Synthesis and Spectroscopy of a Series of Substituted N-Confused Tetraphenylporphyrins
A series of N-confused tetraphenylporphyrins (H2NCTPPs) with substituents on either the para- or the 3,5-positions of the meso phenyl rings were prepared using Lindsey conditions. Both electron-withdrawing and electron-donating groups were chosen in order to probe the effects of peripheral substitut...
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| Veröffentlicht in: | Journal of organic chemistry 2004-10, Vol.69 (22), p.7423-7427 |
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| container_issue | 22 |
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| container_title | Journal of organic chemistry |
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| creator | Shaw, Janet L Garrison, Shana A Alemán, Elvin A Ziegler, Christopher J Modarelli, David A |
| description | A series of N-confused tetraphenylporphyrins (H2NCTPPs) with substituents on either the para- or the 3,5-positions of the meso phenyl rings were prepared using Lindsey conditions. Both electron-withdrawing and electron-donating groups were chosen in order to probe the effects of peripheral substitution on the properties of the macrocycles. The series includes 5,10,15,20-tetra-(4-R-phenyl) N-confused porphyrins (where R = bromo (1), iodo (2), cyano (3), methoxy (4), 2‘,5‘-dimethoxyphenyl (5), or ethynyl (6)) and 5,10,15,20-(3,5-di-tert-butylphenyl) N-confused porphyrin (7). Absorption and steady-state fluorescence measurements were carried out, and quantum yields were measured for all compounds in both dichloromethane (CH2Cl2) and dimethylacetamide (DMAc). |
| doi_str_mv | 10.1021/jo049199e |
| format | Article |
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Both electron-withdrawing and electron-donating groups were chosen in order to probe the effects of peripheral substitution on the properties of the macrocycles. The series includes 5,10,15,20-tetra-(4-R-phenyl) N-confused porphyrins (where R = bromo (1), iodo (2), cyano (3), methoxy (4), 2‘,5‘-dimethoxyphenyl (5), or ethynyl (6)) and 5,10,15,20-(3,5-di-tert-butylphenyl) N-confused porphyrin (7). 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Org. Chem</addtitle><description>A series of N-confused tetraphenylporphyrins (H2NCTPPs) with substituents on either the para- or the 3,5-positions of the meso phenyl rings were prepared using Lindsey conditions. Both electron-withdrawing and electron-donating groups were chosen in order to probe the effects of peripheral substitution on the properties of the macrocycles. The series includes 5,10,15,20-tetra-(4-R-phenyl) N-confused porphyrins (where R = bromo (1), iodo (2), cyano (3), methoxy (4), 2‘,5‘-dimethoxyphenyl (5), or ethynyl (6)) and 5,10,15,20-(3,5-di-tert-butylphenyl) N-confused porphyrin (7). Absorption and steady-state fluorescence measurements were carried out, and quantum yields were measured for all compounds in both dichloromethane (CH2Cl2) and dimethylacetamide (DMAc).</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptkEFv1DAQhS0EokvhwB9AuYDEIWDHsZM5wgIFVBWkLFwt25loU7JJ6nEk8u9xtavuhbnMk-bT05vH2EvB3wleiPe3Ey9BAOAjthGq4LkGXj5mG86LIpeFlhfsGdEtT6OUesouhCqhAq027HezjnGP1FNmxzZrZvQxTOSnec2mLrNZg6FHutfN4ij2cYnYZjf5dhq7hZLcYQx23uO4DvMU5v0a-pGesyedHQhfnPYl-_Xl8277Nb_-cfVt--E6t2WpYsrZQut0DehUK0Vphaxr5FxAJdvad76WXjhZVI4rlF0F3nuwjoMvJFfOyUv25ug7h-luQYrm0JPHYbAjTgsZrQFqAJ7At0fQp-8oYGfm0B9sWI3g5r5E81BiYl-dTBd3wPZMnlpLwOsTYMnboQt29D2dOV2I5FQmLj9yPUX8-3C34Y_RlayU2f1szNWNqj7p72A-nn2tp5RnCWPq7j8B_wEtcpWE</recordid><startdate>20041029</startdate><enddate>20041029</enddate><creator>Shaw, Janet L</creator><creator>Garrison, Shana A</creator><creator>Alemán, Elvin A</creator><creator>Ziegler, Christopher J</creator><creator>Modarelli, David A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20041029</creationdate><title>Synthesis and Spectroscopy of a Series of Substituted N-Confused Tetraphenylporphyrins</title><author>Shaw, Janet L ; Garrison, Shana A ; Alemán, Elvin A ; Ziegler, Christopher J ; Modarelli, David A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-69d9db689eb5d314a1388e001973d8cfc83c1b327b05e3f79ccc9ab09c2305bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shaw, Janet L</creatorcontrib><creatorcontrib>Garrison, Shana A</creatorcontrib><creatorcontrib>Alemán, Elvin A</creatorcontrib><creatorcontrib>Ziegler, Christopher J</creatorcontrib><creatorcontrib>Modarelli, David A</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shaw, Janet L</au><au>Garrison, Shana A</au><au>Alemán, Elvin A</au><au>Ziegler, Christopher J</au><au>Modarelli, David A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Spectroscopy of a Series of Substituted N-Confused Tetraphenylporphyrins</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-10-29</date><risdate>2004</risdate><volume>69</volume><issue>22</issue><spage>7423</spage><epage>7427</epage><pages>7423-7427</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A series of N-confused tetraphenylporphyrins (H2NCTPPs) with substituents on either the para- or the 3,5-positions of the meso phenyl rings were prepared using Lindsey conditions. Both electron-withdrawing and electron-donating groups were chosen in order to probe the effects of peripheral substitution on the properties of the macrocycles. The series includes 5,10,15,20-tetra-(4-R-phenyl) N-confused porphyrins (where R = bromo (1), iodo (2), cyano (3), methoxy (4), 2‘,5‘-dimethoxyphenyl (5), or ethynyl (6)) and 5,10,15,20-(3,5-di-tert-butylphenyl) N-confused porphyrin (7). Absorption and steady-state fluorescence measurements were carried out, and quantum yields were measured for all compounds in both dichloromethane (CH2Cl2) and dimethylacetamide (DMAc).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15497965</pmid><doi>10.1021/jo049199e</doi><tpages>5</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties |
| title | Synthesis and Spectroscopy of a Series of Substituted N-Confused Tetraphenylporphyrins |
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