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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Published in: | New journal of chemistry 2024-01, Vol.48 (5), p.1983-1991 |
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Main Authors: | , , , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites |
Online Access: | Get full text |
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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. |
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ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/d3nj05306g |