic applications [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

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New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

et al. 2021

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In this paper, six novel symmetrical bis-(imino-1,8-naphthalimides) differing in core and N-substituent structure were synthesized, and their thermal (TGA, DSC), optical (UV-Vis, PL), electrochemical (DPV, CV) properties were evaluated. The compounds were stable to 280 °C and could be transferred into amorphous materials. Electrochemical investigations showed their ability to occur reductions and oxidations processes. They exhibited deep LUMO levels of about −3.22 eV and HOMO levels above −5.80 eV. The optical investigations were carried out in the solutions (polar and non-polar) and in films and blends with PVK:PBD. Bis-(imino-1,8-naphthalimides) absorbed electromagnetic radiation in the range of 243–415 nm and emitted light from blue to yellow. Their capacity for light emission under voltage was preliminarily tested in devices with an active layer consisting of a neat compound and a blend with PVK:PBD. The diodes emitted green or red light.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

et al. 2021

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“…On the other hand, several studies have reported the use of azomethine in molecular systems used in photovoltaics devices, finding an improvement in the luminescent properties and the molecular structures stability [29] and considering the azomethine as a photo-stable group [30] and with a good electric conductance [31]. Therefore, it is expected that azomethine is beneficial to charge transportation and has potential application to produce high-quality organic semiconductors [32]. Further, azomethine has been used in applications such as organic light-emitting diodes (OLEDs) [33,34,35], OFET [36,37], and DSSC [38,39].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Effect of Different π Bridges Including an Azomethine Group in Triphenylamine-Based Dye for Dye-Sensitized Solar Cells

et al. 2019

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Ten molecules were theoretically calculated and studied through density functional theory with the M06 density functional and the 6-31G(d) basis set. The molecular systems have potential applications as sensitizers for dye-sensitized solar cells. Three molecules were taken from the literature, and seven are proposals inspired in the above, including the azomethine group in the π-bridge expecting a better charge transfer. These molecular structures are composed of triphenylamine (donor part); different combinations of azomethine, thiophene, and benzene derivatives (π-bridge); and cyanoacrylic acid (acceptor part). This study focused on the effect that the azomethine group caused on the π-bridge. Ground-state geometry optimization, the highest occupied molecular orbital, the lowest unoccupied molecular orbital, and their energy levels were obtained and analyzed. Absorption wavelengths, oscillator strengths, and electron transitions were obtained via time-dependent density functional theory using the M06-2X density functional and the 6-31G(d) basis set. The free energy of electron injection (ΔGinj) was calculated and analyzed. As an important part of this study, chemical reactivity parameters are discussed, such as chemical hardness, electrodonating power, electroaccepting power, and electrophilicity index. In conclusion, the inclusion of azomethine in the π-bridge improved the charge transfer and the electronic properties of triphenylamine-based dyes.

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“…5 Currently, because of the high thermal stability, good mechanical property, and excellent chemical stability, some super engineering plastic polymers such as polyimides, 6 polyarylsulfones, 7,8 and polyetherketones 9 have been considered to build the abovementioned organic photoelectronic materials. So far, many polyimide-based polymers with TPAs or other electro-optical moieties have been synthesized and investigated as electroluminescent materials, [10][11][12][13] electrochromism materials, 6,[14][15][16][17][18][19][20][21][22] and memory storage materials. 7,[23][24][25] Polyarylsulfones (PASs), a kind of high thermal stability amorphous polymers, can be adopted for the abovementioned applications similar to polyimides.…”

Section: Introductionmentioning

confidence: 99%

Direct synthesis of triphenylamine-containing polyarylsulfones from commercially available aniline

Chen

Lin

Sun

et al. 2016

High Performance Polymers

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A novel triphenylamine-containing polyarylsulfone (PAS-TPA) was synthesized from commercially available aniline and 1,1′-sulfonylbis(4-fluorobenzene) via two-step N–C coupling reaction under nucleophilic substitution polycondensation condition. Subsequently, a new series of polysulfones with different TPA contents (PSU-TPAs) was developed by the same method. Both PAS-TPA and PSU-TPAs not only exhibited good thermal stability and solubility but also exhibited intense ultraviolet absorption and fluorescence and high fluorescence quantum yield (approximately 16–42%). Their ideal highest occupied molecular orbital level (approximately −5.5 to −5.6) indicated the potential application of these polymers in organic photoelectronic fields.

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Electronic and thermal properties of compounds bearing diimide, azomethine and triphenylamine units

Cited by 15 publications

References 27 publications

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

Theoretical Study of the Effect of Different π Bridges Including an Azomethine Group in Triphenylamine-Based Dye for Dye-Sensitized Solar Cells

Direct synthesis of triphenylamine-containing polyarylsulfones from commercially available aniline

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