Reduction potentials of substituted as-triazines and s-tetrazines in acetonitrile

Troll, T.

doi:10.1016/0013-4686(82)80153-9

Cited by 32 publications

(32 citation statements)

References 20 publications

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“…As is typical for 1,2,4,5-tetrazines [4,5], there is an enormous difference of m ore than 1 V between the potentials of the first and the second reduction step, bm tz-* is reduced only irreversibly at a cathodic peak potential of -2.17 V vs. FeCp2+/°.…”

Section: Ligandsmentioning

confidence: 99%

The New Tetrafunctional π Acceptor Ligand 3,6-Bis(2′-pyrimidyl)-1,2,4,5-tetrazine (bmtz): Diruthenium Complexes of bmtz and of its 1,4-Dihydro Form

Kaim

Fees

1995

Zeitschrift Für Naturforschung B

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Synthesis, physical properties and the coordination with two [Ru(bpy)2]2+ complex frag ments are described for 3,6-bis(2'-pyrimidyl)-l,2,4,5-tetrazine (bmtz), the first compact ligand which offers four equivalent a-diimine chelate sites. Spectroelectrochemistry of intensely blue {(a-bmtz)[Ru(bpy)2]2}"+, n = 4, reveals a very facile reduction (n -3) at -0 .4 0 V vs. FeCp2+/o and a metal oxidation (n = 5) at +1.18 V to a diruthenium (II/III) mixed-valent form which exhibits an intervalence transfer absorption at 1490 nm. The corresponding complex {(M-H2bm tz)[Ru(bpy)2]2}4+ with the 1,4-dihydro form H 2bmtz of the tetrafunctional ligand is oxidized in two steps at 0.58 and 1.07 V vs. FeCp2+/°.

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Section: Ligandsmentioning

confidence: 99%

The New Tetrafunctional π Acceptor Ligand 3,6-Bis(2′-pyrimidyl)-1,2,4,5-tetrazine (bmtz): Diruthenium Complexes of bmtz and of its 1,4-Dihydro Form

Kaim

Fees

1995

Zeitschrift Für Naturforschung B

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“…Tetrazine derivatives represent the most electron-deficient aromatic family [1][2][3] and exhibit interesting semiconducting and opto-electronic properties such as redox reversibility on reduction at low potentials [2][3][4]5 and a characteristic n → π* low energy transition, [5][6][7][8] which can be exploited in the fabrication of OLEDs, 9 OFETs, 10 and solar cells. 11,12 N-type semiconducting properties have been profusely studied either for 3,6-diphenyl-s-tetrazine (Ph 2 Tz, see Chart 1) and other diaryl-s-tetrazines (Ar 2 Tz).…”

Section: Introductionmentioning

confidence: 99%

“…11,12 N-type semiconducting properties have been profusely studied either for 3,6-diphenyl-s-tetrazine (Ph 2 Tz, see Chart 1) and other diaryl-s-tetrazines (Ar 2 Tz). 3,4,7,8,[13][14][15][16][17] An essential drawback of Ar 2 Tz to suitably act as a n-type organic semiconductor concerns the localized character of the Lowest Unoccupied Molecular Orbital (LUMO) which does not allow an easy accommodation of an extra electron (see Figure 1). 8,16,17 In the framework of Marcus theory for charge transfer, typically employed to describe the hopping-like charge transport in molecular crystals at room temperature 18 (vide infra), this situation gives rise to a high electron reorganization energy (λ i ).…”

Section: Introductionmentioning

confidence: 99%

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

et al. 2015

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We theoretically describe in this work the n-type semiconducting behavior of a set of bis(arylene-ethynylene)-s-tetrazines ((ArCC) 2 Tz), by comparing their electronic properties with those of their parent diaryl-s-tetrazines (Ar 2 Tz) after the introduction of ethynylene bridges. The significantly reduced internal reorganization energy for electron transfer is ascribed to an extended delocalization of the LUMO for (ArCC) 2 Tz as opposite to that for Ar 2 Tz, which was described mostly localized on the s-tetrazine ring. The largest electronic coupling and the corresponding electron transfer rates found 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 for bis(phenyl-ethynylene)-s-tetrazine, as well as for some halogenated derivatives, are comparable to those reported for the best performing n-type organic semiconductors materials such as diimides and perylenes. The theoretical mobilities for the studied compounds turn out to be in the range 0.3 -1.3 cm 2 V −1 s −1 , close to values experimentally determined for common n-type organic semiconductors used in real devices. In addition, ohmic contacts can be expected when these compounds are coupled to metallic cathodes such as Na, Ca and Sm. For these reasons, the future application of semiconducting bis(phenyl-ethynylene)-s-tetrazine and its fluorinated and brominated derivatives in optoelectronic devices is envisioned.

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“…redox reversibility on reduction and exhibit low potentials 2,4,5 and also they are coloured due to a n → π* low energy transition. [5][6][7][8] In addition, several tetrazine derivatives are fluorescent in the visible wavelength region, λ max ~ 550-570 nm).…”

Section: Introductionmentioning

confidence: 99%

“…[5][6][7][8] In addition, several tetrazine derivatives are fluorescent in the visible wavelength region, λ max ~ 550-570 nm). [9][10][11] Desirable electronic properties have been described for 3,6-diphenyl-s-tetrazine (Ph 2 Tz, Chart 1) and some other diaryl derivatives 3,4,7,8,12,13 which leads us to consider this family of compounds as suitable candidates for n-type semiconducting materials. A proven strategy to improve the n-type semiconductor properties is by functionalizing with electron-withdrawing substituents, such as F, Cl, Br and CN, since they increase the electron affinity and lower the electron injection barrier.…”

Section: Introductionmentioning

confidence: 99%

Electronic Structure and Charge Transport Properties of a Series of 3,6-(Diphenyl)-s-tetrazine Derivatives: Are They Suitable Candidates for Molecular Electronics?

et al. 2014

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Citation for published item:worlD wF nd qr¡ %D qF nd qrz¡ onD eF nd qrndinoEold¡ nD tFwF nd poxD wFeF nd u(tD hFF nd e£ nsD eF nd welguizoD wF nd pern¡ ndezEq¡ omezD wF @PHIRA 9iletroni struture nd hrge trnsport properties of series of QDTE@diphenylAEsEtetrzine derivtives X re they suitle ndidtes for moleulr eletronisc9D tournl of physil hemistry gFD IIV @RTAF ppF PTRPUEPTRQWF Further information on publisher's website: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.

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Reduction potentials of substituted as-triazines and s-tetrazines in acetonitrile

Cited by 32 publications

References 20 publications

The New Tetrafunctional π Acceptor Ligand 3,6-Bis(2′-pyrimidyl)-1,2,4,5-tetrazine (bmtz): Diruthenium Complexes of bmtz and of its 1,4-Dihydro Form

The New Tetrafunctional π Acceptor Ligand 3,6-Bis(2′-pyrimidyl)-1,2,4,5-tetrazine (bmtz): Diruthenium Complexes of bmtz and of its 1,4-Dihydro Form

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

Electronic Structure and Charge Transport Properties of a Series of 3,6-(Diphenyl)-s-tetrazine Derivatives: Are They Suitable Candidates for Molecular Electronics?

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