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Балакирев, А. Е.; Майзлиш, В. Е.; Shaposhnikov, G. P.

doi:10.1023/a:1015406625722

Cited by 7 publications

(10 citation statements)

References 2 publications

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“…The synthesis described in the literature includes several steps, some of which proceed with low yields, as shown in Scheme 1. [10,[14][15][16] Additionally, the starting material 1,2-dibromo-4,5-dinitrobenzene is not commercially available and needs to be prepared as well.…”

Section: Synthesismentioning

confidence: 99%

“…[10] We have studied the UV/Vis spectra of 5 in the presence of bases. The UV/Vis spectrum of 5 in THF, CHCl 3 or pyridine corresponds to a "neutral monomeric form" of the triazoleannulated phthalocyanine complex 5 [see Figures 1 and 2 and Table 1; for log(ε) values in CHCl 3 /0.1 % Py see Exp.…”

Section: Uv/vis Spectramentioning

confidence: 99%

“…[8,9] 1,2,3-Triazole-functionalized phthalocyanines, which are especially interesting, have not been reported yet, besides a poorly characterized [tetra(triazolo)phthalocyaninato]cobalt compound. [10] The only reported property of the latter is its solubility in water/ alkali solution. Additionally, its UV/Vis spectra in DMF, concentrated H 2 SO 4 , and aqueous NaOH were tabulated.…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, its UV/Vis spectra in DMF, concentrated H 2 SO 4 , and aqueous NaOH were tabulated. [10] It is known, that imidazolo-or triazolo-porphyrazine derivatives, both symmetrical and unsymmetrical, with free NH function of the fused heterocycle rings were not formed in a cyclotetramerization reaction of the corresponding dinitriles. [8a,9c] Therefore, it is of interest whether the unsymmetrical triazole-annulated phthalocyanine with a free triazole NH group can be obtained in a statistical cross-condensation from the suitable phthalodinitriles.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of an Unsymmetrical Triazole‐Functionalized (Phthalocyaninato)zinc Complex

et al. 2005

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The synthesis of 5,6-dicyano-1H-1,2,3-benzotriazole (2) was significantly simplified and its overall yield was increased. This opens up the possibility for an extended use of 2 as a precursor for triazole-functionalized phthalocyanines. One of them, the unsymmetrical {9, 10,16,17,23,24-hexakis(3,5-ditert-butylphenoxy) [1,2,3]triazolo [4,5-b]phthalocyaninato}-zinc (5) was prepared in a statistical condensation of 2 and 4,5-bis(3,5-di-tert-butylphenoxy)phthalonitrile (3) with subsequent separation by column chromatography. The triazolefunctionalized (phthalocyanine)zinc complex 5 shows inter-

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Section: Synthesismentioning

confidence: 99%

Section: Uv/vis Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of an Unsymmetrical Triazole‐Functionalized (Phthalocyaninato)zinc Complex

et al. 2005

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“…However, a completely different synthetic approach was used: 5,6-dicyano-1H-benzotriazole was prepared first, and then it was used to synthesize tetra- [39] and monotriazolophthalocyanines. [40] 1N-Amination of the latter compound and oxidation of the resulting amino derivative resulted in the generation of a dehydrophthalocyanine, which could be trapped in situ with several dienes to afford the corresponding Diels-Alder adducts.…”

Section: Dedicated To Professor Miha Tišler On the Occasion Of His 80mentioning

confidence: 99%

[1,2,3]Triazolo[4,5‐b]porphyrins: New Building Blocks for Porphyrinic Materials

et al. 2006

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Highly Efficient Red–Orange Delayed Fluorescence Emitters Based on Strong π‐Accepting Dibenzophenazine and Dibenzoquinoxaline Cores: toward a Rational Pure‐Red OLED Design

Furue

Matsuo

Ashikari

et al. 2018

Advanced Optical Materials

178

107

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Organic luminescent materials that exhibit thermally activated delayed fluorescence (TADF) can harvest both singlet and triplet excitons for light emission, leading to high electroluminescence (EL) quantum efficiencies in organic light‐emitting diodes (OLEDs). However, efficient red TADF materials are still very rare because of their restricted molecular design based on the energy gap law. To address this issue, elaborate π‐conjugated donor–acceptor (D–A) systems that can simultaneously achieve a large fluorescence radiative rate and small singlet–triplet energy splitting should be strategically designed. In this study, to produce high‐efficiency pure‐red TADF materials, a remarkably strong π‐accepting dicyanodibenzo[a,c]phenazine (CNBPz) unit has been introduced in a D–π–A molecular framework, and combined with a phenylene‐linked p‐ditolylamine or 9,9‐dimethylacridan moiety. The steady‐state and time‐resolved photophysical measurements revealed intense genuine red TADF emissions of these CNBPz‐based molecules in both solution and doped thin films. The OLEDs incorporating the CNBPz‐based TADF emitters achieve the desired high‐efficiency pure‐red EL, centered at 670 nm with color coordinates of (0.66, 0.34), accompanied by a high maximum external EL quantum efficiency of 15.0%. Therefore, it is concluded that CNBPz, with its expanded π‐conjugation and strong electron‐accepting characteristics, is a particularly useful building unit to design long‐wavelength TADF materials that can overcome the intrinsic energy gap law obstacle.

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Untitled

Cited by 7 publications

References 2 publications

Synthesis and Properties of an Unsymmetrical Triazole‐Functionalized (Phthalocyaninato)zinc Complex

Synthesis and Properties of an Unsymmetrical Triazole‐Functionalized (Phthalocyaninato)zinc Complex

[1,2,3]Triazolo[4,5‐b]porphyrins: New Building Blocks for Porphyrinic Materials

Highly Efficient Red–Orange Delayed Fluorescence Emitters Based on Strong π‐Accepting Dibenzophenazine and Dibenzoquinoxaline Cores: toward a Rational Pure‐Red OLED Design

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