Novel helix-shape bis[1,2,4]triazolo[4,3-:3′,4′-][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties

A two-step route to a wide range of new derivatives of 1,8-disubstituted bis[1,2,4]triazolo[4,3- b :3,4- f ][1,2,4,5]tetrazines starting with the readily available 3,6-dihydrazinyl-1,2,4,5-tetrazine and the corresponding aldehydes has been proposed. The developed method is convenient and transition...

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Veröffentlicht in:New journal of chemistry 2024-01, Vol.48 (5), p.1983-1991
Hauptverfasser: Korotina, Anna V, Tolshchina, Svetlana G, Gazizov, Denis A, Steparuk, Alexander S, Kim, Grigory A, Demina, Nadezhda S, Ganebnykh, Ilya N, Slepukhin, Pavel A, Aleksandrov, Alexey E, Tameev, Alexey R, Rusinov, Gennady L
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container_end_page 1991
container_issue 5
container_start_page 1983
container_title New journal of chemistry
container_volume 48
creator Korotina, Anna V
Tolshchina, Svetlana G
Gazizov, Denis A
Steparuk, Alexander S
Kim, Grigory A
Demina, Nadezhda S
Ganebnykh, Ilya N
Slepukhin, Pavel A
Aleksandrov, Alexey E
Tameev, Alexey R
Rusinov, Gennady L
description A two-step route to a wide range of new derivatives of 1,8-disubstituted bis[1,2,4]triazolo[4,3- b :3,4- f ][1,2,4,5]tetrazines starting with the readily available 3,6-dihydrazinyl-1,2,4,5-tetrazine and the corresponding aldehydes has been proposed. The developed method is convenient and transition metal-free. The basic optical, electrochemical and semiconductor properties of the resulting compounds have been studied. The synthesized bis[1,2,4]triazolo[4,3- b :3,4- f ][1,2,4,5]tetrazines show weak luminescent properties in MeCN solution with the highest quantum yields within 21-23%; they have an unexpected quasi-reversible electroreduction peak and exhibit ambipolar semiconductor properties with charge carrier mobilities ranging from 10 −4 to 10 −6 cm 2 V −1 s −1 . The DFT and TDDFT calculations have also been performed to explain the observed features. Synthesis of the bis[1,2,4]triazolo[4,3- b :3,4- f ][1,2,4,5]tetrazines as well as a study of the basic optical, electrochemical and charge-transport properties of new compounds.
doi_str_mv 10.1039/d3nj05306g
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The developed method is convenient and transition metal-free. The basic optical, electrochemical and semiconductor properties of the resulting compounds have been studied. The synthesized bis[1,2,4]triazolo[4,3- b :3,4- f ][1,2,4,5]tetrazines show weak luminescent properties in MeCN solution with the highest quantum yields within 21-23%; they have an unexpected quasi-reversible electroreduction peak and exhibit ambipolar semiconductor properties with charge carrier mobilities ranging from 10 −4 to 10 −6 cm 2 V −1 s −1 . The DFT and TDDFT calculations have also been performed to explain the observed features. 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identifier ISSN: 1144-0546
ispartof New journal of chemistry, 2024-01, Vol.48 (5), p.1983-1991
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1369-9261
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Aldehydes
Charge transfer
Current carriers
Optical properties
Transition metals
title Novel helix-shape bis[1,2,4]triazolo[4,3-:3′,4′-][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties
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