Large-Size Linear and Star-Shaped Dihydropyrazine Fused Pyrazinacenes

Tong, Chenhua; Zhao, Wenjing; Luo, Jiancheng; Mao, Hongying; Chen, Wei; Chan, Hardy Sze On; Chi, Chunyan

doi:10.1021/ol2030839

Cited by 45 publications

(36 citation statements)

References 42 publications

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“…For example, Choi, Xiao, Neguyen, and co‐workers employed the 6,7‐dinitroquinoxaline unit as part of synthetic molecular cavitands for supramolecular host‐guest interaction with several substrates from reactions of DCDNQX and resorcinol derivatives. Furthermore, Tong et al . explored reactions of DCDNQX with o‐ diamines and further transformations to synthesize large linear and star‐shaped aza‐acenes with interesting self‐assembly and the potential for application as organic semiconductors.…”

Section: Methodsmentioning

confidence: 99%

Selective Synthesis of Mono‐ and Disubstituted Quinoxalines via Heteroaromatic Nucleophilic Substitution of 2,3‐Dichloro‐6,7‐dinitroquinoxaline (DCDNQX) with Anilines and Phenols

et al. 2018

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The chemistry of quinoxalines has attracted great attention due to the potential applications of this class of nitrogen‐based heterocycle in many areas. In this paper, heteroaromatic nucleophilic substitution of the quinoxaline substrate 2,3‐dichloro‐6,7‐dinitroquinoxaline (DCDNQX) with anilines and phenols is reported. Reactions using this reagent were proven to proceed under mild and metal‐free conditions for selectively obtaining mono and disubstituted products in good to excellent yields.

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Section: Methodsmentioning

confidence: 99%

Selective Synthesis of Mono‐ and Disubstituted Quinoxalines via Heteroaromatic Nucleophilic Substitution of 2,3‐Dichloro‐6,7‐dinitroquinoxaline (DCDNQX) with Anilines and Phenols

et al. 2018

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“…Chan and Chi et al reported a convenient synthesis of large linear and star‐shaped poly(aza)acenes containing fused pyrazine/dihydropyrazine units by the condensation reaction between the new building block, alkylated dihydrotetraazatetracene 1,2‐diamine 162 , and pyrene tetraones ( 163a , b ) or cyclohexaone ( 118 ) (Scheme ) . These azatriphenylene derivatives were reported for the first time as largest star‐shaped dihydropyrazine fused pyrazinacenes.…”

Section: Synthetic Approaches Towards Azatriphenylene Derivatives:mentioning

confidence: 99%

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

et al. 2018

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This review surveys the most useful strategies for the synthesis of azatriphenylenes. Azatriphenylene derivatives are of considerable interest due to their promising photophysical and coordinating properties and to their presence in the composition of natural products. These scaffolds have shown ability as photoluminescent chemosensors for organic anions and nitroaromatic compounds. The straight‐forward construction of an azatriphenylene moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry and material sciences. These target compounds can also be used as components of (metallo)intercalators (insertors) for biological studies as well as photoluminescent emitters. Here we report a review on the synthesis of these scaffolds employing different strategies such as cyclocondensation reaction, Friedel–Crafts reaction, Westphal condensation reaction, Chichibabin‐type condensation reaction, coupling reaction, intermolecular homocoupling‐cyclotrimerization reaction, cycloaddition reaction, Pomeranz–Fritsch cyclization and intramolecular cyclization reaction. In addition, a brief historical approach has also been discussed. This review will cover the synthetic routes to afford azatriphenylene derivatives broadly including mono‐, di‐, tri‐, tetra, and hexa‐azatriphenylenes. As a consequence, this review will contribute ample and updated information on the synthesis of this class of compounds.

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“…Recently, N-heteroacenes, [7][8][9][10] in which sp 2 N atoms have been used to replace CH groups in the backbone of the parent oligoacene systems, [11][12][13][14] have attracted a lot of attention because they are synthetically challenge to make, interesting for theoretical studies, and have potential appli-cations in organic field effect transistors (OFETs), organic light-emitting diodes (OLEDs), organic phototransistors, memory devices, and photovoltaic cells. In our recent research, we have demonstrated that N-heteroacenes can act as anion sensors through anion-p interactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Sensing Behavior of an N‐heteropentacene

Gao

Zhang

2013

Asian J Org Chem

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An N‐heteropentacene, 1,2,5,6‐tetra(5‐hexylthiophene‐2‐yl)‐hexaazapentacene (4HP), was synthesized through one‐step cyclocondensation reaction. The binding behavior of 4HP toward various cations (Ca2+, Cd2+, Co2+, Cr2+, Cu2+ Fe3+, Hg2+, K+, Li+, Mg2+, Mn2+, Na+, Ni2+, Zn2+, and Pb2) was investigated by UV/vis and fluorescence spectroscopy. 4HP demonstrated a selective and sensitive response towards Cu2+ ion, and the detection limit reached 1.2 μM in N,N‐dimethylformamide solution.

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Large-Size Linear and Star-Shaped Dihydropyrazine Fused Pyrazinacenes

Cited by 45 publications

References 42 publications

Selective Synthesis of Mono‐ and Disubstituted Quinoxalines via Heteroaromatic Nucleophilic Substitution of 2,3‐Dichloro‐6,7‐dinitroquinoxaline (DCDNQX) with Anilines and Phenols

Selective Synthesis of Mono‐ and Disubstituted Quinoxalines via Heteroaromatic Nucleophilic Substitution of 2,3‐Dichloro‐6,7‐dinitroquinoxaline (DCDNQX) with Anilines and Phenols

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

Synthesis, Characterization, and Sensing Behavior of an N‐heteropentacene

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