Boron calixphyrin complexes: exploring the coordination chemistry of a BODIPY/porphyrin hybrid
Boron complexes of calix[4]phyrins (1.1.1.1) were prepared by reacting the free-base ligands with BF ·Et O. The reaction conditions can be efficiently tailored to produce mono- or di-boron calixphyrins. Mono-BF calixphyrins with boron coordinating to either the dipyrrin, BF [H(Calix)], or dipyrromet...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2018, Vol.47 (10), p.3388-3399 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Tay, Aaron Chin Yit Frogley, Benjamin J Ware, David C Brothers, Penelope J |
| description | Boron complexes of calix[4]phyrins (1.1.1.1) were prepared by reacting the free-base ligands with BF
·Et
O. The reaction conditions can be efficiently tailored to produce mono- or di-boron calixphyrins. Mono-BF
calixphyrins with boron coordinating to either the dipyrrin, BF
[H(Calix)], or dipyrromethane, BF
[H(Calix)] and BF
[H
(Calix)]
, bonding sites were isolated. The dipyrromethane isomer, BF
[H(Calix)], isomerises into BF
[H(Calix)] which kinetic studies and DFT calculations indicate is an intramolecular process. Two isomers of B
OF
(Calix) were isolated, one isomer bonding via the dipyrrin sites with the FBOBF moiety in cisoid geometry, and the second isomer bonding via the dipyrromethane sites with the FBOBF moiety in transoid geometry. Although the cisoid/dipyrrin isomer was calculated to be most energetically favourable for B
OF
(Calix), the isolation of the transoid/dipyrromethane isomer is postulated to occur via the presumed intermediate (BF
)
(Calix), for which DFT indicated a preference for transoid/dipyrromethane geometry. |
| doi_str_mv | 10.1039/c7dt04575a |
| format | Article |
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·Et
O. The reaction conditions can be efficiently tailored to produce mono- or di-boron calixphyrins. Mono-BF
calixphyrins with boron coordinating to either the dipyrrin, BF
[H(Calix)], or dipyrromethane, BF
[H(Calix)] and BF
[H
(Calix)]
, bonding sites were isolated. The dipyrromethane isomer, BF
[H(Calix)], isomerises into BF
[H(Calix)] which kinetic studies and DFT calculations indicate is an intramolecular process. Two isomers of B
OF
(Calix) were isolated, one isomer bonding via the dipyrrin sites with the FBOBF moiety in cisoid geometry, and the second isomer bonding via the dipyrromethane sites with the FBOBF moiety in transoid geometry. Although the cisoid/dipyrrin isomer was calculated to be most energetically favourable for B
OF
(Calix), the isolation of the transoid/dipyrromethane isomer is postulated to occur via the presumed intermediate (BF
)
(Calix), for which DFT indicated a preference for transoid/dipyrromethane geometry.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c7dt04575a</identifier><identifier>PMID: 29431798</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Boron ; Chemical bonds ; Coordination compounds ; Geometry ; Isomers ; Mathematical analysis</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2018, Vol.47 (10), p.3388-3399</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-3a220d7e1803e3d6ec920f7279f42dc40ee13031e839dbc5f992f625677e4d2f3</citedby><cites>FETCH-LOGICAL-c381t-3a220d7e1803e3d6ec920f7279f42dc40ee13031e839dbc5f992f625677e4d2f3</cites><orcidid>0000-0002-7199-5362 ; 0000-0002-5406-0653 ; 0000-0001-8350-2361 ; 0000-0002-5405-9193</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4009,27902,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29431798$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tay, Aaron Chin Yit</creatorcontrib><creatorcontrib>Frogley, Benjamin J</creatorcontrib><creatorcontrib>Ware, David C</creatorcontrib><creatorcontrib>Brothers, Penelope J</creatorcontrib><title>Boron calixphyrin complexes: exploring the coordination chemistry of a BODIPY/porphyrin hybrid</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Boron complexes of calix[4]phyrins (1.1.1.1) were prepared by reacting the free-base ligands with BF
·Et
O. The reaction conditions can be efficiently tailored to produce mono- or di-boron calixphyrins. Mono-BF
calixphyrins with boron coordinating to either the dipyrrin, BF
[H(Calix)], or dipyrromethane, BF
[H(Calix)] and BF
[H
(Calix)]
, bonding sites were isolated. The dipyrromethane isomer, BF
[H(Calix)], isomerises into BF
[H(Calix)] which kinetic studies and DFT calculations indicate is an intramolecular process. Two isomers of B
OF
(Calix) were isolated, one isomer bonding via the dipyrrin sites with the FBOBF moiety in cisoid geometry, and the second isomer bonding via the dipyrromethane sites with the FBOBF moiety in transoid geometry. Although the cisoid/dipyrrin isomer was calculated to be most energetically favourable for B
OF
(Calix), the isolation of the transoid/dipyrromethane isomer is postulated to occur via the presumed intermediate (BF
)
(Calix), for which DFT indicated a preference for transoid/dipyrromethane geometry.</description><subject>Boron</subject><subject>Chemical bonds</subject><subject>Coordination compounds</subject><subject>Geometry</subject><subject>Isomers</subject><subject>Mathematical analysis</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkEtLw0AUhQdRbK1u_AEScCNC7LySybjrw0ehUBd14caQZm5MStKJMwk0_96prV24uod7v3s4HISuCX4gmMlhKlSDeSCC5AT1CRfCl5Tx06OmYQ9dWLvGmFIc0HPUo5IzImTUR59jbfTGS5Oy2NZ5ZwqndVWXsAX76MG2LrXbfXlNDu6gjSo2SVPsPnKoCtuYztOZl3jjxXT29jGstTm45N3KFOoSnWVJaeHqMAfo_flpOXn154uX2WQ091MWkcZniUumBJAIM2AqhFRSnAkqZMapSjkGIAwzAhGTapUGmZQ0C2kQCgFc0YwN0N3etzb6uwXbxC5cCmWZbEC3NqYYE45DKrBDb_-ha92ajUvnKEKwIJEQjrrfU6nR1hrI4toUVWK6mOB413o8EdPlb-sjB98cLNtVBeqI_tXMfgA8tnyM</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Tay, Aaron Chin Yit</creator><creator>Frogley, Benjamin J</creator><creator>Ware, David C</creator><creator>Brothers, Penelope J</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7199-5362</orcidid><orcidid>https://orcid.org/0000-0002-5406-0653</orcidid><orcidid>https://orcid.org/0000-0001-8350-2361</orcidid><orcidid>https://orcid.org/0000-0002-5405-9193</orcidid></search><sort><creationdate>2018</creationdate><title>Boron calixphyrin complexes: exploring the coordination chemistry of a BODIPY/porphyrin hybrid</title><author>Tay, Aaron Chin Yit ; Frogley, Benjamin J ; Ware, David C ; Brothers, Penelope J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-3a220d7e1803e3d6ec920f7279f42dc40ee13031e839dbc5f992f625677e4d2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Boron</topic><topic>Chemical bonds</topic><topic>Coordination compounds</topic><topic>Geometry</topic><topic>Isomers</topic><topic>Mathematical analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tay, Aaron Chin Yit</creatorcontrib><creatorcontrib>Frogley, Benjamin J</creatorcontrib><creatorcontrib>Ware, David C</creatorcontrib><creatorcontrib>Brothers, Penelope J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tay, Aaron Chin Yit</au><au>Frogley, Benjamin J</au><au>Ware, David C</au><au>Brothers, Penelope J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Boron calixphyrin complexes: exploring the coordination chemistry of a BODIPY/porphyrin hybrid</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2018</date><risdate>2018</risdate><volume>47</volume><issue>10</issue><spage>3388</spage><epage>3399</epage><pages>3388-3399</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Boron complexes of calix[4]phyrins (1.1.1.1) were prepared by reacting the free-base ligands with BF
·Et
O. The reaction conditions can be efficiently tailored to produce mono- or di-boron calixphyrins. Mono-BF
calixphyrins with boron coordinating to either the dipyrrin, BF
[H(Calix)], or dipyrromethane, BF
[H(Calix)] and BF
[H
(Calix)]
, bonding sites were isolated. The dipyrromethane isomer, BF
[H(Calix)], isomerises into BF
[H(Calix)] which kinetic studies and DFT calculations indicate is an intramolecular process. Two isomers of B
OF
(Calix) were isolated, one isomer bonding via the dipyrrin sites with the FBOBF moiety in cisoid geometry, and the second isomer bonding via the dipyrromethane sites with the FBOBF moiety in transoid geometry. Although the cisoid/dipyrrin isomer was calculated to be most energetically favourable for B
OF
(Calix), the isolation of the transoid/dipyrromethane isomer is postulated to occur via the presumed intermediate (BF
)
(Calix), for which DFT indicated a preference for transoid/dipyrromethane geometry.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29431798</pmid><doi>10.1039/c7dt04575a</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-7199-5362</orcidid><orcidid>https://orcid.org/0000-0002-5406-0653</orcidid><orcidid>https://orcid.org/0000-0001-8350-2361</orcidid><orcidid>https://orcid.org/0000-0002-5405-9193</orcidid></addata></record> |
| fulltext | fulltext |
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| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2018, Vol.47 (10), p.3388-3399 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2001406270 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Boron Chemical bonds Coordination compounds Geometry Isomers Mathematical analysis |
| title | Boron calixphyrin complexes: exploring the coordination chemistry of a BODIPY/porphyrin hybrid |
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