Synthesis and some reactions of hexaazatriphenylenehexanitrile, a hydrogen-free polyfunctional heterocycle with D3h symmetry

Kanakarajan, K.; Czarnik, Anthony W.

doi:10.1021/jo00376a036

Cited by 78 publications

(53 citation statements)

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“…It can be seen that these compounds are related to peripherally substituted octa(dodecy1)phthalocyanine. The synthesis (Scheme 51) involves the reaction of diketone 43 [202,203] with diaminomalononitrile [204] in refluxing glacial acetic acid to give the dialkyldicyanopyrazine (44 …”

Section: Tetrapyrazinoporphyrazinementioning

confidence: 99%

Synthesis and Structural Features

Cammidge¹,

Bushby²

1998

Handbook of Liquid Crystals

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Section: Tetrapyrazinoporphyrazinementioning

confidence: 99%

Synthesis and Structural Features

Cammidge¹,

Bushby²

1998

Handbook of Liquid Crystals

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“…A secondary product of the reaction is the formation of the triple condensation product, which cannot be completely separated chromatographically (nonetheless, the product is pure enough to be used in the next synthetic step). In a further step, three equivalents of the diamine 10 are condensed in an acidic medium with one equivalent of cyclohexane-1,2,3,4,5,6-hexone octahydrate (4) [44] to yield the target compound tri-HAT (8, 36 %).…”

Section: Methodsmentioning

confidence: 99%

Hexaazatriphenylene (HAT) versus tri‐HAT: The Bigger the Better?

Juárez

Oliva

Ramos

et al. 2011

Chemistry A European J

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A new hexaazatriphenylene (HAT) derivative formed by the fusion of three HAT units has been prepared and its electronic and molecular structures have been fully characterized by optical and vibrational Raman spectroscopy, electrochemistry, solid-state UV and inverse photoemission spectroscopy (UPS and IPES), and by quantum-chemical calculations. A comparative HAT versus tri-HAT study was performed. The fusion of three HAT molecules causes modifications in the optical and electrochemical properties consistent with enhanced π-electron delocalization attained in a bigger planar core. Such combined experimental and theoretical studies are useful to balance chemical design with supramolecular engineering directed to find enhanced characteristics for new organic semiconductor applications.

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“…24,25 The first systematic synthesis of functionalized HAT derivatives was reported in 1985 26 and consisted in the condensation between different a-diketones (5a-i) and hexaaminobenzene (6) (Scheme 2). 29,30 However, in order to obtain this basic HAT, the synthetic route depicted in Scheme 3 requires 15 days of work in contrast with Rogers' method (Scheme 2) 27 with which HAT or other HAT derivatives can be obtained on a multigram scale in less than a week. At that time, the synthesis of hexaaminobenzene involved the reduction of explosive aromatic nitrocompounds with different hidrazynes which prevented the production of 6 on a large scale.…”

Section: A Historical Approachmentioning

confidence: 99%

“…30,119 It is a strong electron-deficient discotic heterocyclic molecule with a deep-lying lowest unoccupied molecular orbital (DL-LUMO) level (B5.1 eV) and therefore a large electron affinity that acts as an electronaccepting unit. HAT-CN, a special case of study 1,4,5,8,9,11-Hexaazatriphenylene hexacarbonitrile, or HAT-CN (IUPAC name: dipyrazino[2,3-f:2 0 ,3 0 -h]quinoxaline-2,3,6,7,10,11hexacarbonitrile, 11, Scheme 3), is a cyanoazacarbon, C 18 N 12 , first reported by Czarnik and co-workers.…”

Section: Nano and Microstructures Built By Self Assemblymentioning

confidence: 99%

Hexaazatriphenylene (HAT) derivatives: from synthesis to molecular design, self-organization and device applications

et al. 2015

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Dipyrazino[2,3-f:2′,3′-h]quinoxaline also known as 1,4,5,8,9,12-hexaazatriphenylene (HAT) is an electron deficient, rigid, planar, aromatic discotic system with an excellent π–π stacking ability. Because it is one of the smallest two-dimensional N-containing polyheterocyclic aromatic systems, it has been used as the basic scaffold for larger 2D N-substituted polyheterocyclic aromatics. Furthermore, it is the building block of choice in a plethora of molecular, macromolecular and supramolecular systems for a variety of applications. This review is aimed to critically review the research performed during the almost three decades of research based on HAT from the synthetic, theoretical and application points of view. The design principles and synthetic strategies towards HAT derivatives will be established and their use in n-type semiconductors, sensors, nonlinear optical chromophores, liquid crystals, microporous polymers for energy storage and nano and microstructures will reveal the relevance of HAT as a basic scaffold in the areas of organic materials and nanoscience.

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Synthesis and some reactions of hexaazatriphenylenehexanitrile, a hydrogen-free polyfunctional heterocycle with D3h symmetry

Cited by 78 publications

References 0 publications

Synthesis and Structural Features

Synthesis and Structural Features

Hexaazatriphenylene (HAT) versus tri‐HAT: The Bigger the Better?

Hexaazatriphenylene (HAT) derivatives: from synthesis to molecular design, self-organization and device applications

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