Pentacene-Fused Diporphyrins
In this work, we report the synthesis, spectroscopic characterization, and theoretical analysis of a linearly conjugated pentacene‐fused porphyrin dimer and cross‐conjugated quinone‐fused dinaphtho[2,3]porphyrins. These multichromophoric systems display non‐typical UV‐visible absorptions of either p...
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| Veröffentlicht in: | Chemistry : a European journal 2014-10, Vol.20 (43), p.13865-13870 |
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| container_title | Chemistry : a European journal |
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| creator | Jiang, Lin Engle, James T. Zaenglein, Ross A. Matus, Alex Ziegler, Christopher J. Wang, Hong Stillman, Martin J. |
| description | In this work, we report the synthesis, spectroscopic characterization, and theoretical analysis of a linearly conjugated pentacene‐fused porphyrin dimer and cross‐conjugated quinone‐fused dinaphtho[2,3]porphyrins. These multichromophoric systems display non‐typical UV‐visible absorptions of either porphyrins or pentacenes/quinones. UV‐visible, emission and magnetic circular dichroism (MCD) spectroscopy suggest strong electronic interactions among the multichromophores in the system. DFT calculations revealed the delocalization of the HOMOs and LUMOs spanning the entire dimer and linker assembly. The pentacene‐fused porphyrin dimer is significantly more stable than both the corresponding pentacene and the heptacene derivatives. The availability of these huge π‐extended and electronically highly interactive multichromophoric systems promises unprecedented electronic and photophysical properties.
Conjugated multichromophores: Pentacene‐ and pentaquinone‐fused diporphyrins were prepared. UV‐visible, emission, and magnetic circular dichroism (MCD) spectroscopy, and DFT calculations suggest strong electronic interactions among the multichromophores in the systems. |
| doi_str_mv | 10.1002/chem.201404591 |
| format | Article |
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Conjugated multichromophores: Pentacene‐ and pentaquinone‐fused diporphyrins were prepared. UV‐visible, emission, and magnetic circular dichroism (MCD) spectroscopy, and DFT calculations suggest strong electronic interactions among the multichromophores in the systems.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201404591</identifier><identifier>PMID: 25185525</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Chemistry ; Circular dichroism ; Circularity ; density functional calculations ; Dichroism ; Dimers ; Electronics ; Emission spectroscopy ; Interactive systems ; magnetic circular dichroism spectroscopy ; Mathematical analysis ; organic electronics ; pentacenes ; porphyrin dimers ; Porphyrins ; Quinones ; Spectroscopy ; Theoretical analysis ; π-extended porphyrins</subject><ispartof>Chemistry : a European journal, 2014-10, Vol.20 (43), p.13865-13870</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright Wiley Subscription Services, Inc. Oct 2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6411-30f155c3f465a942eeaed5f09e9899163184821a404ff52c730306acdc4b48593</citedby><cites>FETCH-LOGICAL-c6411-30f155c3f465a942eeaed5f09e9899163184821a404ff52c730306acdc4b48593</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201404591$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201404591$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25185525$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jiang, Lin</creatorcontrib><creatorcontrib>Engle, James T.</creatorcontrib><creatorcontrib>Zaenglein, Ross A.</creatorcontrib><creatorcontrib>Matus, Alex</creatorcontrib><creatorcontrib>Ziegler, Christopher J.</creatorcontrib><creatorcontrib>Wang, Hong</creatorcontrib><creatorcontrib>Stillman, Martin J.</creatorcontrib><title>Pentacene-Fused Diporphyrins</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>In this work, we report the synthesis, spectroscopic characterization, and theoretical analysis of a linearly conjugated pentacene‐fused porphyrin dimer and cross‐conjugated quinone‐fused dinaphtho[2,3]porphyrins. These multichromophoric systems display non‐typical UV‐visible absorptions of either porphyrins or pentacenes/quinones. UV‐visible, emission and magnetic circular dichroism (MCD) spectroscopy suggest strong electronic interactions among the multichromophores in the system. DFT calculations revealed the delocalization of the HOMOs and LUMOs spanning the entire dimer and linker assembly. The pentacene‐fused porphyrin dimer is significantly more stable than both the corresponding pentacene and the heptacene derivatives. The availability of these huge π‐extended and electronically highly interactive multichromophoric systems promises unprecedented electronic and photophysical properties.
Conjugated multichromophores: Pentacene‐ and pentaquinone‐fused diporphyrins were prepared. UV‐visible, emission, and magnetic circular dichroism (MCD) spectroscopy, and DFT calculations suggest strong electronic interactions among the multichromophores in the systems.</description><subject>Chemistry</subject><subject>Circular dichroism</subject><subject>Circularity</subject><subject>density functional calculations</subject><subject>Dichroism</subject><subject>Dimers</subject><subject>Electronics</subject><subject>Emission spectroscopy</subject><subject>Interactive systems</subject><subject>magnetic circular dichroism spectroscopy</subject><subject>Mathematical analysis</subject><subject>organic electronics</subject><subject>pentacenes</subject><subject>porphyrin dimers</subject><subject>Porphyrins</subject><subject>Quinones</subject><subject>Spectroscopy</subject><subject>Theoretical analysis</subject><subject>π-extended porphyrins</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkc1PGzEQxa2qVQmUKydUVeqFy6YztscfxyqFgARtpbbiaBlnVixNdoOdFeS_70ahEeqhnObye29m3hPiCGGMAPJTuuXFWAJq0OTxlRghSayUNfRajMBrWxlSfk_sl3IHAN4o9VbsSUJHJGkkjr9zu4qJW67O-sKzD1-aZZeXt-vctOWdeFPHeeHDp3kgfp2d_pycV5ffpheTz5dVMhqHbVAjUVK1NhS9lsyRZ1SDZ--8R6PQaScxDjfWNclkFSgwMc2SvtGOvDoQJ1vfZe7uey6rsGhK4vk8ttz1JaB1Bgkt6ZdRg2CNlA4G9OM_6F3X53Z4JMhhrQZJ0v-PQjMESN6pDTXeUil3pWSuwzI3i5jXASFsigibIsKuiEHw_sm2v1nwbIf_TX4A_BZ4aOa8fsEuTM5Pr56bV1ttU1b8uNPG_DsYqyyF66_T4MxEXVn5I0zVHyZPnmA</recordid><startdate>20141020</startdate><enddate>20141020</enddate><creator>Jiang, Lin</creator><creator>Engle, James T.</creator><creator>Zaenglein, Ross A.</creator><creator>Matus, Alex</creator><creator>Ziegler, Christopher J.</creator><creator>Wang, Hong</creator><creator>Stillman, Martin J.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20141020</creationdate><title>Pentacene-Fused Diporphyrins</title><author>Jiang, Lin ; Engle, James T. ; Zaenglein, Ross A. ; Matus, Alex ; Ziegler, Christopher J. ; Wang, Hong ; Stillman, Martin J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6411-30f155c3f465a942eeaed5f09e9899163184821a404ff52c730306acdc4b48593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Chemistry</topic><topic>Circular dichroism</topic><topic>Circularity</topic><topic>density functional calculations</topic><topic>Dichroism</topic><topic>Dimers</topic><topic>Electronics</topic><topic>Emission spectroscopy</topic><topic>Interactive systems</topic><topic>magnetic circular dichroism spectroscopy</topic><topic>Mathematical analysis</topic><topic>organic electronics</topic><topic>pentacenes</topic><topic>porphyrin dimers</topic><topic>Porphyrins</topic><topic>Quinones</topic><topic>Spectroscopy</topic><topic>Theoretical analysis</topic><topic>π-extended porphyrins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Lin</creatorcontrib><creatorcontrib>Engle, James T.</creatorcontrib><creatorcontrib>Zaenglein, Ross A.</creatorcontrib><creatorcontrib>Matus, Alex</creatorcontrib><creatorcontrib>Ziegler, Christopher J.</creatorcontrib><creatorcontrib>Wang, Hong</creatorcontrib><creatorcontrib>Stillman, Martin J.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Lin</au><au>Engle, James T.</au><au>Zaenglein, Ross A.</au><au>Matus, Alex</au><au>Ziegler, Christopher J.</au><au>Wang, Hong</au><au>Stillman, Martin J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pentacene-Fused Diporphyrins</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-10-20</date><risdate>2014</risdate><volume>20</volume><issue>43</issue><spage>13865</spage><epage>13870</epage><pages>13865-13870</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>In this work, we report the synthesis, spectroscopic characterization, and theoretical analysis of a linearly conjugated pentacene‐fused porphyrin dimer and cross‐conjugated quinone‐fused dinaphtho[2,3]porphyrins. These multichromophoric systems display non‐typical UV‐visible absorptions of either porphyrins or pentacenes/quinones. UV‐visible, emission and magnetic circular dichroism (MCD) spectroscopy suggest strong electronic interactions among the multichromophores in the system. DFT calculations revealed the delocalization of the HOMOs and LUMOs spanning the entire dimer and linker assembly. The pentacene‐fused porphyrin dimer is significantly more stable than both the corresponding pentacene and the heptacene derivatives. The availability of these huge π‐extended and electronically highly interactive multichromophoric systems promises unprecedented electronic and photophysical properties.
Conjugated multichromophores: Pentacene‐ and pentaquinone‐fused diporphyrins were prepared. UV‐visible, emission, and magnetic circular dichroism (MCD) spectroscopy, and DFT calculations suggest strong electronic interactions among the multichromophores in the systems.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25185525</pmid><doi>10.1002/chem.201404591</doi><tpages>6</tpages></addata></record> |
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| subjects | Chemistry Circular dichroism Circularity density functional calculations Dichroism Dimers Electronics Emission spectroscopy Interactive systems magnetic circular dichroism spectroscopy Mathematical analysis organic electronics pentacenes porphyrin dimers Porphyrins Quinones Spectroscopy Theoretical analysis π-extended porphyrins |
| title | Pentacene-Fused Diporphyrins |
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