The synthesis of aromatic diazatricycles from phenylenediamine-bis(methylene Meldrum's acid) derivatives

Graf, Gabriele Ina; Hastreiter, Daniel; Silva, Luiz Everson da; Rebelo, Ricardo Andrade; Montalbán, Antonio; McKillop, Alexander

doi:10.1016/s0040-4020(02)01085-2

Cited by 40 publications

(31 citation statements)

References 26 publications

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“…[62][63][64] Standard procedures were used to dry the solvents. Unless otherwise stated, all reagents were used as received without further purification.…”

Section: Methodsmentioning

confidence: 99%

Tailoring Optoelectronic Properties of Phenanthroline‐Based Thermally Activated Delayed Fluorescence Emitters through Isomer Engineering

Zhang

Zhan

et al. 2016

Advanced Optical Materials

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Three isomeric phenanthroline compounds, namely o-PXZP, m-PXZP, and p-PXZP, are constructed by incorporating electron-donor phenoxazine unit into ortho-, meta-, or para-positions of a rigid electron-acceptor phenanthroline core. This approach functionalizes these compounds to exhibit thermally activated delayed fluorescence (TADF) characteristics with microsecondscale photoluminescence (PL) lifetimes. Their thermal, electrochemical properties, emissive characteristics, and energy levels can be finely tailored through isomer engineering. The meta-and para-linking compounds (m-PXZP and p-PXZP) possess higher decomposition temperatures, deeper lowest unoccupied molecular orbital levels, higher PL quantum efficiencies, smaller singlet-triplet energy splitting, and reduced DF lifetimes relative to their ortho-disposition isomer (o-PXZP). Consequently, a green fluorescence organic light-emitting diode (OLED) based on m-PXZP achieves a maximum external quantum efficiency of 18.9%, and has a slow efficiency roll-off of 28% at the luminance of 1000 cd m −2 . Notably, m-PXZP-based device exhibits a nearly 100% utilization efficiency of electro-generated singlet and triplet excitons. These results demonstrate for the first time that phenanthroline derivatives can be employed as TADF emitters for high-efficiency OLEDs. The isomer engineering for TADF emitters provides a simple method to extend structure diversity of TADF emitters, and moreover it provides a flexible method to optimize optoelectronic properties and thereby manipulate electroluminescence performance.

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“…[62][63][64] Standard procedures were used to dry the solvents. Unless otherwise stated, all reagents were used as received without further purification.…”

Section: Methodsmentioning

confidence: 99%

Tailoring Optoelectronic Properties of Phenanthroline‐Based Thermally Activated Delayed Fluorescence Emitters through Isomer Engineering

Zhang

Zhan

et al. 2016

Advanced Optical Materials

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“…This can be attributed to better charge distribution in the angularWheland type intermediate as observed by Graf et al [24]. The treatment of compound 9 with phosphoryl chloride and phosphorus pentachloride furnished the unexpected 4,5,6,8, 9-Pentachloro-10-oxo-pyrimido[1,2-a]1,8-naphthyridine (10) in 75% yield (Scheme 3).…”

Section: Chemistrymentioning

confidence: 60%

Synthesis and Antiparasitic Activity Against Trypanosoma cruzi and Leishmania amazonensis of Chlorinated 1,7- and 1,8-Naphthyridines

Silva¹,

Joussef²,

Pacheco³

et al. 2007

LDDD

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The leishmanicidal and trypanocidal activities of chlorinated 1,7-and 1,8-naphthyridines were evaluated against cultured of L. amazonensis promastigote and T. cruzi epimastigote forms. Active compounds were also tested against blood trypomastigotes and their toxicity to Vero cells. Among the compounds evaluated 10 was the most active against L. amazonensis promastigotes and T. cruzi epimastigotes, IC 50 = 8.6 µM and IC 50 = 20.4 µM, respectively.

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“…8,9,29,36,37 It is also known that in the formation of cyclic compounds from phenylenediamine or quinoline derivatives, the angular structure is obtained in preference to the linear one when both are possible. 8,9,29,36 In the present work, only derivatives of the angular structure were obtained, instead of the linear isomer bis-trifluoromethylsubstituted pyrido[g]quinolines (6) (Scheme 2). However, neither of the products isolated showed a mode of cyclization similar to that observed in the product previously identified by us as 2,8-bis(trifluoromethyl)-1,7-phenanthroline (3a).…”

Section: Resultsmentioning

confidence: 99%

“…7 However, phenanthrolines can be also prepared from aminoquinolines. 8 The first phenanthroline, 1,7-phenanthroline was prepared by Skraup and Vortmann 9 in 1882 and the method continues to be one of the best Chemical structure of the non-natural antimalarial halofantrine. Vol.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

Bonacorso

Andrighetto

Krüger

et al. 2011

J. Braz. Chem. Soc.

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The synthesis of aromatic diazatricycles from phenylenediamine-bis(methylene Meldrum's acid) derivatives

Cited by 40 publications

References 26 publications

Tailoring Optoelectronic Properties of Phenanthroline‐Based Thermally Activated Delayed Fluorescence Emitters through Isomer Engineering

Tailoring Optoelectronic Properties of Phenanthroline‐Based Thermally Activated Delayed Fluorescence Emitters through Isomer Engineering

Synthesis and Antiparasitic Activity Against Trypanosoma cruzi and Leishmania amazonensis of Chlorinated 1,7- and 1,8-Naphthyridines

Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

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