Loading…
Synthesis, Isolation, and Structural Study of Trifluoromethyl Derivatives of the IPR Isomer of C 84 Fullerene, C 84 (11)(CF 3 ) 14,16,18
C 84 is the most abundant higher fullerene which is present in the arc‐discharge fullerene soot. Among 24 topologically possible IPR isomers of C 84 , two major isomers, C 84 (22) and C 84 (23), and several minor ones have been identified experimentally. We report the synthesis, isolation, and struc...
Saved in:
| Published in: | ChemistrySelect (Weinheim) 2022-11, Vol.7 (44) |
|---|---|
| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3 |
| container_end_page | |
| container_issue | 44 |
| container_start_page | |
| container_title | ChemistrySelect (Weinheim) |
| container_volume | 7 |
| creator | Tamm, Nadezhda B. Fritz, Maria A. Romanova, Natalia A. Markov, Vitaliy Yu Goryunkov, Alexey A. Troyanov, Sergey I. |
| description | C
84
is the most abundant higher fullerene which is present in the arc‐discharge fullerene soot. Among 24 topologically possible IPR isomers of C
84
, two major isomers, C
84
(22) and C
84
(23), and several minor ones have been identified experimentally. We report the synthesis, isolation, and structure elucidation of trifluoromethyl derivatives of the most abundant minor isomer of C
84
, C
84
(11)(CF
3
)
14,16,18
. The experimentally determined addition patterns of altogether eight new compounds, four C
84
(11)(CF
3
)
14
, three C
84
(11)(CF
3
)
16
, and one C
84
(11)(CF
3
)
18
, are discussed in terms of the attachments in ribbons of
para
C
6
(CF
3
)
2
hexagons and formation of stabilizing substructures of local aromaticity on the
C
2
−C
84
(11) carbon cage. The general principles of multi addition of bulky CF
3
groups are considered which are based on theoretical DFT calculations of formation energies of C
84
(11)(CF
3
)
n
isomers. Thus, trifluoromethylation pathways are now discussed in details for five different isomers of C
84
. |
| doi_str_mv | 10.1002/slct.202202214 |
| format | article |
| fullrecord | <record><control><sourceid>crossref</sourceid><recordid>TN_cdi_crossref_primary_10_1002_slct_202202214</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1002_slct_202202214</sourcerecordid><originalsourceid>FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3</originalsourceid><addsrcrecordid>eNpNkNFLwzAQxoMoOOZefc7jBu3MJWmaPUq1Ohgobu-lyy6skrWStIP-B_7ZtkxEOLjvvrv7PXyE3ANbAmP8ITjTLjnjY4G8IhMuVBKrRK6u_-lbMgvhkzEGSiuepBPyve3r9oihChFdh8aVbdXUES3rA922vjNt50s3yO7Q08bSna-s6xrfnLA99o4-oa_Ow88Zw7geSHT9_jGSTuhHJ6Na0rxzDj3WGF3mOcBinuVU0AUFGYGKQN-RG1u6gLPfPiXb_HmXvcabt5d19riJjZYyRlQcpZQajC1NylbMMgtpuk9wJcReGuCoDooNZzoBLdjgiRT2oJRkYMSULC9U45sQPNriy1en0vcFsGIMshiDLP6CFD9bkWJN</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis, Isolation, and Structural Study of Trifluoromethyl Derivatives of the IPR Isomer of C 84 Fullerene, C 84 (11)(CF 3 ) 14,16,18</title><source>Wiley-Blackwell Read & Publish Collection</source><creator>Tamm, Nadezhda B. ; Fritz, Maria A. ; Romanova, Natalia A. ; Markov, Vitaliy Yu ; Goryunkov, Alexey A. ; Troyanov, Sergey I.</creator><creatorcontrib>Tamm, Nadezhda B. ; Fritz, Maria A. ; Romanova, Natalia A. ; Markov, Vitaliy Yu ; Goryunkov, Alexey A. ; Troyanov, Sergey I.</creatorcontrib><description>C
84
is the most abundant higher fullerene which is present in the arc‐discharge fullerene soot. Among 24 topologically possible IPR isomers of C
84
, two major isomers, C
84
(22) and C
84
(23), and several minor ones have been identified experimentally. We report the synthesis, isolation, and structure elucidation of trifluoromethyl derivatives of the most abundant minor isomer of C
84
, C
84
(11)(CF
3
)
14,16,18
. The experimentally determined addition patterns of altogether eight new compounds, four C
84
(11)(CF
3
)
14
, three C
84
(11)(CF
3
)
16
, and one C
84
(11)(CF
3
)
18
, are discussed in terms of the attachments in ribbons of
para
C
6
(CF
3
)
2
hexagons and formation of stabilizing substructures of local aromaticity on the
C
2
−C
84
(11) carbon cage. The general principles of multi addition of bulky CF
3
groups are considered which are based on theoretical DFT calculations of formation energies of C
84
(11)(CF
3
)
n
isomers. Thus, trifluoromethylation pathways are now discussed in details for five different isomers of C
84
.</description><identifier>ISSN: 2365-6549</identifier><identifier>EISSN: 2365-6549</identifier><identifier>DOI: 10.1002/slct.202202214</identifier><language>eng</language><ispartof>ChemistrySelect (Weinheim), 2022-11, Vol.7 (44)</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3</citedby><cites>FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3</cites><orcidid>0000-0003-4460-5370 ; 0000-0003-4452-4087 ; 0000-0003-1663-0341</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Tamm, Nadezhda B.</creatorcontrib><creatorcontrib>Fritz, Maria A.</creatorcontrib><creatorcontrib>Romanova, Natalia A.</creatorcontrib><creatorcontrib>Markov, Vitaliy Yu</creatorcontrib><creatorcontrib>Goryunkov, Alexey A.</creatorcontrib><creatorcontrib>Troyanov, Sergey I.</creatorcontrib><title>Synthesis, Isolation, and Structural Study of Trifluoromethyl Derivatives of the IPR Isomer of C 84 Fullerene, C 84 (11)(CF 3 ) 14,16,18</title><title>ChemistrySelect (Weinheim)</title><description>C
84
is the most abundant higher fullerene which is present in the arc‐discharge fullerene soot. Among 24 topologically possible IPR isomers of C
84
, two major isomers, C
84
(22) and C
84
(23), and several minor ones have been identified experimentally. We report the synthesis, isolation, and structure elucidation of trifluoromethyl derivatives of the most abundant minor isomer of C
84
, C
84
(11)(CF
3
)
14,16,18
. The experimentally determined addition patterns of altogether eight new compounds, four C
84
(11)(CF
3
)
14
, three C
84
(11)(CF
3
)
16
, and one C
84
(11)(CF
3
)
18
, are discussed in terms of the attachments in ribbons of
para
C
6
(CF
3
)
2
hexagons and formation of stabilizing substructures of local aromaticity on the
C
2
−C
84
(11) carbon cage. The general principles of multi addition of bulky CF
3
groups are considered which are based on theoretical DFT calculations of formation energies of C
84
(11)(CF
3
)
n
isomers. Thus, trifluoromethylation pathways are now discussed in details for five different isomers of C
84
.</description><issn>2365-6549</issn><issn>2365-6549</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkNFLwzAQxoMoOOZefc7jBu3MJWmaPUq1Ohgobu-lyy6skrWStIP-B_7ZtkxEOLjvvrv7PXyE3ANbAmP8ITjTLjnjY4G8IhMuVBKrRK6u_-lbMgvhkzEGSiuepBPyve3r9oihChFdh8aVbdXUES3rA922vjNt50s3yO7Q08bSna-s6xrfnLA99o4-oa_Ow88Zw7geSHT9_jGSTuhHJ6Na0rxzDj3WGF3mOcBinuVU0AUFGYGKQN-RG1u6gLPfPiXb_HmXvcabt5d19riJjZYyRlQcpZQajC1NylbMMgtpuk9wJcReGuCoDooNZzoBLdjgiRT2oJRkYMSULC9U45sQPNriy1en0vcFsGIMshiDLP6CFD9bkWJN</recordid><startdate>20221125</startdate><enddate>20221125</enddate><creator>Tamm, Nadezhda B.</creator><creator>Fritz, Maria A.</creator><creator>Romanova, Natalia A.</creator><creator>Markov, Vitaliy Yu</creator><creator>Goryunkov, Alexey A.</creator><creator>Troyanov, Sergey I.</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-4460-5370</orcidid><orcidid>https://orcid.org/0000-0003-4452-4087</orcidid><orcidid>https://orcid.org/0000-0003-1663-0341</orcidid></search><sort><creationdate>20221125</creationdate><title>Synthesis, Isolation, and Structural Study of Trifluoromethyl Derivatives of the IPR Isomer of C 84 Fullerene, C 84 (11)(CF 3 ) 14,16,18</title><author>Tamm, Nadezhda B. ; Fritz, Maria A. ; Romanova, Natalia A. ; Markov, Vitaliy Yu ; Goryunkov, Alexey A. ; Troyanov, Sergey I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tamm, Nadezhda B.</creatorcontrib><creatorcontrib>Fritz, Maria A.</creatorcontrib><creatorcontrib>Romanova, Natalia A.</creatorcontrib><creatorcontrib>Markov, Vitaliy Yu</creatorcontrib><creatorcontrib>Goryunkov, Alexey A.</creatorcontrib><creatorcontrib>Troyanov, Sergey I.</creatorcontrib><collection>CrossRef</collection><jtitle>ChemistrySelect (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tamm, Nadezhda B.</au><au>Fritz, Maria A.</au><au>Romanova, Natalia A.</au><au>Markov, Vitaliy Yu</au><au>Goryunkov, Alexey A.</au><au>Troyanov, Sergey I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Isolation, and Structural Study of Trifluoromethyl Derivatives of the IPR Isomer of C 84 Fullerene, C 84 (11)(CF 3 ) 14,16,18</atitle><jtitle>ChemistrySelect (Weinheim)</jtitle><date>2022-11-25</date><risdate>2022</risdate><volume>7</volume><issue>44</issue><issn>2365-6549</issn><eissn>2365-6549</eissn><abstract>C
84
is the most abundant higher fullerene which is present in the arc‐discharge fullerene soot. Among 24 topologically possible IPR isomers of C
84
, two major isomers, C
84
(22) and C
84
(23), and several minor ones have been identified experimentally. We report the synthesis, isolation, and structure elucidation of trifluoromethyl derivatives of the most abundant minor isomer of C
84
, C
84
(11)(CF
3
)
14,16,18
. The experimentally determined addition patterns of altogether eight new compounds, four C
84
(11)(CF
3
)
14
, three C
84
(11)(CF
3
)
16
, and one C
84
(11)(CF
3
)
18
, are discussed in terms of the attachments in ribbons of
para
C
6
(CF
3
)
2
hexagons and formation of stabilizing substructures of local aromaticity on the
C
2
−C
84
(11) carbon cage. The general principles of multi addition of bulky CF
3
groups are considered which are based on theoretical DFT calculations of formation energies of C
84
(11)(CF
3
)
n
isomers. Thus, trifluoromethylation pathways are now discussed in details for five different isomers of C
84
.</abstract><doi>10.1002/slct.202202214</doi><orcidid>https://orcid.org/0000-0003-4460-5370</orcidid><orcidid>https://orcid.org/0000-0003-4452-4087</orcidid><orcidid>https://orcid.org/0000-0003-1663-0341</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2365-6549 |
| ispartof | ChemistrySelect (Weinheim), 2022-11, Vol.7 (44) |
| issn | 2365-6549 2365-6549 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_slct_202202214 |
| source | Wiley-Blackwell Read & Publish Collection |
| title | Synthesis, Isolation, and Structural Study of Trifluoromethyl Derivatives of the IPR Isomer of C 84 Fullerene, C 84 (11)(CF 3 ) 14,16,18 |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T03%3A08%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis,%20Isolation,%20and%20Structural%20Study%20of%20Trifluoromethyl%20Derivatives%20of%20the%20IPR%20Isomer%20of%20C%2084%20Fullerene,%20C%2084%20(11)(CF%203%20)%2014,16,18&rft.jtitle=ChemistrySelect%20(Weinheim)&rft.au=Tamm,%20Nadezhda%20B.&rft.date=2022-11-25&rft.volume=7&rft.issue=44&rft.issn=2365-6549&rft.eissn=2365-6549&rft_id=info:doi/10.1002/slct.202202214&rft_dat=%3Ccrossref%3E10_1002_slct_202202214%3C/crossref%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c844-ee62e44481cfac7090f0f177b5e933b4c12e6d60e628518303b4371b166401c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |