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 |
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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 |
format | Article |
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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.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d3nj05306g</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aldehydes ; Charge transfer ; Current carriers ; Optical properties ; Transition metals</subject><ispartof>New journal of chemistry, 2024-01, Vol.48 (5), p.1983-1991</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c240t-92bbee795452363329ed952141e3a7f7576ac3f57ed9d3387d8b9216e92a53a43</cites><orcidid>0000-0003-4820-3205 ; 0000-0001-8865-3361 ; 0000-0001-8132-9905 ; 0000-0002-0818-2406 ; 0000-0002-0884-8183 ; 0000-0003-3235-4674 ; 0000-0003-3988-3544</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Korotina, Anna V</creatorcontrib><creatorcontrib>Tolshchina, Svetlana G</creatorcontrib><creatorcontrib>Gazizov, Denis A</creatorcontrib><creatorcontrib>Steparuk, Alexander S</creatorcontrib><creatorcontrib>Kim, Grigory A</creatorcontrib><creatorcontrib>Demina, Nadezhda S</creatorcontrib><creatorcontrib>Ganebnykh, Ilya N</creatorcontrib><creatorcontrib>Slepukhin, Pavel A</creatorcontrib><creatorcontrib>Aleksandrov, Alexey E</creatorcontrib><creatorcontrib>Tameev, Alexey R</creatorcontrib><creatorcontrib>Rusinov, Gennady L</creatorcontrib><title>Novel helix-shape bis[1,2,4]triazolo[4,3-:3′,4′-][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties</title><title>New journal of chemistry</title><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.</description><subject>Aldehydes</subject><subject>Charge transfer</subject><subject>Current carriers</subject><subject>Optical properties</subject><subject>Transition metals</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpFkMFKw0AQhoMoWKsX70LAmyS6u7O76fYmVasi9aKnUsImmTQpMYm7qdh68Zl8JJ_E1YpeZoZ_PuZnfs87pOSUElBnGdQLIoDI-ZbXoyBVqJik226mnIdEcLnr7Vm7IITSSNKe9zZpXrDyC6zK19AWukU_Ke2UBizgs86Uet1UzZQHEA7h8_0j4K6Es80-ELMOO6PXZY126NtV3RVoSxv4TduVqa58XWd-Wmgzx9Bxtc3R-K1pWjRdiXbf28l1ZfHgt_e9x6vLh9F1eHc_vhmd34Up46RzHyQJYqQEFwwkAFOYKcEopwg6yiMRSZ1CLiInZwCDKBskilGJimkBmkPfO97cddbPS7RdvGiWpnaWMVNUAR9ISR11sqFS01hrMI9bUz5ps4opib_DjS9gcvsT7tjBRxvY2PSP-w8fvgCU2naY</recordid><startdate>20240129</startdate><enddate>20240129</enddate><creator>Korotina, Anna V</creator><creator>Tolshchina, Svetlana G</creator><creator>Gazizov, Denis A</creator><creator>Steparuk, Alexander S</creator><creator>Kim, Grigory A</creator><creator>Demina, Nadezhda S</creator><creator>Ganebnykh, Ilya N</creator><creator>Slepukhin, Pavel A</creator><creator>Aleksandrov, Alexey E</creator><creator>Tameev, Alexey R</creator><creator>Rusinov, Gennady L</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-4820-3205</orcidid><orcidid>https://orcid.org/0000-0001-8865-3361</orcidid><orcidid>https://orcid.org/0000-0001-8132-9905</orcidid><orcidid>https://orcid.org/0000-0002-0818-2406</orcidid><orcidid>https://orcid.org/0000-0002-0884-8183</orcidid><orcidid>https://orcid.org/0000-0003-3235-4674</orcidid><orcidid>https://orcid.org/0000-0003-3988-3544</orcidid></search><sort><creationdate>20240129</creationdate><title>Novel helix-shape bis[1,2,4]triazolo[4,3-:3′,4′-][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties</title><author>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</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c240t-92bbee795452363329ed952141e3a7f7576ac3f57ed9d3387d8b9216e92a53a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aldehydes</topic><topic>Charge transfer</topic><topic>Current carriers</topic><topic>Optical properties</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Korotina, Anna V</creatorcontrib><creatorcontrib>Tolshchina, Svetlana G</creatorcontrib><creatorcontrib>Gazizov, Denis A</creatorcontrib><creatorcontrib>Steparuk, Alexander S</creatorcontrib><creatorcontrib>Kim, Grigory A</creatorcontrib><creatorcontrib>Demina, Nadezhda S</creatorcontrib><creatorcontrib>Ganebnykh, Ilya N</creatorcontrib><creatorcontrib>Slepukhin, Pavel A</creatorcontrib><creatorcontrib>Aleksandrov, Alexey E</creatorcontrib><creatorcontrib>Tameev, Alexey R</creatorcontrib><creatorcontrib>Rusinov, Gennady L</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Korotina, Anna V</au><au>Tolshchina, Svetlana G</au><au>Gazizov, Denis A</au><au>Steparuk, Alexander S</au><au>Kim, Grigory A</au><au>Demina, Nadezhda S</au><au>Ganebnykh, Ilya N</au><au>Slepukhin, Pavel A</au><au>Aleksandrov, Alexey E</au><au>Tameev, Alexey R</au><au>Rusinov, Gennady L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel helix-shape bis[1,2,4]triazolo[4,3-:3′,4′-][1,2,4,5]tetrazines: synthesis, optical and charge-transfer properties</atitle><jtitle>New journal of chemistry</jtitle><date>2024-01-29</date><risdate>2024</risdate><volume>48</volume><issue>5</issue><spage>1983</spage><epage>1991</epage><pages>1983-1991</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><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.
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.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d3nj05306g</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-4820-3205</orcidid><orcidid>https://orcid.org/0000-0001-8865-3361</orcidid><orcidid>https://orcid.org/0000-0001-8132-9905</orcidid><orcidid>https://orcid.org/0000-0002-0818-2406</orcidid><orcidid>https://orcid.org/0000-0002-0884-8183</orcidid><orcidid>https://orcid.org/0000-0003-3235-4674</orcidid><orcidid>https://orcid.org/0000-0003-3988-3544</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1144-0546 |
ispartof | New journal of chemistry, 2024-01, Vol.48 (5), p.1983-1991 |
issn | 1144-0546 1369-9261 |
language | eng |
recordid | cdi_proquest_journals_2919348661 |
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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