Design, Synthesis and Opto-electrochemical Properties of Novel Donor–Acceptor Based 2,3-di(hetero-2-yl)pyrido[2,3-b]pyrazine amine derivatives as Blue-Orange Fluorescent Materials

Mahadik, Suraj S.; Garud, Dinesh R.; Ware, Anuja P.; Pingale, Shirish S.; Kamble, Rajesh M.

doi:10.1016/j.dyepig.2020.108742

Cited by 31 publications

(16 citation statements)

References 86 publications

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“…As for donor pat, we selected dihydrophenazasiline (DHPAzSi), as DHPAzSi compounds serve as a moderate electron donor, due to the operation of σ*(CÀ Si)-π hyperconjugation, thereby allowing for the 1 CT state in proximity to a higher triplex excited state (T n ) to undergo (reverse) intersystem crossing via T n state. [10] Although DÀ A type organic photofunctional materials containing the pyrido[2,3-b]pyrazine as the acceptor have recently been developed by several groups, [16][17][18][19][20] TADF emitters based on the pyrido[2,3-b]pyrazine-acceptor and dihydrophenazasiline donor have been unknown. Herein, we disclose the synthesis and photophysical properties of a new family of DÀ A type purely organic TADF emitters 1-3 (Figure 1), using the dihydrophenazasiline as the donor and pyrido[2, 3b]pyrazine as the acceptor.…”

Section: Introductionmentioning

confidence: 99%

A New Entry to Purely Organic Thermally Activated Delayed Fluorescence Emitters Based on Pyrido[2,3‐b]pyrazine‐Dihydrophenazasilines Donor‐Acceptor Dyad

et al. 2022

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A new family of thermally activated delayed fluorescence (TADF) emitters based on a twisted donoracceptor (DÀ A) dyad scaffold comprising of dihydrophenazasiline (D) and pyrido[2,3-b]pyrazine (A) has been developed, and their properties have been investigated. Time-resolved spectroscopic analysis in matrices revealed the detailed photophysical properties of the DÀ A compounds. These DÀ A compounds serve as the emitter for organic light-emitting diodes (OLEDs), showing a moderate external quantum efficiency (EQE) up to 9% in CBP matrix. Furthermore, theoretical calculations uncovered the excited states nature of the developed TADF emitters.

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Section: Introductionmentioning

confidence: 99%

A New Entry to Purely Organic Thermally Activated Delayed Fluorescence Emitters Based on Pyrido[2,3‐b]pyrazine‐Dihydrophenazasilines Donor‐Acceptor Dyad

et al. 2022

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“…The presence of both of these features is consistent with either a delocalized or ILCT nonemissive state for the monothiophenesubstituted systems and thiophene-localized states for the biand terthiophene-substituted systems. As the lifetimes of these nonemissive states are much longer than for the 1 ILCT states observed in transient emission (TE) spectroscopy and show sensitivity to the presence of 3 O 2 , they are assigned as being triplet in nature.…”

Section: ■ Introductionmentioning

confidence: 97%

“…The ■ RESULTS AND DISCUSSION Synthesis and Characterization. The synthesis of the target compounds is presented in Scheme 1. btd-1T and btd-2T were prepared in one high-yielding step from 5bromobenzo[c] [1,2,5]thiadiazole through Suzuki-Miyaura couplings with the corresponding pinacolatoboronic ester. btd-3T was prepared in three steps from 5-bromobenzo[c]- [1,2,5]thiadiazole: Suzuki-Miyaura coupling with 2-thienylboronic acid, selective bromination at the 5-position of the thienyl group, and Suzuki-Miyaura coupling with 5′-hexyl-2,2′-thien-5ylboronic acid pinacol ester to afford btd-3T in an overall yield of 42%.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The synthesis of the target compounds is presented in Scheme 1. btd-1T and btd-2T were prepared in one high-yielding step from 5bromobenzo[c] [1,2,5]thiadiazole through Suzuki-Miyaura couplings with the corresponding pinacolatoboronic ester. btd-3T was prepared in three steps from 5-bromobenzo[c]- [1,2,5]thiadiazole: Suzuki-Miyaura coupling with 2-thienylboronic acid, selective bromination at the 5-position of the thienyl group, and Suzuki-Miyaura coupling with 5′-hexyl-2,2′-thien-5ylboronic acid pinacol ester to afford btd-3T in an overall yield of 42%. Conversion of btd compounds to dppz ligands was achieved using CoCl 2 -catalyzed NaBH 4 reduction and sulfur abstraction, followed by Schiff-base condensation with 1,10phenanthroline-5,6-dione, in yields ranging from 21% to 42%.…”

Section: ■ Introductionmentioning

confidence: 99%

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Transitioning from Intraligand π,π* to Charge-Transfer Excited States Using Thiophene-Based Donor–Acceptor Systems

et al. 2020

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A series of electron donor–acceptor compounds are reported in which both the donor and acceptor strengths are systematically altered using mono-, bi-, and terthiophene as donors and benzo[c][1,2,5]thiadiazole (btd), dipyrido[3,2-a:2′,3′-c]phenazine (dppz), and the corresponding rhenium(I) complex, [ReCl(CO)3(dppz)], as acceptors. The electronic properties of the compounds are characterized using electrochemistry, electronic absorbance and emission spectroscopies, and transient absorption spectroscopy. The effect of donor and acceptor strengths on frontier molecular orbital localization and on the charge-transfer (CT) character of optical transitions is modeled using density functional theory (DFT) calculations. The electronic absorption spectra of the compounds investigated are dominated by intraligand charge-transfer (ILCT) transitions, where the CT character is shown to increase across the series from mono- to bi- to terthiophene but not significantly across the acceptor series. Emission is shown to originate from the absorbing state. Long-lived nonemissive states have been observed using transient absorption spectroscopy and assigned using triplet-state DFT calculations, which indicate that the lowest energy excited state has more thiophene-localized π,π* character with an increasing number of appended thiophenes.

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“…Organic semiconductors are currently used in many fields of science, e.g., organic light-emitting diode (OLED), solar cells, transistors, molecular imaging, and sensors [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. Due to their conductive and optical properties, the possibility of easy modification, flexibility, and low production costs, they displace their inorganic counterparts.…”

Section: Introductionmentioning

confidence: 99%

2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties

et al. 2021

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We herein report the design and synthesis of small-donor molecules, 2,1,3-benzothiadiazole derivatives (2a–d), by Stille or Suzuki reaction. The synthesized compounds were characterized by spectroscopic and electrochemical methods. The compounds 2a–d absorb the light in a wide range (the UV-green/yellow light (2c)) and emit from green to red/near IR light (2c). Furthermore, these compounds show a narrow energy gap (1.75–2.38 eV), and high Ea values increasing for polymers, which prove their electron-donating nature and semiconductor properties. The measurements were enhanced by theoretical modeling.

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Design, Synthesis and Opto-electrochemical Properties of Novel Donor–Acceptor Based 2,3-di(hetero-2-yl)pyrido[2,3-b]pyrazine amine derivatives as Blue-Orange Fluorescent Materials

Cited by 31 publications

References 86 publications

A New Entry to Purely Organic Thermally Activated Delayed Fluorescence Emitters Based on Pyrido[2,3‐b]pyrazine‐Dihydrophenazasilines Donor‐Acceptor Dyad

A New Entry to Purely Organic Thermally Activated Delayed Fluorescence Emitters Based on Pyrido[2,3‐b]pyrazine‐Dihydrophenazasilines Donor‐Acceptor Dyad

Transitioning from Intraligand π,π* to Charge-Transfer Excited States Using Thiophene-Based Donor–Acceptor Systems

2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties

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