Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferrocenes
Aryl-substituted sodium 1,2-diphosphacyclopentadienides Na(P 2 C 3 R 3 ) (R = Ph, 4-Me-C 6 H 4 , 4-Cl-C 6 H 4 )( 1a-c ) react with [FeCp(η 6 -C 6 H 5 CH 3 )][PF 6 ] to give heteroleptic 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η 5 -P 2 C 3 R 3 )] ( 2a-c ) in 71-78% yield. The structures of 2a-c w...
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| Veröffentlicht in: | Inorganic chemistry frontiers 2022-05, Vol.9 (11), p.268-2616 |
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| creator | Bezkishko, Ilya A Zagidullin, Almaz A Khrizanforov, Mikhail N Gerasimova, Tatiana P Ivshin, Kamil A Kataeva, Olga N Ganushevich, Yulia S Miluykov, Vasili A Lönnecke, Peter Hey-Hawkins, Evamarie |
| description | Aryl-substituted sodium 1,2-diphosphacyclopentadienides Na(P
2
C
3
R
3
) (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
)(
1a-c
) react with [FeCp(η
6
-C
6
H
5
CH
3
)][PF
6
] to give heteroleptic 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] (
2a-c
) in 71-78% yield. The structures of
2a-c
were confirmed by NMR, UV-Vis spectroscopy and X-ray structure analysis, and supported by DFT calculations. Electrochemical studies of
2a-c
in CH
3
CN demonstrate a pronounced reversible one-electron oxidation, while in the solid state, all 3,4,5-triaryl-1,2-diphosphaferrocenes show fully reversible oxidation and reduction waves, which indicates the stability of the oxidized form. Regardless of the substituent (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
), the studied 1,2-diphosphaferrocenes have similar oxidation and reduction potentials.
New 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] have been extensively studied experimentally (NMR, UV-Vis, electrochemical studies, X-ray) and quantum chemically. |
| doi_str_mv | 10.1039/d2qi00446a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_rsc_primary_d2qi00446a</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2671567407</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-97f64fa4778450d39178f1e9abedfb233757a368b99e7b95c11b7d2e6c6d13b13</originalsourceid><addsrcrecordid>eNpNkE1Lw0AQhoMoWGov3oWAN0l0Zz-TY6mfUBBRb0LYbGZJSpqku5tD_73RinqaOTzvzMsTRedAroGw_Kaiu4YQzqU-imaUCJqCEOz4334aLbzfEEIAOAFJZtHH674LNfrGJ7EPbjRhdBjrroqxRRNcb2rcNka38eD6AV1o0Me9jVnCE5EG12i3b1NIaFo1Q937odYW3RTDDv1ZdGJ163HxM-fR-_3d2-oxXT8_PK2W69TQDEKaKyu51VypjAtSsRxUZgFzXWJlS8qYEkozmZV5jqrMhQEoVUVRGlkBK4HNo8vD3anjbkQfik0_um56WVCpQEjFiZqoqwNlXO-9Q1sMrtlO_QsgxZfA4pa-PH0LXE7wxQF23vxyf4LZJx0YbGA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2671567407</pqid></control><display><type>article</type><title>Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferrocenes</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Bezkishko, Ilya A ; Zagidullin, Almaz A ; Khrizanforov, Mikhail N ; Gerasimova, Tatiana P ; Ivshin, Kamil A ; Kataeva, Olga N ; Ganushevich, Yulia S ; Miluykov, Vasili A ; Lönnecke, Peter ; Hey-Hawkins, Evamarie</creator><creatorcontrib>Bezkishko, Ilya A ; Zagidullin, Almaz A ; Khrizanforov, Mikhail N ; Gerasimova, Tatiana P ; Ivshin, Kamil A ; Kataeva, Olga N ; Ganushevich, Yulia S ; Miluykov, Vasili A ; Lönnecke, Peter ; Hey-Hawkins, Evamarie</creatorcontrib><description>Aryl-substituted sodium 1,2-diphosphacyclopentadienides Na(P
2
C
3
R
3
) (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
)(
1a-c
) react with [FeCp(η
6
-C
6
H
5
CH
3
)][PF
6
] to give heteroleptic 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] (
2a-c
) in 71-78% yield. The structures of
2a-c
were confirmed by NMR, UV-Vis spectroscopy and X-ray structure analysis, and supported by DFT calculations. Electrochemical studies of
2a-c
in CH
3
CN demonstrate a pronounced reversible one-electron oxidation, while in the solid state, all 3,4,5-triaryl-1,2-diphosphaferrocenes show fully reversible oxidation and reduction waves, which indicates the stability of the oxidized form. Regardless of the substituent (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
), the studied 1,2-diphosphaferrocenes have similar oxidation and reduction potentials.
New 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] have been extensively studied experimentally (NMR, UV-Vis, electrochemical studies, X-ray) and quantum chemically.</description><identifier>ISSN: 2052-1553</identifier><identifier>ISSN: 2052-1545</identifier><identifier>EISSN: 2052-1553</identifier><identifier>DOI: 10.1039/d2qi00446a</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Electrochemical analysis ; Inorganic chemistry ; NMR ; Nuclear magnetic resonance ; Oxidation ; Reduction ; Sodium ; Structural analysis</subject><ispartof>Inorganic chemistry frontiers, 2022-05, Vol.9 (11), p.268-2616</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-97f64fa4778450d39178f1e9abedfb233757a368b99e7b95c11b7d2e6c6d13b13</citedby><cites>FETCH-LOGICAL-c281t-97f64fa4778450d39178f1e9abedfb233757a368b99e7b95c11b7d2e6c6d13b13</cites><orcidid>0000-0003-3125-7506 ; 0000-0001-8473-5327 ; 0000-0002-9763-5947 ; 0000-0003-1335-0897 ; 0000-0003-4267-0603 ; 0000-0003-4714-4143</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Bezkishko, Ilya A</creatorcontrib><creatorcontrib>Zagidullin, Almaz A</creatorcontrib><creatorcontrib>Khrizanforov, Mikhail N</creatorcontrib><creatorcontrib>Gerasimova, Tatiana P</creatorcontrib><creatorcontrib>Ivshin, Kamil A</creatorcontrib><creatorcontrib>Kataeva, Olga N</creatorcontrib><creatorcontrib>Ganushevich, Yulia S</creatorcontrib><creatorcontrib>Miluykov, Vasili A</creatorcontrib><creatorcontrib>Lönnecke, Peter</creatorcontrib><creatorcontrib>Hey-Hawkins, Evamarie</creatorcontrib><title>Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferrocenes</title><title>Inorganic chemistry frontiers</title><description>Aryl-substituted sodium 1,2-diphosphacyclopentadienides Na(P
2
C
3
R
3
) (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
)(
1a-c
) react with [FeCp(η
6
-C
6
H
5
CH
3
)][PF
6
] to give heteroleptic 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] (
2a-c
) in 71-78% yield. The structures of
2a-c
were confirmed by NMR, UV-Vis spectroscopy and X-ray structure analysis, and supported by DFT calculations. Electrochemical studies of
2a-c
in CH
3
CN demonstrate a pronounced reversible one-electron oxidation, while in the solid state, all 3,4,5-triaryl-1,2-diphosphaferrocenes show fully reversible oxidation and reduction waves, which indicates the stability of the oxidized form. Regardless of the substituent (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
), the studied 1,2-diphosphaferrocenes have similar oxidation and reduction potentials.
New 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] have been extensively studied experimentally (NMR, UV-Vis, electrochemical studies, X-ray) and quantum chemically.</description><subject>Electrochemical analysis</subject><subject>Inorganic chemistry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxidation</subject><subject>Reduction</subject><subject>Sodium</subject><subject>Structural analysis</subject><issn>2052-1553</issn><issn>2052-1545</issn><issn>2052-1553</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkE1Lw0AQhoMoWGov3oWAN0l0Zz-TY6mfUBBRb0LYbGZJSpqku5tD_73RinqaOTzvzMsTRedAroGw_Kaiu4YQzqU-imaUCJqCEOz4334aLbzfEEIAOAFJZtHH674LNfrGJ7EPbjRhdBjrroqxRRNcb2rcNka38eD6AV1o0Me9jVnCE5EG12i3b1NIaFo1Q937odYW3RTDDv1ZdGJ163HxM-fR-_3d2-oxXT8_PK2W69TQDEKaKyu51VypjAtSsRxUZgFzXWJlS8qYEkozmZV5jqrMhQEoVUVRGlkBK4HNo8vD3anjbkQfik0_um56WVCpQEjFiZqoqwNlXO-9Q1sMrtlO_QsgxZfA4pa-PH0LXE7wxQF23vxyf4LZJx0YbGA</recordid><startdate>20220531</startdate><enddate>20220531</enddate><creator>Bezkishko, Ilya A</creator><creator>Zagidullin, Almaz A</creator><creator>Khrizanforov, Mikhail N</creator><creator>Gerasimova, Tatiana P</creator><creator>Ivshin, Kamil A</creator><creator>Kataeva, Olga N</creator><creator>Ganushevich, Yulia S</creator><creator>Miluykov, Vasili A</creator><creator>Lönnecke, Peter</creator><creator>Hey-Hawkins, Evamarie</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0003-3125-7506</orcidid><orcidid>https://orcid.org/0000-0001-8473-5327</orcidid><orcidid>https://orcid.org/0000-0002-9763-5947</orcidid><orcidid>https://orcid.org/0000-0003-1335-0897</orcidid><orcidid>https://orcid.org/0000-0003-4267-0603</orcidid><orcidid>https://orcid.org/0000-0003-4714-4143</orcidid></search><sort><creationdate>20220531</creationdate><title>Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferrocenes</title><author>Bezkishko, Ilya A ; Zagidullin, Almaz A ; Khrizanforov, Mikhail N ; Gerasimova, Tatiana P ; Ivshin, Kamil A ; Kataeva, Olga N ; Ganushevich, Yulia S ; Miluykov, Vasili A ; Lönnecke, Peter ; Hey-Hawkins, Evamarie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-97f64fa4778450d39178f1e9abedfb233757a368b99e7b95c11b7d2e6c6d13b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Electrochemical analysis</topic><topic>Inorganic chemistry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxidation</topic><topic>Reduction</topic><topic>Sodium</topic><topic>Structural analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bezkishko, Ilya A</creatorcontrib><creatorcontrib>Zagidullin, Almaz A</creatorcontrib><creatorcontrib>Khrizanforov, Mikhail N</creatorcontrib><creatorcontrib>Gerasimova, Tatiana P</creatorcontrib><creatorcontrib>Ivshin, Kamil A</creatorcontrib><creatorcontrib>Kataeva, Olga N</creatorcontrib><creatorcontrib>Ganushevich, Yulia S</creatorcontrib><creatorcontrib>Miluykov, Vasili A</creatorcontrib><creatorcontrib>Lönnecke, Peter</creatorcontrib><creatorcontrib>Hey-Hawkins, Evamarie</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Inorganic chemistry frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bezkishko, Ilya A</au><au>Zagidullin, Almaz A</au><au>Khrizanforov, Mikhail N</au><au>Gerasimova, Tatiana P</au><au>Ivshin, Kamil A</au><au>Kataeva, Olga N</au><au>Ganushevich, Yulia S</au><au>Miluykov, Vasili A</au><au>Lönnecke, Peter</au><au>Hey-Hawkins, Evamarie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferrocenes</atitle><jtitle>Inorganic chemistry frontiers</jtitle><date>2022-05-31</date><risdate>2022</risdate><volume>9</volume><issue>11</issue><spage>268</spage><epage>2616</epage><pages>268-2616</pages><issn>2052-1553</issn><issn>2052-1545</issn><eissn>2052-1553</eissn><abstract>Aryl-substituted sodium 1,2-diphosphacyclopentadienides Na(P
2
C
3
R
3
) (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
)(
1a-c
) react with [FeCp(η
6
-C
6
H
5
CH
3
)][PF
6
] to give heteroleptic 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] (
2a-c
) in 71-78% yield. The structures of
2a-c
were confirmed by NMR, UV-Vis spectroscopy and X-ray structure analysis, and supported by DFT calculations. Electrochemical studies of
2a-c
in CH
3
CN demonstrate a pronounced reversible one-electron oxidation, while in the solid state, all 3,4,5-triaryl-1,2-diphosphaferrocenes show fully reversible oxidation and reduction waves, which indicates the stability of the oxidized form. Regardless of the substituent (R = Ph, 4-Me-C
6
H
4
, 4-Cl-C
6
H
4
), the studied 1,2-diphosphaferrocenes have similar oxidation and reduction potentials.
New 3,4,5-triaryl-1,2-diphosphaferrocenes [FeCp(η
5
-P
2
C
3
R
3
)] have been extensively studied experimentally (NMR, UV-Vis, electrochemical studies, X-ray) and quantum chemically.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2qi00446a</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-3125-7506</orcidid><orcidid>https://orcid.org/0000-0001-8473-5327</orcidid><orcidid>https://orcid.org/0000-0002-9763-5947</orcidid><orcidid>https://orcid.org/0000-0003-1335-0897</orcidid><orcidid>https://orcid.org/0000-0003-4267-0603</orcidid><orcidid>https://orcid.org/0000-0003-4714-4143</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-1553 |
| ispartof | Inorganic chemistry frontiers, 2022-05, Vol.9 (11), p.268-2616 |
| issn | 2052-1553 2052-1545 2052-1553 |
| language | eng |
| recordid | cdi_rsc_primary_d2qi00446a |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Electrochemical analysis Inorganic chemistry NMR Nuclear magnetic resonance Oxidation Reduction Sodium Structural analysis |
| title | Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferrocenes |
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