Quinoxaline-Embedded Polyacenoquinone Esters: Synthesis, Electronic Properties, and Crystal Structure

Chou, Teh‐Chang; Lin, Kuen-Cheng; Konno, Masaki; Lee, Chih-Ching; Shinmyozu, Teruo

doi:10.1021/ol2017774

Cited by 11 publications

(4 citation statements)

References 47 publications

(22 reference statements)

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“…o-diketones results in azaacenes. In the case of substrates containing hydroxyl groups in addition to keto ones, as in the synthesis with the use of dihydroxybenzoquinone or oxalic acid, dihydroxy derivatives of azaacenes are obtained in the first step, then dihydroazaacenes in the second one, which finally have to be oxidized to tetraazaacenes [45,46]. Optimization of o-diketone condensation with o-diamines (or their salts) leads to various pyrazine derivatives which can be obtained in good yields.…”

Section: Applications Of Azaacenesmentioning

confidence: 99%

“…Over the years, the condensation methods of azaacenes preparation have been constantly modified and improved. In particular, application of protic compounds as solvents or catalytic admixtures led to a significant lowering of the reaction temperature to values below 100 °C (in selected cases even below 50 °C), while retaining high reaction yields [ 44 , 45 , 46 ].…”

Section: Synthesis Of Azaacenesmentioning

confidence: 99%

“…Condensation of aromatic o -diamines with o -dihydroxy derivatives of aryl compounds carried out in mild conditions yields dihydroazaacenes whereas the condensation with o-diketones results in azaacenes. In the case of substrates containing hydroxyl groups in addition to keto ones, as in the synthesis with the use of dihydroxybenzoquinone or oxalic acid, dihydroxy derivatives of azaacenes are obtained in the first step, then dihydroazaacenes in the second one, which finally have to be oxidized to tetraazaacenes [ 45 , 46 ].…”

Section: Synthesis Of Azaacenesmentioning

confidence: 99%

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Azaacenes Based Electroactive Materials: Preparation, Structure, Electrochemistry, Spectroscopy and Applications—A Critical Review

2021

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This short critical review is devoted to the synthesis and functionalization of various types of azaacenes, organic semiconducting compounds which can be considered as promising materials for the fabrication of n-channel or ambipolar field effect transistors (FETs), components of active layers in light emitting diodes (LEDs), components of organic memory devices and others. Emphasis is put on the diversity of azaacenes preparation methods and the possibility of tuning their redox and spectroscopic properties by changing the C/N ratio, modifying the nitrogen atoms distribution mode, functionalization with electroaccepting or electrodonating groups and changing their molecular shape. Processability, structural features and degradation pathways of these compounds are also discussed. A unique feature of this review concerns the listed redox potentials of all discussed compounds which were normalized vs. Fc/Fc+. This required, in frequent cases, recalculation of the originally reported data in which these potentials were determined against different types of reference electrodes. The same applied to all reported electron affinities (EAs). EA values calculated using different methods were recalculated by applying the method of Sworakowski and co-workers (Org. Electron. 2016, 33, 300-310) to yield, for the first time, a set of normalized data, which could be directly compared.

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Section: Applications Of Azaacenesmentioning

confidence: 99%

Section: Synthesis Of Azaacenesmentioning

confidence: 99%

Section: Synthesis Of Azaacenesmentioning

confidence: 99%

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Azaacenes Based Electroactive Materials: Preparation, Structure, Electrochemistry, Spectroscopy and Applications—A Critical Review

2021

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“…A search of the Cambridge Structural Database (V5.38; Groom et al, 2016) for the naphthoquinoxaline core gave three matches each having an additional fused six-membered ring, including the unsubstituted N-heteropentacene pyrazino[2 0 ,3 0 ;6,7]naphtho[2,3-g]quinoxaline-6,13-dione (ref code AROCAM;Liang et al, 2010) and two 13-chloro-6methylcarboxylato-naphtho[2,3-b]phenazine-7,12-diones (ref codes ABUVAW and ABUVEA;Chou et al, 2011). Each of these examples have planar, or only slightly twisted (ca 12 ) polycyclic cores and adopt off-setstacked supramolecular structures.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of two 2,3-diethylnaphtho[2,3-g]quinoxaline-6,11-dione derivatives

Forsyth

Francis

2017

Acta Cryst E

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Two new 5,12-disubstituted 2,3-diethylnaphtho[2,3-g]quinoxaline-6,11-dione compounds were readily synthesized from the commercial dye quinizarin. For 2,3-diethyl-5,12-dihydroxynaphtho[2,3-g]quinoxaline-6,11-dione, (II), C 20 H 16 N 2 O 4 , the molecule displays a near planar conformation and both hydroxy groups participate in intramolecular O-HÁ Á ÁO(carbonyl) hydrogen bonds. In the crystal, -ring interactions [minimum ring centroid separation = 3.5493 (9) Å ] form stacks of co-planar molecules down the c axis, while only minor intermolecular C-HÁ Á ÁO interactions are present. In contrast, in 2,3-diethyl-5,12-bis(piperidin-1-yl)naphtho[2,3-g]quinoxaline-6,11-dione, (IV), C 30 H 34 N 4 O 2 , which contains two independent, but similar, molecules in the asymmetric unit, the polycyclic cores have a significant twist, with dihedral angles of 29.79 (6) and 29.31 (7) between the terminal rings and only minor intermolecular C-HÁ Á ÁO hydrogen-bonding interactions are present. Electron density associated with additional solvent molecules disordered about a fourfold axis was accounted for using the SQUEEZE procedure in PLATON [Spek (2015). Acta Cryst. C71, 9-18].

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Photo‐Induced Functionalization of para‐Benzoquinones: Access to Dihydroquinoxalines with a Tetrasubstituted Carbon Stereocenter

et al. 2023

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Visible light induced activation of para‐benzoquinone, and its sequential coupling with alkynes and ortho‐phenylenediamines/ortho‐aminophenols is reported. The protocol provides a route for synthesizing value‐added quinoxaline derivatives with tetrasubstituted carbon stereocenter at room temperature in 36–75% yields. Mechanistic investigation suggests that the reaction proceeds via in‐situ generation of para‐quinone methide through direct excitation of para‐benzoquinone in blue light.

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Quinoxaline-Embedded Polyacenoquinone Esters: Synthesis, Electronic Properties, and Crystal Structure

Cited by 11 publications

References 47 publications

Azaacenes Based Electroactive Materials: Preparation, Structure, Electrochemistry, Spectroscopy and Applications—A Critical Review

Azaacenes Based Electroactive Materials: Preparation, Structure, Electrochemistry, Spectroscopy and Applications—A Critical Review

Crystal structures of two 2,3-diethylnaphtho[2,3-g]quinoxaline-6,11-dione derivatives

Photo‐Induced Functionalization of para‐Benzoquinones: Access to Dihydroquinoxalines with a Tetrasubstituted Carbon Stereocenter

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