2,6,10-Tris(dianisylaminium)-3,7,11- tris(hexyloxy)triphenylene:  A Robust Quartet Molecule at Room Temperature

Fukuzaki, Eiji; Nishide, Hiroyuki

doi:10.1021/ol060379f

Cited by 33 publications

(13 citation statements)

References 44 publications

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“…The magnetization measurements revealed that wT values increased gradually with decreasing temperature and reached its maximum at 40 K, then decreased, indicating the intermolecular antiferromagnetic interaction. 395d The other trifunctional couplers like s-triazine (structure 6.115) 522 or 2,6,10-substituted triphenylene (structure 6.116) 523 have also been studied. The AM1-CI calculation performed for s-triazine by Zhang and Baumgarten 524 suggested that the singlet-triplet splitting is ca.…”

Section: High-spin Macrocyclic Compoundsmentioning

confidence: 99%

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Polymers for electronics and spintronics

et al. 2013

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This critical review is devoted to semiconducting and high spin polymers which are of great scientific interest in view of further development of the organic electronics and the emerging organic spintronic fields. Diversified synthetic strategies are discussed in detail leading to high molecular mass compounds showing appropriate redox (ionization potential (IP), electron affinity (EA)), electronic (charge carrier mobility, conductivity), optoelectronic (electroluminescence, photoconductivity) and magnetic (magnetization, ferromagnetic spin interactions) properties and used as active components of devices such as n- and p-channel field effect transistors, ambipolar light emitting transistors, light emitting diodes, photovoltaic cells, photodiodes, magnetic photoswitches, etc. Solution processing procedures developed with the goal of depositing highly ordered and oriented films of these polymers are also described. This is completed by the description of principal methods that are used for characterizing these macromolecular compounds both in solution and in the solid state. These involve various spectroscopic methods (UV-vis-NIR, UPS, pulse EPR), electrochemistry and spectroelectrochemistry, magnetic measurements (SQUID), and structural and morphological investigations (X-ray diffraction, STM, AFM). Finally, four classes of polymers are discussed in detail with special emphasis on the results obtained in the past three years: (i) high IP, (ii) high |EA|, (iii) low band gap and (iv) high spin ones.

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Section: High-spin Macrocyclic Compoundsmentioning

confidence: 99%

“…Triphenylene was also studied as a ferromagnetic coupler (structure 6.116). 523 It forms planar p-conjugated structure. The size of such a coupler reduces the steric hindrance between substituted arylamine groups and, on the other hand, diminishes the electrostatic repulsion between adjacent radical cations.…”

Section: High-spin Macrocyclic Compoundsmentioning

confidence: 99%

Polymers for electronics and spintronics

et al. 2013

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“…Indeed, their synthesis is shorter and more direct than that of their bromo‐TP homologs, as they can be obtained directly in one‐step from the corresponding and readily available hydroxytriphenylenes by reaction with triflic anhydride . Triphenylenyl triflates and nonaflates have been used for C–N and C–C bond construction, respectively, in functional material synthesis. In this context, TP triflate derivatives would seem to be more useful and relevant starting materials for the synthesis of mixed alkoxy/aryltriphenylenes.…”

Section: Introductionmentioning

confidence: 99%

Discogens Possessing Aryl Side Groups Synthesized by Suzuki Coupling of Triphenylene Triflates and Their Self‐Organization Behavior

Zhao

Gao

et al. 2016

Eur J Org Chem

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Pd‐catalyzed Suzuki cross‐coupling reactions between arylboronic acids and bromoarenes have been applied widely in the synthesis of liquid‐crystalline materials. However, aryl triflate derivatives have been less used despite their high chemical tolerance, reactivity, and chemical accessibility. In this report, three series of discogens have been synthesized in good yields from appropriate triphenylene triflate precursors by Suzuki coupling reactions with various commercial arylboronic acids (e.g., aryl = phenylene, thiophene, naphthalene, triarylamine, carbazole, and fluorene). The synthesized discogens display broad mesophase ranges and high thermal stabilities. Moreover, those bearing triarylamine, carbazole, and fluorene side groups are also blue‐light emitters. The availability of the triflate precursors coupled with their highly efficient cross‐coupling with commercial arylboronic acids make this strategy extremely versatile and attractive for the design of new functional materials.

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“…Our recent examples include triarylamine-based high-spin oligo-and poly(cationic radical)s, [36][37][38][39][40][41] polymer gels of p-phenylenediamine-based cationic radicals, 42 as well as their applications to organic devices. 43,44 During the course of this series of studies, we have shown an RT ground state multiplet polyradical using a poly[1,2,(4)-phenylenevinyleneanisylaminium] hyperbranched structure, prepared by a tedious multistep synthesis of the AB2-type monomer, followed by self-polycondensation and terminal protection.…”

Section: Introductionmentioning

confidence: 99%

Two-dimensionally extended organic high-spin poly(aminium cationic radical)s and their magnetic force microscopic images

Michinobu

Inui

Nishide

2010

Polym J

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Purely organic high-spin poly(aminium cationic radical)s of two-dimensionally extended soluble aromatic polyamines P1 and P2 were prepared by the palladium-catalyzed polycondensation of two multifunctional monomers, followed by chemical or electrochemical oxidations. The chemical structures of the precursor polyamines were fully characterized by 1 H-and 13 C nuclear magnetic resonance (NMR), infrared and MALDI-TOF mass spectra (MS). The aminium radical sites of N,N,N¢,N¢-tetraaryl-pphenylenediamines were connected through the m-phenylene ferromagnetic coupler, which satisfies the non-Kekulé -type molecular design. Oxidation of radical sites was facilitated by electron-donating methoxy substituents. The first oxidation potential (E o ¢(1)) of P2 with methoxy substituents, evaluated from the cyclic voltammograms in CH 2 Cl 2 , was 0.69 V (vs Ag/Ag + ), whereas the E o ¢(1) of P1 without electron-donating substituents was 0.78 V. This result was further verified by spectroelectrochemistry measurements. The electrochemically oxidized P2 displayed a more intense low-energy band at ca. 800 nm ascribed to aminium cationic radicals and bications. Chemical oxidation of P1 and P2 with NOPF 6 solubilized with 18-crown-6 in CH 2 Cl 2 gave the corresponding poly(aminium cationic radical)s. The high-spin ground states were confirmed by the temperature dependence of forbidden electron spin resonance (ESR) transition peak intensities, and the average spin quantum number (S) determined by the magnetic curves reached 8.4/2 at low temperatures. Remarkably, when a small amount of trifluoroacetic acid was added, the half-life of polyradicals reached ca. 1 week at room temperature (RT). This result prompted us to observe the single polymer-based molecular and magnetic images by atomic force microscopy and magnetic force microscopy, respectively. The precursor polyamine P1 showed globular-shaped polymer particles with an average vertical distance of 1.43 nm. After chemical oxidation, the vertical distance of P1 definitely decreased, reflecting the improved p-type character of the nitrogen atoms. Moreover, the detection of weak MFM images supported the presence of magnetic spins in the single polymers.

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2,6,10-Tris(dianisylaminium)-3,7,11- tris(hexyloxy)triphenylene: A Robust Quartet Molecule at Room Temperature

Cited by 33 publications

References 44 publications

Polymers for electronics and spintronics

Polymers for electronics and spintronics

Discogens Possessing Aryl Side Groups Synthesized by Suzuki Coupling of Triphenylene Triflates and Their Self‐Organization Behavior

Two-dimensionally extended organic high-spin poly(aminium cationic radical)s and their magnetic force microscopic images

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