Synthesis and Electrochemical and Photophysical Studies of Tetrathiafulvalene-Annulated Phthalocyanines
The synthesis of tetrakis(tetrathiafulvalene)-annulated metal-free and metallophthalocyanines 5−8 via the tetramerization of the phthalonitrile derivative 4 is reported. All of them have been fully characterized by electronic absorption spectroscopy, thin-layer cyclic voltammetry, mass spectrometry,...
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| Veröffentlicht in: | Journal of organic chemistry 2005-06, Vol.70 (13), p.4988-4992 |
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| container_end_page | 4992 |
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| container_issue | 13 |
| container_start_page | 4988 |
| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Loosli, Claudia Jia, Chunyang Liu, Shi-Xia Haas, Marco Dias, Marylène Levillain, Eric Neels, Antonia Labat, Gael Hauser, Andreas Decurtins, Silvio |
| description | The synthesis of tetrakis(tetrathiafulvalene)-annulated metal-free and metallophthalocyanines 5−8 via the tetramerization of the phthalonitrile derivative 4 is reported. All of them have been fully characterized by electronic absorption spectroscopy, thin-layer cyclic voltammetry, mass spectrometry, and elemental analysis. Their solution electrochemical data show two reversible four-electron oxidation waves, indicating that these fused systems are strong π-electron donors, which give rise to tetra- or octaradical cation species. For the metal-free phthalocyanine 5, additionally a reversible one-electron wave was found in the negative direction arising from the reduction of the macrocycle. Moreover, the tetrathiafulvalene unit acts as an efficient reductive electron-transfer quencher for the phthalocyanine emission, but upon its oxidation, an intense luminescence is switched on. |
| doi_str_mv | 10.1021/jo0501801 |
| format | Article |
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All of them have been fully characterized by electronic absorption spectroscopy, thin-layer cyclic voltammetry, mass spectrometry, and elemental analysis. Their solution electrochemical data show two reversible four-electron oxidation waves, indicating that these fused systems are strong π-electron donors, which give rise to tetra- or octaradical cation species. For the metal-free phthalocyanine 5, additionally a reversible one-electron wave was found in the negative direction arising from the reduction of the macrocycle. 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Org. Chem</addtitle><description>The synthesis of tetrakis(tetrathiafulvalene)-annulated metal-free and metallophthalocyanines 5−8 via the tetramerization of the phthalonitrile derivative 4 is reported. All of them have been fully characterized by electronic absorption spectroscopy, thin-layer cyclic voltammetry, mass spectrometry, and elemental analysis. Their solution electrochemical data show two reversible four-electron oxidation waves, indicating that these fused systems are strong π-electron donors, which give rise to tetra- or octaradical cation species. For the metal-free phthalocyanine 5, additionally a reversible one-electron wave was found in the negative direction arising from the reduction of the macrocycle. Moreover, the tetrathiafulvalene unit acts as an efficient reductive electron-transfer quencher for the phthalocyanine emission, but upon its oxidation, an intense luminescence is switched on.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</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>2005</creationdate><recordtype>article</recordtype><recordid>eNptkM1uEzEUhS1ERUNhwQugbEBiMdT2jO2ZZQnlpyqiUoLEzrrx3GFcHDvYHkTeHreJmk29sXX83aNzDyGvGH3PKGfnt4EKylrKnpAZE5xWsqPNUzKjlPOq5rI-Jc9TuqXlCCGekVMmOkmbTs7Ir-XO5xGTTXPw_fzSockxmBE31oC7127GkMN23KV7ZZmn3mKah2G-whwhjxaGyf0Fhx6rC-8nBxnvpvIILpgdeOsxvSAnA7iELw_3Gfnx6XK1-FJdf__8dXFxXUHT8lwx4H3NkaleNEIZOtRranrGG9MgdEoZI-UgayyvoYNetq3oTRGxrG3WQtVn5O3edxvDnwlT1hubDDoHHsOUtFRd0wolCvhuD5oYUoo46G20G4g7zai-a1U_tFrY1wfTab3B_kgeaizAmwMAqZQ0RPDGpiMn266Tsitctedsyvjv4R_i7xKsVkKvbpZa1Vfi47cPC_3z6AsmlTxT9KW7RwL-B5c7nAw</recordid><startdate>20050624</startdate><enddate>20050624</enddate><creator>Loosli, Claudia</creator><creator>Jia, Chunyang</creator><creator>Liu, Shi-Xia</creator><creator>Haas, Marco</creator><creator>Dias, Marylène</creator><creator>Levillain, Eric</creator><creator>Neels, Antonia</creator><creator>Labat, Gael</creator><creator>Hauser, Andreas</creator><creator>Decurtins, Silvio</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>20050624</creationdate><title>Synthesis and Electrochemical and Photophysical Studies of Tetrathiafulvalene-Annulated Phthalocyanines</title><author>Loosli, Claudia ; Jia, Chunyang ; Liu, Shi-Xia ; Haas, Marco ; Dias, Marylène ; Levillain, Eric ; Neels, Antonia ; Labat, Gael ; Hauser, Andreas ; Decurtins, Silvio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a482t-1a2d32e17d5457c0f3b0cd124c4ea977cc66f63e77cf9ad6885dccc6e152cb573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Loosli, Claudia</creatorcontrib><creatorcontrib>Jia, Chunyang</creatorcontrib><creatorcontrib>Liu, Shi-Xia</creatorcontrib><creatorcontrib>Haas, Marco</creatorcontrib><creatorcontrib>Dias, Marylène</creatorcontrib><creatorcontrib>Levillain, Eric</creatorcontrib><creatorcontrib>Neels, Antonia</creatorcontrib><creatorcontrib>Labat, Gael</creatorcontrib><creatorcontrib>Hauser, Andreas</creatorcontrib><creatorcontrib>Decurtins, Silvio</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>Loosli, Claudia</au><au>Jia, Chunyang</au><au>Liu, Shi-Xia</au><au>Haas, Marco</au><au>Dias, Marylène</au><au>Levillain, Eric</au><au>Neels, Antonia</au><au>Labat, Gael</au><au>Hauser, Andreas</au><au>Decurtins, Silvio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Electrochemical and Photophysical Studies of Tetrathiafulvalene-Annulated Phthalocyanines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-06-24</date><risdate>2005</risdate><volume>70</volume><issue>13</issue><spage>4988</spage><epage>4992</epage><pages>4988-4992</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The synthesis of tetrakis(tetrathiafulvalene)-annulated metal-free and metallophthalocyanines 5−8 via the tetramerization of the phthalonitrile derivative 4 is reported. All of them have been fully characterized by electronic absorption spectroscopy, thin-layer cyclic voltammetry, mass spectrometry, and elemental analysis. Their solution electrochemical data show two reversible four-electron oxidation waves, indicating that these fused systems are strong π-electron donors, which give rise to tetra- or octaradical cation species. For the metal-free phthalocyanine 5, additionally a reversible one-electron wave was found in the negative direction arising from the reduction of the macrocycle. 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| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties |
| title | Synthesis and Electrochemical and Photophysical Studies of Tetrathiafulvalene-Annulated Phthalocyanines |
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