Synthesis and Physical Chemistry of <i>s</i>‐Tetrazines: Which Ones are Fluorescent and Why?

Gong, Yong-Hua; Miomandre, Fabien; Méallet‐Renault, Rachel; Badré, Sophie; Galmiche, Laurent; Tang, Jie; Audebert, Pierre; Clavier, Gilles

doi:10.1002/ejoc.200900964

Cited by 122 publications

(119 citation statements)

References 39 publications

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“…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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Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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“…[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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“…They have attracted attention of scientists in various fields of research: theoretical chemistry [2], coordination chemistry [3], pharmaceutical chemistry [4], and natural products chemistry [5] amongst others. Research for special applications of this compound class includes anti-corrosion agents [6] and sensors [7,8]. A detailed review of the recent advantages and applications of stetrazine chemistry in general is given by Saracoglu et al [9].…”

Section: Introductionmentioning

confidence: 99%

Thermally Stable 3,6-Disubstituted 1,2,4,5-Tetrazines

Klapötke

Preimesser

Stierstorfer

2013

Zeitschrift Für Naturforschung B

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Several 3,6-disubstituted 1,2,4,5-tetrazines were synthesized by nucleophilic substitution using 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine and 3,6-dichloro-1,2,4,5-tetrazine as electrophiles. All new compounds were characterized by 1 H NMR, 13 C NMR and vibrational spectroscopy, mass spectrometry and elemental analysis (C,H,N). For analysis of the thermostability, differential scanning calorimetry (DSC) was used. Especially, the symmetrically bis-3,5-diamino-1,2,4-triazolyl-substituted derivative shows a very high thermal stability up to 370 • C. Therefore its energetic properties were determined and compared with thoses of hexanitrostilbene (HNS). The crystal structures of 3,6-bishydrazino-1,2,4,5-tetrazine, 3,6-dichloro-1,2,4,5-tetrazine and 3-amino-6-(3,5-diamino-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine dihydrate have been determined by low-temperature X-ray diffraction.

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Synthesis and Physical Chemistry of s‐Tetrazines: Which Ones are Fluorescent and Why?

Cited by 122 publications

References 39 publications

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

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?

Thermally Stable 3,6-Disubstituted 1,2,4,5-Tetrazines

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