Synthesis and Spectroscopic and Electrochemical Studies of Pyrazine- or Pyridine-Ring-Fused Tetraazachlorins, Bacteriochlorins, and Isobacteriochlorins
Mixed condensation of tetramethylsuccinonitrile and either 2,3-dicyano-5,6-diethylpyrazine, 2,3-dicyanopyridine, or 3,4-pyridinedicarboximide in the presence of nickel chloride forms novel pyrazine-, 2,3-pyridine-, or 3,4-pyridine-ring-fused tetraazachlorin (TAC), tetraazabacteriochlorin (TABC), and...
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| Veröffentlicht in: | Inorganic chemistry 2009-01, Vol.48 (1), p.164-173 |
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| container_title | Inorganic chemistry |
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| creator | Makarova, Elena A Dzyuina, Ekaterina V Fukuda, Takamitsu Kaneko, Hironori Hashimoto, Naoaki Kikukawa, Yuu Kobayashi, Nagao Lukyanets, Evgeny A |
| description | Mixed condensation of tetramethylsuccinonitrile and either 2,3-dicyano-5,6-diethylpyrazine, 2,3-dicyanopyridine, or 3,4-pyridinedicarboximide in the presence of nickel chloride forms novel pyrazine-, 2,3-pyridine-, or 3,4-pyridine-ring-fused tetraazachlorin (TAC), tetraazabacteriochlorin (TABC), and tetraazaisobacteriochlorin (TAiBC) derivatives. All possible structural isomers were separated using repeated thin-layer chromatography and have been investigated by absorption and magnetic circular dichroism spectroscopy. Similarly to previously reported TAC analogues, the TAC and TABC derivatives show large splitting of the Q band, while a single, intense absorption band is observed for the TAiBC derivatives. Although the absorption spectra are practically identical in shape for the separated structural isomers of TACs and TABCs, the Q-band maxima of the TAiBCs depend significantly on their structures. The observed spectroscopic properties were interpreted on the basis of electrochemical data and the results of (time-dependent) DFT calculations. |
| doi_str_mv | 10.1021/ic801552u |
| format | Article |
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All possible structural isomers were separated using repeated thin-layer chromatography and have been investigated by absorption and magnetic circular dichroism spectroscopy. Similarly to previously reported TAC analogues, the TAC and TABC derivatives show large splitting of the Q band, while a single, intense absorption band is observed for the TAiBC derivatives. Although the absorption spectra are practically identical in shape for the separated structural isomers of TACs and TABCs, the Q-band maxima of the TAiBCs depend significantly on their structures. The observed spectroscopic properties were interpreted on the basis of electrochemical data and the results of (time-dependent) DFT calculations.</description><identifier>ISSN: 0020-1669</identifier><identifier>EISSN: 1520-510X</identifier><identifier>DOI: 10.1021/ic801552u</identifier><identifier>PMID: 19049420</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Absorption ; Aza Compounds - chemistry ; Circular Dichroism ; Electrochemistry ; Isomerism ; Magnetic Resonance Spectroscopy ; Magnetics ; Nitrogen - chemistry ; Photosensitizing Agents - chemistry ; Photosensitizing Agents - isolation & purification ; Porphyrins - chemistry ; Porphyrins - isolation & purification ; Pyrazines - chemistry ; Pyridines - chemistry ; Quantum Theory ; Spectrophotometry, Ultraviolet ; Time Factors</subject><ispartof>Inorganic chemistry, 2009-01, Vol.48 (1), p.164-173</ispartof><rights>Copyright © 2009 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-49ad63407339d8362f256e7fedf35ba5c7a737f8e249e3b24be136bbd284dfc83</citedby><cites>FETCH-LOGICAL-a379t-49ad63407339d8362f256e7fedf35ba5c7a737f8e249e3b24be136bbd284dfc83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ic801552u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ic801552u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19049420$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Makarova, Elena A</creatorcontrib><creatorcontrib>Dzyuina, Ekaterina V</creatorcontrib><creatorcontrib>Fukuda, Takamitsu</creatorcontrib><creatorcontrib>Kaneko, Hironori</creatorcontrib><creatorcontrib>Hashimoto, Naoaki</creatorcontrib><creatorcontrib>Kikukawa, Yuu</creatorcontrib><creatorcontrib>Kobayashi, Nagao</creatorcontrib><creatorcontrib>Lukyanets, Evgeny A</creatorcontrib><title>Synthesis and Spectroscopic and Electrochemical Studies of Pyrazine- or Pyridine-Ring-Fused Tetraazachlorins, Bacteriochlorins, and Isobacteriochlorins</title><title>Inorganic chemistry</title><addtitle>Inorg. Chem</addtitle><description>Mixed condensation of tetramethylsuccinonitrile and either 2,3-dicyano-5,6-diethylpyrazine, 2,3-dicyanopyridine, or 3,4-pyridinedicarboximide in the presence of nickel chloride forms novel pyrazine-, 2,3-pyridine-, or 3,4-pyridine-ring-fused tetraazachlorin (TAC), tetraazabacteriochlorin (TABC), and tetraazaisobacteriochlorin (TAiBC) derivatives. All possible structural isomers were separated using repeated thin-layer chromatography and have been investigated by absorption and magnetic circular dichroism spectroscopy. Similarly to previously reported TAC analogues, the TAC and TABC derivatives show large splitting of the Q band, while a single, intense absorption band is observed for the TAiBC derivatives. Although the absorption spectra are practically identical in shape for the separated structural isomers of TACs and TABCs, the Q-band maxima of the TAiBCs depend significantly on their structures. The observed spectroscopic properties were interpreted on the basis of electrochemical data and the results of (time-dependent) DFT calculations.</description><subject>Absorption</subject><subject>Aza Compounds - chemistry</subject><subject>Circular Dichroism</subject><subject>Electrochemistry</subject><subject>Isomerism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Magnetics</subject><subject>Nitrogen - chemistry</subject><subject>Photosensitizing Agents - chemistry</subject><subject>Photosensitizing Agents - isolation & purification</subject><subject>Porphyrins - chemistry</subject><subject>Porphyrins - isolation & purification</subject><subject>Pyrazines - chemistry</subject><subject>Pyridines - chemistry</subject><subject>Quantum Theory</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Time Factors</subject><issn>0020-1669</issn><issn>1520-510X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9Kw0AQxhdRbK0efAHJRUEwuv-yyR61WBUKilXwFja7E7uSZutucmhfxNc1tcWCeJqZb358w8wgdEzwJcGUXFmdYZIktN1BfZJQHCcEv-2iPsZdToSQPXQQwgfGWDIu9lGPSMwlp7iPviaLuplCsCFStYkmc9CNd0G7udU_ym31o-gpzKxWVTRpWmMhRK6MnhZeLW0NceT8qrBmVTzb-j0etQFM9AKNV2qp9LRy3tbhIrpRugFv3VZZzXgIrvjTOER7paoCHG3iAL2Obl-G9_H48e5heD2OFUtlE3OpjGAcp4xJkzFBS5oISEswJUsKlehUpSwtM6BcAisoL4AwURSGZtyUOmMDdLb2nXv32UJo8pkNGqpK1eDakAuRppInuAPP16DuzhM8lPnc25nyi5zgfPWF_PcLHXuyMW2LGZgtuTl7B5yuAaVD_uFaX3c7_mP0DduxkjM</recordid><startdate>20090105</startdate><enddate>20090105</enddate><creator>Makarova, Elena A</creator><creator>Dzyuina, Ekaterina V</creator><creator>Fukuda, Takamitsu</creator><creator>Kaneko, Hironori</creator><creator>Hashimoto, Naoaki</creator><creator>Kikukawa, Yuu</creator><creator>Kobayashi, Nagao</creator><creator>Lukyanets, Evgeny A</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090105</creationdate><title>Synthesis and Spectroscopic and Electrochemical Studies of Pyrazine- or Pyridine-Ring-Fused Tetraazachlorins, Bacteriochlorins, and Isobacteriochlorins</title><author>Makarova, Elena A ; Dzyuina, Ekaterina V ; Fukuda, Takamitsu ; Kaneko, Hironori ; Hashimoto, Naoaki ; Kikukawa, Yuu ; Kobayashi, Nagao ; Lukyanets, Evgeny A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-49ad63407339d8362f256e7fedf35ba5c7a737f8e249e3b24be136bbd284dfc83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Absorption</topic><topic>Aza Compounds - chemistry</topic><topic>Circular Dichroism</topic><topic>Electrochemistry</topic><topic>Isomerism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Magnetics</topic><topic>Nitrogen - chemistry</topic><topic>Photosensitizing Agents - chemistry</topic><topic>Photosensitizing Agents - isolation & purification</topic><topic>Porphyrins - chemistry</topic><topic>Porphyrins - isolation & purification</topic><topic>Pyrazines - chemistry</topic><topic>Pyridines - chemistry</topic><topic>Quantum Theory</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Time Factors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Makarova, Elena A</creatorcontrib><creatorcontrib>Dzyuina, Ekaterina V</creatorcontrib><creatorcontrib>Fukuda, Takamitsu</creatorcontrib><creatorcontrib>Kaneko, Hironori</creatorcontrib><creatorcontrib>Hashimoto, Naoaki</creatorcontrib><creatorcontrib>Kikukawa, Yuu</creatorcontrib><creatorcontrib>Kobayashi, Nagao</creatorcontrib><creatorcontrib>Lukyanets, Evgeny A</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Makarova, Elena A</au><au>Dzyuina, Ekaterina V</au><au>Fukuda, Takamitsu</au><au>Kaneko, Hironori</au><au>Hashimoto, Naoaki</au><au>Kikukawa, Yuu</au><au>Kobayashi, Nagao</au><au>Lukyanets, Evgeny A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Spectroscopic and Electrochemical Studies of Pyrazine- or Pyridine-Ring-Fused Tetraazachlorins, Bacteriochlorins, and Isobacteriochlorins</atitle><jtitle>Inorganic chemistry</jtitle><addtitle>Inorg. Chem</addtitle><date>2009-01-05</date><risdate>2009</risdate><volume>48</volume><issue>1</issue><spage>164</spage><epage>173</epage><pages>164-173</pages><issn>0020-1669</issn><eissn>1520-510X</eissn><abstract>Mixed condensation of tetramethylsuccinonitrile and either 2,3-dicyano-5,6-diethylpyrazine, 2,3-dicyanopyridine, or 3,4-pyridinedicarboximide in the presence of nickel chloride forms novel pyrazine-, 2,3-pyridine-, or 3,4-pyridine-ring-fused tetraazachlorin (TAC), tetraazabacteriochlorin (TABC), and tetraazaisobacteriochlorin (TAiBC) derivatives. All possible structural isomers were separated using repeated thin-layer chromatography and have been investigated by absorption and magnetic circular dichroism spectroscopy. Similarly to previously reported TAC analogues, the TAC and TABC derivatives show large splitting of the Q band, while a single, intense absorption band is observed for the TAiBC derivatives. Although the absorption spectra are practically identical in shape for the separated structural isomers of TACs and TABCs, the Q-band maxima of the TAiBCs depend significantly on their structures. The observed spectroscopic properties were interpreted on the basis of electrochemical data and the results of (time-dependent) DFT calculations.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19049420</pmid><doi>10.1021/ic801552u</doi><tpages>10</tpages></addata></record> |
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| subjects | Absorption Aza Compounds - chemistry Circular Dichroism Electrochemistry Isomerism Magnetic Resonance Spectroscopy Magnetics Nitrogen - chemistry Photosensitizing Agents - chemistry Photosensitizing Agents - isolation & purification Porphyrins - chemistry Porphyrins - isolation & purification Pyrazines - chemistry Pyridines - chemistry Quantum Theory Spectrophotometry, Ultraviolet Time Factors |
| title | Synthesis and Spectroscopic and Electrochemical Studies of Pyrazine- or Pyridine-Ring-Fused Tetraazachlorins, Bacteriochlorins, and Isobacteriochlorins |
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