Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

Baranov, Denis S.; Uvarov, Mikhail N.; Kazantsev, Maxim S.; Mostovich, Evgeny A.; Glebov, Evgeni M.; Gatilov, Yuri V.; Кулик, Л. В.

doi:10.1016/j.dyepig.2016.09.026

Cited by 5 publications

(3 citation statements)

References 40 publications

(17 reference statements)

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“…15,16 1,7-Diazaperylene (1) is accessible on a lab scale in a five step synthesis from 1,5-diaminoanthraquinone and the Meerwein reaction 17,18 with vinylidene chloride; however, the upscaling necessary for its use in a functional material capacity is limited by both the low solubility of intermediates and the need to use a considerable amount of additional Raney nickel as a reducing agent. An alternative synthesis 19 for derivatives of 1 by a ring closure of 1,5-diethynyl derivatives obtained from 1,5-diiodoanthraquinone, 20,21 PdCl 2 , and CuI, and its Sonogashira reaction with alkynes was developed; however, this was still a multi-step synthesis. Moreover, the unsubstituted 1 was not prepared by this route where the handling of the there-fore necessary CuC 2 (CAS RN 12540-13-5) is problematic.…”

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confidence: 99%

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

Langhals¹,

Mayer²,

Polborn³

2020

Synthesis

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confidence: 99%

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

Langhals¹,

Mayer²,

Polborn³

2020

Synthesis

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“…Among them, 1,7‐diazaperylene (benz[de]isoquino[1,8‐gh]quinoline), CAS RN 85903 s97‐5) [2] has been so far the focus of several investigations because of its high fluorescence quantum yield ( i. e . ∼83 %) and substantial chemical and photochemical stability [3–13] . The electron withdrawing effect of the two nitrogen atoms stabilizes chemically the heterocycle compared with the parent hydrocarbon perylene.…”

Section: Introductionmentioning

confidence: 99%

“…[1] Among them, 1,7-diazaperylene (benz[de]isoquino [1,8gh]quinoline), CAS RN 85903 s97-5) [2] has been so far the focus of several investigations because of its high fluorescence quantum yield (i. e. ~83 %) and substantial chemical and photochemical stability. [3][4][5][6][7][8][9][10][11][12][13] The electron withdrawing effect of the two nitrogen atoms stabilizes chemically the heterocycle compared with the parent hydrocarbon perylene. The planarity of 1,7-diazaperylene in contrast to the twisted geometry of the latter allows a more densely packing in solids as is shown by comparing the x-ray crystal structures of the two.…”

Section: Introductionmentioning

confidence: 99%

1,7‐Diazaperylene in Organic Field Effect Transistors

Yumusak

Mayr

Wielend

et al. 2022

Israel Journal of Chemistry

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A thorough material characterization of 1,7-diazaperylene via multiple investigation techniques (cyclic voltammetry, photoluminescence, photoluminescence excitation, impedance spectroscopy) was performed to understand its applicability in organic electronic devices. The recorded data of this perylene derivative was placed in conjunction with the respective data of the parent perylene molecule, and the behavior of this novel compound in organic electronic devices (planar diodes and field effect transistors explained). Although no photovoltaic effect behavior was recorded in planar diodes where 1,7-diazaperylene was employed both as a donor as well as an acceptor, the perylene derivatives proves functional as dielectric layer in organic field effect transistors.

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A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles

et al. 2018

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A concise organolithium‐free route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron‐accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′‐[2,2′‐arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light‐induced electron transfer in their blend with a donor polymer, poly(3‐hexylthiophene‐2,5‐diyl), detected by electron paramagnetic resonance spectroscopy.

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Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

Cited by 5 publications

References 40 publications

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

1,7‐Diazaperylene in Organic Field Effect Transistors

A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles

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