The spectroelectrochemical, magnetic, and structural characterization of reduced hexaazatriphenylenehexacarbonitrile, HAT(CN)6

Gallegos, Joseph R.; Francis, Anthony; Ockwig, Nathan W.; Rasmussen, Paul G.; Raptis, Raphael G.; Challen, Paul R.; Ouedraogo, Issouf

doi:10.1016/j.synthmet.2009.05.004

Cited by 13 publications

(18 citation statements)

References 13 publications

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“…The formation of mixed stacks most probably occurs through the sliding of [M(CN) 4 ] 2− anions between the stacked HAT(CN) 6 disks. Such behavior can be supported by the fact that the mutual “antiparallel” orientation of the neighboring HAT(CN) 6 in solid 2 is identical to that observed in the TBA + salt of its anion HAT(CN) 6 .− . A slanted orientation of HAT(CN) 6 molecules should be considered due to possible intermolecular CN−π side contacts, which are characteristic for the crystalline phase of HAT(CN) 6 .…”

Section: Resultsmentioning

confidence: 99%

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)₄]²⁻;[HAT(CN)₆]}_∞ (M=Ni, Pd, Pt) Supramolecular Stacks

Kuzniak-Glanowska

Pinkowicz

Hooper

et al. 2018

Chemistry A European J

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The synthesis, crystal structures, spectroscopic characterization, and comprehensive quantum-chemical calculations for a novel series of anion-π hybrid salts (XPh ) [M(CN) ][HAT(CN) ]⋅3 MeCN (X=P, M=Ni (1), Pd (3), Pt (5); X=As, M=Ni (2), Pd (4), Pt (6); HAT(CN) =1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile) are presented. The systems comprise 1D {[M(CN) ] ;[HAT(CN) ]} stacks, in which the electron-rich metal complexes adjust their orientation to match the electron-deficient areas of HAT(CN) . Electronic charge-transfer interactions along the stacks result in polarization of electron density within HAT(CN) and in perturbations along the {[M(CN) ] ;[HAT(CN) ]} contacts. Electronic structure analysis suggests, for example, a relocation of 0.1-0.2 e per molecule from [M(CN) ] to HAT(CN) and anion-π interaction energies of around -65 kcal mol . A reversible structural single-crystal-to-single-crystal transformation, through desolvation/resolvation processes in the solid state, is also reported and a scheme for the formation of anion-π [M(CN) ] /HAT(CN) adducts in MeCN is proposed.

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Section: Resultsmentioning

confidence: 99%

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)₄]²⁻;[HAT(CN)₆]}_∞ (M=Ni, Pd, Pt) Supramolecular Stacks

Kuzniak-Glanowska

Pinkowicz

Hooper

et al. 2018

Chemistry A European J

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“…The chemical structures of the materials used in this work are shown in Figure . The energy levels were determined by ultraviolet photoemission spectroscopy (UPS) and UV–vis absorption spectroscopy;15, 16 the electron mobilities, measured using the time of flight method,17–20 of HATCN and the ETL materials are summarized in Table 1 . In order to understand the charge generation process of the CGUs composed of p‐HTL/HATCN/n‐ETL, we prepared devices consisting of indium tin oxide (ITO)/8 wt% ReO 3 ‐doped TAPC (30 nm)/HATCN (20 nm)/n‐doped ETLs (20 nm)/15 wt% Rb 2 CO 3 ‐doped B3PYMPM (30 nm)/Al (100 nm).…”

Section: Resultsmentioning

confidence: 99%

The Mechanism of Charge Generation in Charge‐Generation Units Composed of p‐Doped Hole‐Transporting Layer/HATCN/n‐Doped Electron‐Transporting Layers

Lee

et al. 2011

Adv Funct Materials

107

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The rate-limiting step of charge generation in charge-generation units (CGUs) composed of a p-doped hole-transporting layer (p-HTL), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (HATCN) and n-doped electron-transporting layer (n-ETL), where 1,1-bis-(4-bis(4-methyl-phenyl)-amino-phenyl)-cyclohexane (TAPC) was used as the HTL is reported. Energy level alignment determined by the capacitance-voltage (C-V) measurements and the current density-voltage characteristics of the structure clearly show that the electron injection at the HATCN/n-ETL junction limits the charge generation in the CGUs rather than charge generation itself at the p-HTL/HATCN junction. Consequently, the CGUs with 30 mol% Rb 2 CO 3 -doped 4,7-diphenyl-1,10-phenanthroline (BPhen) formed with the HATCN layer generates charges very efficiently and the excess voltage required to generate the current density of ±10 mA cm −2 is around 0.17 V, which is extremely small compared with the literature values reported to date.

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“…In spite of these observations, the magnetic properties of HAT-CN derivatives remain still relatively unexplored. 123 Because of all these features, HAT-CN has found interest for a variety of studies and applications that will be summarized below. Interestingly, it is observed that the coordination mode of HAT-CN exerts a drastic effect on its reduction potentials through the ''normal'' effect of s polarization.…”

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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The spectroelectrochemical, magnetic, and structural characterization of reduced hexaazatriphenylenehexacarbonitrile, HAT(CN)6

Cited by 13 publications

References 13 publications

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)₄]²⁻;[HAT(CN)₆]}_∞ (M=Ni, Pd, Pt) Supramolecular Stacks

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)₄]²⁻;[HAT(CN)₆]}_∞ (M=Ni, Pd, Pt) Supramolecular Stacks

The Mechanism of Charge Generation in Charge‐Generation Units Composed of p‐Doped Hole‐Transporting Layer/HATCN/n‐Doped Electron‐Transporting Layers

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

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The spectroelectrochemical, magnetic, and structural characterization of reduced hexaazatriphenylenehexacarbonitrile, HAT(CN)6

Cited by 13 publications

References 13 publications

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)4]2−;[HAT(CN)6]}∞ (M=Ni, Pd, Pt) Supramolecular Stacks

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)4]2−;[HAT(CN)6]}∞ (M=Ni, Pd, Pt) Supramolecular Stacks

The Mechanism of Charge Generation in Charge‐Generation Units Composed of p‐Doped Hole‐Transporting Layer/HATCN/n‐Doped Electron‐Transporting Layers

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

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Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)₄]²⁻;[HAT(CN)₆]}_∞ (M=Ni, Pd, Pt) Supramolecular Stacks

Molecular Deformation, Charge Flow, and Spongelike Behavior in Anion–π {[M(CN)₄]²⁻;[HAT(CN)₆]}_∞ (M=Ni, Pd, Pt) Supramolecular Stacks