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...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2024-01, Vol.48 (5), p.1983-1991
Main Authors: 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
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj05306g