Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound
Treatment of a meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding porphyrinquinone in a high yield (91%). A novel quinone derived from meso‐meso β–β doubly‐fused diporphyrin was obtained as the sole byproduct (16% yield), which exhibits str...
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Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2020-10, Vol.15 (19), p.3037-3043 |
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creator | Yamashita, Ken‐ichi Hirano, Daisuke Fujimaki, Keisuke Sugiura, Ken‐ichi |
description | Treatment of a meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding porphyrinquinone in a high yield (91%). A novel quinone derived from meso‐meso β–β doubly‐fused diporphyrin was obtained as the sole byproduct (16% yield), which exhibits strong panchromatic absorption between 300 and 1000 nm. It has a low HOMO‐LUMO gap owing to expanded and low‐symmetry π‐planes.
Treatment of meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding quinone in high yield. A novel quinone derived from meso‐meso β–β doubly‐linked diporphyrin is obtained as the sole byproduct. It exhibits strong panchromatic absorption between 300–1000 nm and has a narrow HOMO‐LUMO gap. |
doi_str_mv | 10.1002/asia.202000781 |
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Treatment of meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding quinone in high yield. A novel quinone derived from meso‐meso β–β doubly‐linked diporphyrin is obtained as the sole byproduct. It exhibits strong panchromatic absorption between 300–1000 nm and has a narrow HOMO‐LUMO gap.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.202000781</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Chemistry ; Iodine compounds ; Molecular orbitals ; Oxidation ; Panchromatic absorption ; Porphyrinoids ; Propionic acid ; Quinones ; Tautomerism</subject><ispartof>Chemistry, an Asian journal, 2020-10, Vol.15 (19), p.3037-3043</ispartof><rights>2020 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3871-39b68342df306506ca503eb9ef339fc9fc33b3a070e6b6abe6b82674b977b6473</citedby><cites>FETCH-LOGICAL-c3871-39b68342df306506ca503eb9ef339fc9fc33b3a070e6b6abe6b82674b977b6473</cites><orcidid>0000-0001-7270-1234 ; 0000-0003-1011-2412</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.202000781$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.202000781$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Yamashita, Ken‐ichi</creatorcontrib><creatorcontrib>Hirano, Daisuke</creatorcontrib><creatorcontrib>Fujimaki, Keisuke</creatorcontrib><creatorcontrib>Sugiura, Ken‐ichi</creatorcontrib><title>Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound</title><title>Chemistry, an Asian journal</title><description>Treatment of a meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding porphyrinquinone in a high yield (91%). A novel quinone derived from meso‐meso β–β doubly‐fused diporphyrin was obtained as the sole byproduct (16% yield), which exhibits strong panchromatic absorption between 300 and 1000 nm. It has a low HOMO‐LUMO gap owing to expanded and low‐symmetry π‐planes.
Treatment of meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding quinone in high yield. A novel quinone derived from meso‐meso β–β doubly‐linked diporphyrin is obtained as the sole byproduct. It exhibits strong panchromatic absorption between 300–1000 nm and has a narrow HOMO‐LUMO gap.</description><subject>Chemistry</subject><subject>Iodine compounds</subject><subject>Molecular orbitals</subject><subject>Oxidation</subject><subject>Panchromatic absorption</subject><subject>Porphyrinoids</subject><subject>Propionic acid</subject><subject>Quinones</subject><subject>Tautomerism</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkUFLwzAUx4soOKdXzwEvXjZfmi5pj2NzbjCYsg28lbRNt4wu6ZJV7c1PIH5GP4kZmxO8yAvvJfD7_3nk73nXGNoYwL_jVvK2Dz4AsBCfeA0cUtwKGH4-Pd798Ny7sHYF0PEhChvex7RW26Ww0iKdo0dtymVtpNpUUmklEFcZ6usqKeqv989BZYV7yvKHQk8HbLY0ulos0eRNZnwrtdqZ9SU3dXGELZpbqRaIo2FdCvPCC6G2aKQz6Qx6el3qSmWX3lnOCyuuDrPpzQf3s96wNZ48jHrdcSslIcMtEiU0JIGf5QRoB2jKO0BEEomckChP3SEkIRwYCJpQnrge-pQFScRYQgNGmt7t3rc0elMJu43X0qaiKLgSurKxHxAgjGFGHHrzB13pyii3naMC5grozrC9p1KjrTUij0sj1-4DYgzxLp54F098jMcJor3gVRai_oeOu9NR91f7DUDZl9Q</recordid><startdate>20201001</startdate><enddate>20201001</enddate><creator>Yamashita, Ken‐ichi</creator><creator>Hirano, Daisuke</creator><creator>Fujimaki, Keisuke</creator><creator>Sugiura, Ken‐ichi</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7270-1234</orcidid><orcidid>https://orcid.org/0000-0003-1011-2412</orcidid></search><sort><creationdate>20201001</creationdate><title>Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound</title><author>Yamashita, Ken‐ichi ; Hirano, Daisuke ; Fujimaki, Keisuke ; Sugiura, Ken‐ichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3871-39b68342df306506ca503eb9ef339fc9fc33b3a070e6b6abe6b82674b977b6473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Iodine compounds</topic><topic>Molecular orbitals</topic><topic>Oxidation</topic><topic>Panchromatic absorption</topic><topic>Porphyrinoids</topic><topic>Propionic acid</topic><topic>Quinones</topic><topic>Tautomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamashita, Ken‐ichi</creatorcontrib><creatorcontrib>Hirano, Daisuke</creatorcontrib><creatorcontrib>Fujimaki, Keisuke</creatorcontrib><creatorcontrib>Sugiura, Ken‐ichi</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamashita, Ken‐ichi</au><au>Hirano, Daisuke</au><au>Fujimaki, Keisuke</au><au>Sugiura, Ken‐ichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound</atitle><jtitle>Chemistry, an Asian journal</jtitle><date>2020-10-01</date><risdate>2020</risdate><volume>15</volume><issue>19</issue><spage>3037</spage><epage>3043</epage><pages>3037-3043</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Treatment of a meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding porphyrinquinone in a high yield (91%). A novel quinone derived from meso‐meso β–β doubly‐fused diporphyrin was obtained as the sole byproduct (16% yield), which exhibits strong panchromatic absorption between 300 and 1000 nm. It has a low HOMO‐LUMO gap owing to expanded and low‐symmetry π‐planes.
Treatment of meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding quinone in high yield. A novel quinone derived from meso‐meso β–β doubly‐linked diporphyrin is obtained as the sole byproduct. It exhibits strong panchromatic absorption between 300–1000 nm and has a narrow HOMO‐LUMO gap.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/asia.202000781</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7270-1234</orcidid><orcidid>https://orcid.org/0000-0003-1011-2412</orcidid></addata></record> |
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source | Wiley Online Library Journals Frontfile Complete |
subjects | Chemistry Iodine compounds Molecular orbitals Oxidation Panchromatic absorption Porphyrinoids Propionic acid Quinones Tautomerism |
title | Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound |
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