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

Standard

Novel helix-shape bis[1,2,4]triazolo[4,3-b:3′,4′-f][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties. / Korotina, Anna ; Tolshchina, Svetlana ; Gazizov, Denis et al.
In: New Journal of Chemistry, Vol. 48, No. 5, 2024, p. 1983-1991.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{3dcc339d15bf47f09b3a3c7e1a9ae02b,

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

abstract = "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.",

author = "Anna Korotina and Svetlana Tolshchina and Denis Gazizov and Alexander Steparuk and Grigory Kim and Nadezhda Demina and Ilya Ganebnykh and Pavel Slepukhin and Alexey Aleksandrov and Alexey Tameev and Gennady Rusinov",

note = "Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch). The work was carried out with the financial support of the Russian Science Foundation (Project no. 19-13-00234).",

year = "2024",

doi = "10.1039/D3NJ05306G",

language = "English",

volume = "48",

pages = "1983--1991",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "5",

}

RIS

TY - JOUR

T1 - Novel helix-shape bis[1,2,4]triazolo[4,3-b:3′,4′-f][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties

AU - Korotina, Anna

AU - Tolshchina, Svetlana

AU - Gazizov, Denis

AU - Steparuk, Alexander

AU - Kim, Grigory

AU - Demina, Nadezhda

AU - Ganebnykh, Ilya

AU - Slepukhin, Pavel

AU - Aleksandrov, Alexey

AU - Tameev, Alexey

AU - Rusinov, Gennady

N1 - Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch). The work was carried out with the financial support of the Russian Science Foundation (Project no. 19-13-00234).

PY - 2024

Y1 - 2024

N2 - 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.

AB - 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.

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001138698000001

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85182362340

U2 - 10.1039/D3NJ05306G

DO - 10.1039/D3NJ05306G

M3 - Article

VL - 48

SP - 1983

EP - 1991

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 5

ER -

ID: 52350262