Derivatives of Octaethynylphenazine and Hexaethynylquinoxaline

Miao, Shaobin; Bangcuyo, Carlito G.; Smith, Mark D.; Bunz, Uwe H. F.

doi:10.1002/ange.200502067

Cited by 10 publications

(4 citation statements)

References 51 publications

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“…Azaacenes have lone pairs of electrons on the sp 2 -hybridized N atoms, which can be protonated, or coordinate with metal ions, or have strong interactions with anions, which make it plausible for rationally designed or modified azaacenes to be used as ion probes. In 2012, Bunz and co-workers synthesized a series of water-soluble bis-triazolylphenazine adducts 36a – d and 37a – d .…”

Section: Applicationsmentioning

confidence: 99%

Linearly Fused Azaacenes: Novel Approaches and New Applications Beyond Field-Effect Transistors (FETs)

Zhang

2015

ACS Appl. Mater. Interfaces

239

132

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Replacing the CH groups in the backbones of acenes with heteroatoms offers scientists greater opportunities to tune their properties, as the type, position, number, and the valence of the introduced heteroatoms have strong effects on the frontier orbital energy levels. When the heteroatoms are nitrogen atoms, all of the resulting materials are called azaacenes. Recently, the synthesis, structure, physical properties, and applications of azaacene derivatives have been intensively investigated. This review focuses on recent synthetic efforts (since 2013) toward making novel azaacenes as well as their potential applications beyond field-effect transistors (FETs) including organic light-emitting diodes (OLEDs), memory devices, phototransistors, solar cells, photoelectrical chemical cells, sensors, and conductors.

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Section: Applicationsmentioning

confidence: 99%

Linearly Fused Azaacenes: Novel Approaches and New Applications Beyond Field-Effect Transistors (FETs)

Zhang

2015

ACS Appl. Mater. Interfaces

239

132

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“…The method developed by Bublitz and co‐workers allows the synthesis of tetrabromo‐2,1,3‐BTD 46 in reasonable yield (53 %) on a multigram scale. Compound 46 was efficiently used in the synthesis of peralkynylated quinoxalines and phenazines 63…”

Section: Synthesis Chemical Properties Sulfur Extrusion and Mismentioning

confidence: 99%

2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

et al. 2012

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2,1,3‐Benzothiadiazole (BTD) is one of the most important nuclei used in the chemistry of photoluminescent compounds and applicable for light technology. The understanding of its properties and reactions is fundamental for the design and application of these derivatives in molecular organic electronic devices and for other technologies. As a result of their potential as constituents of organic light‐emitting diodes, solar cells, liquid crystals, dyes, photovoltaic cells, and many others, attention has been focused on BTD π‐extended derivatives with potential use in this exciting area. Herein, we describe their syntheses, properties, reactions, and selected examples of applications in light technology using by BTD (small molecules) as the core.

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“…[20][21][22] Reaction of 31 with Fausts dione 32 [23] assembles the peralkynylquinoxaline 33, while condensation with tetrabromoorthoquinone followed by a Sonogashira coupling to TIPS-acetylene furnishes octaalkynylphenazine 35 (Scheme 5). [24] A simple variation, that is, the double condensation of 36 with 32 and alkynylation of 37 (Scheme 6), generates pyrazinoquinoxaline 38. [25] The transformation of 37 into 38 was critical, as the formed intermediary diol (from the nucleophilic addition of the lithium acetylide to the quinone functions) could not be reduced by standard methods such as tin dichloride, an apparently general problem when the aromatic body under consideration is electron deficient.…”

Section: Multiply Alkynylated Heterocyclesmentioning

confidence: 99%

N‐Heteroacenes

Bunz

2009

Chemistry A European J

241

108

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The synthesis and the property evaluation of several large N-heteroacenes are discussed. Issues of stability and aromaticity are compared and investigated and a historical perspective of the field is given. Some of the larger heterocyclic materials that are evaluated in this concept article have been around for more than one hundred years, yet their chemistry and properties are not well known/understood.

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Derivatives of Octaethynylphenazine and Hexaethynylquinoxaline

Cited by 10 publications

References 51 publications

Linearly Fused Azaacenes: Novel Approaches and New Applications Beyond Field-Effect Transistors (FETs)

Linearly Fused Azaacenes: Novel Approaches and New Applications Beyond Field-Effect Transistors (FETs)

2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

N‐Heteroacenes

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