Phenoxazine and N-phenyl-1-naphtylamine-based enamines as hole-transporting glass-forming materials

Paspirgelyte, R.; Gražulevičius, Juozas V.; Grigalevičius, Saulius; Jankauskas, Vygintas

doi:10.1016/j.synthmet.2009.01.015

Cited by 16 publications

(6 citation statements)

References 14 publications

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“…[27] A comparison between POZ-and PTZ-based sensitizers showed that the POZ-based dye TH301 gave an efficiency of 6.2 % and the structurally similar PTZ-based T2-1 showed an efficiency of 5.5 % under similar conditions. [25,26] POZ dyes have been used in other applications, such as laser dyes, [31] indicators, [32] biological stains, [33] anticancer agents, [34] hole-transporting materials, [35] and in host-guest systems. [36] There are some general considerations to take into account for the design of a sensitizer for DSCs: 1) strong and broad light absorption for efficient light harvesting, 2) appropriate energy levels for efficient electron injection and dye regeneration, and 3) easy and reliable synthesis with cheap, nontoxic materials suitable for future large-scale production.…”

Section: à2mentioning

confidence: 99%

Phenoxazine Dyes for Dye‐Sensitized Solar Cells: Relationship Between Molecular Structure and Electron Lifetime

Karlsson

Jiang

Eriksson

et al. 2011

Chemistry A European J

108

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A series of metal-free organic dyes with a core phenoxazine chromophore have been synthesized and tested as sensitizers in dye-sensitized solar cells. Overall conversion efficiencies of 6.03-7.40% were reached under standard AM 1.5G illumination at a light intensity of 100 mW cm(-2) . A clear trend in electron lifetime could be seen; a dye with a furan-conjugated linker showed a shorter lifetime relative to dyes with the acceptor group directly attached to the phenoxazine. The addition of an extra donor unit, which bore insulating alkoxyl chains, in the 7-position of the phenoxazine could increase the lifetime even further and, together with additives in the electrolyte to raise the conduction band, an open circuit voltage of 800 mV could be achieved. From photoelectron spectroscopy and X-ray absorption spectroscopy of the dyes adsorbed on TiO(2) particles, it can be concluded that the excitation is mainly of cyano character (i.e., on average, the dye molecules are standing on, and pointing out, from the surface of TiO(2) particles).

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Section: à2mentioning

confidence: 99%

Phenoxazine Dyes for Dye‐Sensitized Solar Cells: Relationship Between Molecular Structure and Electron Lifetime

Karlsson

Jiang

Eriksson

et al. 2011

Chemistry A European J

108

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“…As shown in Scheme , phenothiazine-based enamine derivatives DPE-PTZ-Cl and DPE-PTZ-CF 3 were successfully obtained by a one-step procedure from commercially available 2-chloro-phenothiazine and 2-trifluoromethyl-phenothiazine, which were condensed with 2,2-diphenylacetaldehyde. , Such a typical Stork enamine reaction was catalyzed by (±)-camphor-10-sulfonic acid. Both DPE-PTZ-Cl and DPE-PTZ-CF 3 have good solubility in common organic solvents, such as toluene, chloroform, ethyl acetate, tetrahydrofuran, and dichloromethane.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds DPE-PTZ-Cl and DPE-PTZ-CF 3 were prepared by procedures described in the literature. , In detail, 2-chlorophenothiazine (0.70 g, 3 mmol) was dissolved in 15 mL of toluene. 2,2-Diphenylacetaldehyde (0.59 g, 3 mmol) and a catalytic amount of (±)-camphor-10-sulfonic acid were added to the solution.…”

Section: Experimental Sectionmentioning

confidence: 99%

Phenothiazine-Based Luminophores with AIE, Solvatochromism, and Mechanochromic Characteristics

Huang

Wang

et al. 2021

J. Phys. Chem. B

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Aggregation-induced emission (AIE) fluorescent molecules with unique photoelectric properties have received extensive attention due to the wide range of applications. In this work, two novel phenothiazine-based luminophores DPE-PTZ-Cl and DPE-PTZ-CF 3 were designed based on the frontier molecular orbital (FMO) theory and construction strategy of AIEgens. As expected, both of the luminophores displayed typical AIE behavior and realized the spatial separation of FMOs, which was confirmed by the positive solvatochromism behavior. Their AIE properties could be attributed to the twisted three-dimensional (3D) conformation. Such a conformation resulted from “butterfly-like” phenothiazine and a multirotor structure of diphenylethylene. The spatial separation of FMOs originated from the push–pull electronic synergistic effect of the donor–acceptor (D–A) architecture. Interestingly, DPE-PTZ-Cl also showed a rare blue-shifted mechanochromic (MC) luminescence property. Single-crystal X-ray diffraction (SCXRD) and powder X-ray diffraction (PXRD) experiments were carried out to reveal that the phase transformation between crystalline and amorphous states was responsible for the peculiar solid-state luminescence phenomenon.

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“…Compound DPE-PTZ-CN was prepared by following the procedures described in the literature . In detail, 2-cyanophenothiazine (1.12 g, 5 mmol) was dissolved in 20 mL of toluene.…”

Section: Methodsmentioning

confidence: 99%

R–D–A and R–D−π–A Structured AIEgens: Relationship between Electronic, Conformational Characteristics and Photophysical Properties

Huang

Wang

et al. 2022

J. Phys. Chem. B

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The design of new aggregation-induced emission luminogens (AIEgens) has aroused continuous attention. The relationship between structure and performance plays an important role in guiding such efforts. In this contribution, two R−D−A-and R−D−π−A-type AIEgens were facilely designed and synthesized, that is, DPE-PTZ-CN and DPE-PTZ-PCN, with diphenylethylene as the twisted rotor structure (R), phenothiazine as electron-donor (D), and the (aryl) cyano group as electron-acceptor (A) fragments. Both luminophores were endowed with typical AIE properties, while their α AIE (PL intensity ratio of AIEgen in a mixed solution with water fraction (f w ) = 90 vol % to that with f w = 0) were quite different. The α AIE for DPE-PTZ-CN was as high as 41, but it was only 3 for DPE-PTZ-PCN, in which the π-bridge (aryl linker) was introduced between its D and A groups. In addition, the push−pull electronic effect endowed both molecules with the feature of intramolecular charge transfer (ICT). The solvatochromism effect observed in solutions with different polarities confirmed the existence of the ICT process. The theoretical calculation and single crystal structure analysis revealed that the electronic structure and molecular conformation characteristics had a decisive influence on the differences in photophysical behaviors.

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Phenoxazine and N-phenyl-1-naphtylamine-based enamines as hole-transporting glass-forming materials

Cited by 16 publications

References 14 publications

Phenoxazine Dyes for Dye‐Sensitized Solar Cells: Relationship Between Molecular Structure and Electron Lifetime

Phenoxazine Dyes for Dye‐Sensitized Solar Cells: Relationship Between Molecular Structure and Electron Lifetime

Phenothiazine-Based Luminophores with AIE, Solvatochromism, and Mechanochromic Characteristics

R–D–A and R–D−π–A Structured AIEgens: Relationship between Electronic, Conformational Characteristics and Photophysical Properties

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