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Synthesis of Five-Porphyrin Nanorings by Using Ferrocene and Corannulene Templates
The smallest and most strained member of a family of π‐conjugated cyclic porphyrin oligomers was synthesized by using pentapyridyl templates based on ferrocene and corannulene. Both templates are effective for directing the synthesis of the butadiyne‐linked cyclic pentamer, despite the fact that the...
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| Published in: | Angewandte Chemie 2016-07, Vol.128 (29), p.8498-8502 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3679-8128f41b600bdfb8f2c131700faf332e52b9cbe919dc650b40eb67d177b5dd013 |
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| cites | cdi_FETCH-LOGICAL-c3679-8128f41b600bdfb8f2c131700faf332e52b9cbe919dc650b40eb67d177b5dd013 |
| container_end_page | 8502 |
| container_issue | 29 |
| container_start_page | 8498 |
| container_title | Angewandte Chemie |
| container_volume | 128 |
| creator | Liu, Pengpeng Hisamune, Yutaka Peeks, Martin D. Odell, Barbara Gong, Juliane Q. Herz, Laura M. Anderson, Harry L. |
| description | The smallest and most strained member of a family of π‐conjugated cyclic porphyrin oligomers was synthesized by using pentapyridyl templates based on ferrocene and corannulene. Both templates are effective for directing the synthesis of the butadiyne‐linked cyclic pentamer, despite the fact that the radii of their N5 donor sets are too small by 0.5 Å and 0.9 Å, respectively (from DFT calculations). The five‐porphyrin nanoring exhibits a structured absorption spectrum and its fluorescence extends to 1200 nm, reflecting strong π conjugation and Herzberg–Teller vibronic coupling.
Gerade groß genug: Zwei Template wurden für die Bildung eines π‐konjugierten cyclischen Porphyrinpentamers getestet. 1,3,5,7,9‐Penta(4‐pyridyl)corannulen war effektiver als ein Ferrocen‐basiertes Templat, obwohl der Radius seines N5‐Ligandensatzes fast 1 Å zu klein für den Hohlraum des Nanorings ist. |
| doi_str_mv | 10.1002/ange.201602909 |
| format | article |
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Gerade groß genug: Zwei Template wurden für die Bildung eines π‐konjugierten cyclischen Porphyrinpentamers getestet. 1,3,5,7,9‐Penta(4‐pyridyl)corannulen war effektiver als ein Ferrocen‐basiertes Templat, obwohl der Radius seines N5‐Ligandensatzes fast 1 Å zu klein für den Hohlraum des Nanorings ist.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201602909</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Absorption ; Absorption spectra ; Chemistry ; Corannulen-Derivate ; Coupling ; Ferrocen-Derivate ; Ferrocenes ; Fluorescence ; Gespannte Ringe ; Makrocyclen ; Mathematical analysis ; Nanostructure ; Oligomers ; Porphyrins ; Synthesis ; Templatsynthesen</subject><ispartof>Angewandte Chemie, 2016-07, Vol.128 (29), p.8498-8502</ispartof><rights>2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3679-8128f41b600bdfb8f2c131700faf332e52b9cbe919dc650b40eb67d177b5dd013</citedby><cites>FETCH-LOGICAL-c3679-8128f41b600bdfb8f2c131700faf332e52b9cbe919dc650b40eb67d177b5dd013</cites><orcidid>0000-0002-1801-8132</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Liu, Pengpeng</creatorcontrib><creatorcontrib>Hisamune, Yutaka</creatorcontrib><creatorcontrib>Peeks, Martin D.</creatorcontrib><creatorcontrib>Odell, Barbara</creatorcontrib><creatorcontrib>Gong, Juliane Q.</creatorcontrib><creatorcontrib>Herz, Laura M.</creatorcontrib><creatorcontrib>Anderson, Harry L.</creatorcontrib><title>Synthesis of Five-Porphyrin Nanorings by Using Ferrocene and Corannulene Templates</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>The smallest and most strained member of a family of π‐conjugated cyclic porphyrin oligomers was synthesized by using pentapyridyl templates based on ferrocene and corannulene. Both templates are effective for directing the synthesis of the butadiyne‐linked cyclic pentamer, despite the fact that the radii of their N5 donor sets are too small by 0.5 Å and 0.9 Å, respectively (from DFT calculations). The five‐porphyrin nanoring exhibits a structured absorption spectrum and its fluorescence extends to 1200 nm, reflecting strong π conjugation and Herzberg–Teller vibronic coupling.
Gerade groß genug: Zwei Template wurden für die Bildung eines π‐konjugierten cyclischen Porphyrinpentamers getestet. 1,3,5,7,9‐Penta(4‐pyridyl)corannulen war effektiver als ein Ferrocen‐basiertes Templat, obwohl der Radius seines N5‐Ligandensatzes fast 1 Å zu klein für den Hohlraum des Nanorings ist.</description><subject>Absorption</subject><subject>Absorption spectra</subject><subject>Chemistry</subject><subject>Corannulen-Derivate</subject><subject>Coupling</subject><subject>Ferrocen-Derivate</subject><subject>Ferrocenes</subject><subject>Fluorescence</subject><subject>Gespannte Ringe</subject><subject>Makrocyclen</subject><subject>Mathematical analysis</subject><subject>Nanostructure</subject><subject>Oligomers</subject><subject>Porphyrins</subject><subject>Synthesis</subject><subject>Templatsynthesen</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkU1vEzEQhi0EEqFw5bwSl142Hdvrr2OVNqFSCP0UR8venW23bOxgJ9D9990oqEIc4DQz0vO8Gukl5COFKQVgJy7c45QBlcAMmFdkQgWjJVdCvSYTgKoqNavMW_Iu50cAkEyZCbm-GcL2AXOXi9gW8-4nlpcxbR6G1IVi5UIc530u_FDc5XEr5phSrDFg4UJTzGJyIez6_X2L603vtpjfkzet6zN--D2PyN38_Hb2uVx-XVzMTpdlzaUypaZMtxX1EsA3rdctqymnCqB1LecMBfOm9mioaWopwFeAXqqGKuVF0wDlR-T4kLtJ8ccO89auu1xj37uAcZct1UwIyRkVI_rpL_Qx7lIYv7PUgBIgtdb_pDQwbqiu9lnTA1WnmHPC1m5St3ZpsBTsvgi7L8K-FDEK5iD86noc_kPb09Xi_E-3PLhd3uLTi-vSdyvVWK39tlrYL8vrqzMQl3bGnwE5AJpV</recordid><startdate>20160711</startdate><enddate>20160711</enddate><creator>Liu, Pengpeng</creator><creator>Hisamune, Yutaka</creator><creator>Peeks, Martin D.</creator><creator>Odell, Barbara</creator><creator>Gong, Juliane Q.</creator><creator>Herz, Laura M.</creator><creator>Anderson, Harry L.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>WIN</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><orcidid>https://orcid.org/0000-0002-1801-8132</orcidid></search><sort><creationdate>20160711</creationdate><title>Synthesis of Five-Porphyrin Nanorings by Using Ferrocene and Corannulene Templates</title><author>Liu, Pengpeng ; Hisamune, Yutaka ; Peeks, Martin D. ; Odell, Barbara ; Gong, Juliane Q. ; Herz, Laura M. ; Anderson, Harry L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3679-8128f41b600bdfb8f2c131700faf332e52b9cbe919dc650b40eb67d177b5dd013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Absorption</topic><topic>Absorption spectra</topic><topic>Chemistry</topic><topic>Corannulen-Derivate</topic><topic>Coupling</topic><topic>Ferrocen-Derivate</topic><topic>Ferrocenes</topic><topic>Fluorescence</topic><topic>Gespannte Ringe</topic><topic>Makrocyclen</topic><topic>Mathematical analysis</topic><topic>Nanostructure</topic><topic>Oligomers</topic><topic>Porphyrins</topic><topic>Synthesis</topic><topic>Templatsynthesen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Pengpeng</creatorcontrib><creatorcontrib>Hisamune, Yutaka</creatorcontrib><creatorcontrib>Peeks, Martin D.</creatorcontrib><creatorcontrib>Odell, Barbara</creatorcontrib><creatorcontrib>Gong, Juliane Q.</creatorcontrib><creatorcontrib>Herz, Laura M.</creatorcontrib><creatorcontrib>Anderson, Harry L.</creatorcontrib><collection>Istex</collection><collection>Wiley Open Access</collection><collection>Wiley Online Library Journals</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><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Pengpeng</au><au>Hisamune, Yutaka</au><au>Peeks, Martin D.</au><au>Odell, Barbara</au><au>Gong, Juliane Q.</au><au>Herz, Laura M.</au><au>Anderson, Harry L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Five-Porphyrin Nanorings by Using Ferrocene and Corannulene Templates</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2016-07-11</date><risdate>2016</risdate><volume>128</volume><issue>29</issue><spage>8498</spage><epage>8502</epage><pages>8498-8502</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The smallest and most strained member of a family of π‐conjugated cyclic porphyrin oligomers was synthesized by using pentapyridyl templates based on ferrocene and corannulene. Both templates are effective for directing the synthesis of the butadiyne‐linked cyclic pentamer, despite the fact that the radii of their N5 donor sets are too small by 0.5 Å and 0.9 Å, respectively (from DFT calculations). The five‐porphyrin nanoring exhibits a structured absorption spectrum and its fluorescence extends to 1200 nm, reflecting strong π conjugation and Herzberg–Teller vibronic coupling.
Gerade groß genug: Zwei Template wurden für die Bildung eines π‐konjugierten cyclischen Porphyrinpentamers getestet. 1,3,5,7,9‐Penta(4‐pyridyl)corannulen war effektiver als ein Ferrocen‐basiertes Templat, obwohl der Radius seines N5‐Ligandensatzes fast 1 Å zu klein für den Hohlraum des Nanorings ist.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ange.201602909</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1801-8132</orcidid><oa>free_for_read</oa></addata></record> |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Absorption Absorption spectra Chemistry Corannulen-Derivate Coupling Ferrocen-Derivate Ferrocenes Fluorescence Gespannte Ringe Makrocyclen Mathematical analysis Nanostructure Oligomers Porphyrins Synthesis Templatsynthesen |
| title | Synthesis of Five-Porphyrin Nanorings by Using Ferrocene and Corannulene Templates |
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