Bipolar 1,8-naphthalimides showing high electron mobility and red AIE-active TADF for OLED applications

Masimukku, Naveen; Gudeika, Dalius; Volyniuk, Dmytro; Bezvikonnyi, Oleksandr; Simokaitienė, Jūratė; Матулис, Вадим Э.; Lyakhov, Dmitry; Azovskyi, Volodymyr; Gražulevičius, Juozas V.

doi:10.1039/d1cp05942d

Cited by 19 publications

(15 citation statements)

References 62 publications

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“…Luminescence lifetimes of compounds were recorded with an OB920 luminescence lifetime spectrometer (Edinburgh Instruments Ltd., U.K.). NI-PTZ , NI-PTZ-O , NI-PTZ 2 , NI-Ph-PTZ , and NI-PhMe 2 -PTZ were prepared according to the literature methods [ 21 , 59 ].…”

Section: Methodsmentioning

confidence: 99%

“…Compound NI-PhMe 2 -PTZ was synthesized in a manner similar to [ 21 ]. Under N 2 atmosphere, compound 3 (142 mg, 0.290 mmol), phenothiazine (69.3 mg, 0.348 mmol), Pd(OAc) 2 (11.7 mg, 0.052 mmol), and sodium tert -butoxide (182.4 mg, 1.898 mmol) were dissolved in dry toluene (5 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Recently, we and others found that the orthogonal donor-acceptor dyad derived from 1,8-naphthalimide (NI) and phenothiazine (PTZ) shows TADF in the red spectral range [20][21][22]. Our purpose of designing that dyad was to study the spin-orbit charge-transfer ISC (SOCT-ISC), i.e., to determine, if the ISC is enhanced by the charge recombination (CR) in the orthogonal dyad.…”

Section: Introductionmentioning

confidence: 99%

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Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

Ye¹,

Cao²,

Raamsdonk³

et al. 2022

Beilstein J. Org. Chem.

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In order to investigate the joint influence of the conformation flexibility and the matching of the energies of the charge-transfer (CT) and the localized triplet excited (3LE) states on the thermally activated delayed fluorescence (TADF) in electron donor–acceptor molecules, a series of compact electron donor–acceptor dyads and a triad were prepared, with naphthalimide (NI) as electron acceptor and phenothiazine (PTZ) as electron donor. The NI and PTZ moieties are either directly connected at the 3-position of NI and the N-position of the PTZ moiety via a C–N single bond, or they are linked through a phenyl group. The tuning of the energy order of the CT and LE states is achieved by oxidation of the PTZ unit into the corresponding sulfoxide, whereas conformation restriction is imposed by introducing ortho-methyl substituents on the phenyl linker, so that the coupling magnitude between the CT and the 3LE states can be controlled. The singlet oxygen quantum yield (ΦΔ) of NI-PTZ is moderate in n-hexane (HEX, ΦΔ = 19%). TADF was observed for the dyads, the biexponential luminescence lifetime are 16.0 ns (99.9%)/14.4 μs (0.1%) for the dyad and 7.2 ns (99.6%)/2.0 μs (0.4%) for the triad. Triplet state was observed in the nanosecond transient absorption spectra with lifetimes in the 4–48 μs range. Computational investigations show that the orthogonal electron donor–acceptor molecular structure is beneficial for TADF. These calculations indicate small energetic difference between the 3LE and 3CT states, which are helpful for interpreting the ns-TA spectra and the origins of TADF in NI-PTZ, which is ultimately due to the small energetic difference between the 3LE and 3CT states. Conversely, NI-PTZ-O, which has a higher CT state and bears a much more stabilized 3LE state, does not show TADF.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

Ye¹,

Cao²,

Raamsdonk³

et al. 2022

Beilstein J. Org. Chem.

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“…Despite M062X, wB97XD and CAM-B3LYP functionals provide accurate reproduction of the absorption spectra with respect to both intensity and the relative peak position, 26,27 these functionals in most cases significantly underestimate the wavelengths of absorption maxima. 20,[25][26][27][28] Therefore, for the comparison of the calculated positions of the first maxima with the experimental ones, we scaled the calculated results using correlation equations from our previous paper. 20 The corresponding correlation equations for each functional are given under the Table 1 and Tables S1 and S2 (ESI †).…”

Section: Theoretical Calculationsmentioning

confidence: 99%

Theoretical and experimental insights into the properties of donor–σ–acceptor type derivatives of quinoxaline and methanone containing different donor moieties

et al. 2022

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“…Among the n-type semiconductors, the imides have been widely studied as compounds for applications in organic electronics [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. The ability to self-organize, accompanied by high thermal stability, and chemical and oxidation resistance, render the naphthalimides good acceptor-donor materials [ 19 , 20 , 21 , 22 , 23 , 24 ]. In addition, the 1,8-naphthalimide derivatives were also used as dyes for cell imaging and as probes or sensors [ 25 , 26 , 27 , 28 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Six New Unsymmetrical Imino-1,8-naphthalimide Derivatives Substituted at 3-C Position—Photophysical Investigations

et al. 2022

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In this research, six novel unsymmetrical imino-1,8-naphthalimides (AzNI) were synthesized. Comprehensive thermal (thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), optical (UV-Vis, photoluminescence), and electrochemical (CV, DPV) studies were carried out to characterize these new compounds. The molecules showed the onset of thermal decomposition in the temperature range 283–372 °C and molecular glass behavior. Imino-1,8-naphthalimides underwent reduction and oxidation processes with the electrochemical energy band gap (Eg) below 2.41 eV. The optical properties were evaluated in solvents with different polarities and in the solid-state as a thin films and binary blends with poly(N-vinylcarbazole): (2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole) (PVK:PBD). Presented compounds emitted blue light in the solutions and in the green or violet spectral range in the solid-state. Their ability to emit light under external voltage was examined. The devices with guest-host structure emitted light with the maximum located in the blue to red spectral range of the electroluminescence band (EL) depending on the content of the AzNI in the PVK:PBD matrix (guest-host structure).

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Bipolar 1,8-naphthalimides showing high electron mobility and red AIE-active TADF for OLED applications

Abstract: Aiming to design bipolar organic semiconductors with high electron mobility and efficient red thermally activated delayed fluorescence (TADF), three donor-acceptor compounds were designed and synthesized selecting 1,8-naphthalimide as acceptor and...

Cited by 19 publications

References 62 publications

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

Theoretical and experimental insights into the properties of donor–σ–acceptor type derivatives of quinoxaline and methanone containing different donor moieties

Six New Unsymmetrical Imino-1,8-naphthalimide Derivatives Substituted at 3-C Position—Photophysical Investigations

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