3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation
We have designed and synthesized 3,6,13,16-tetrapropylporphycene for the first time as its alkyl analogue from ethyl 4-propyl-1H-pyrrole-2-carboxylate. The substituent effect was found to be more intense than reported positional isomeric tetrapropylporphycenes. The freebase porphycene exhibited mode...
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| Veröffentlicht in: | Journal of organic chemistry 2022-03, Vol.87 (5), p.2721-2729 |
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| container_end_page | 2729 |
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| container_issue | 5 |
| container_start_page | 2721 |
| container_title | Journal of organic chemistry |
| container_volume | 87 |
| creator | Nagamaiah, Jodukathula Dutta, Arnab Pati, Narendra Nath Sahoo, Sameeta Soman, Rahul Panda, Pradeepta K |
| description | We have designed and synthesized 3,6,13,16-tetrapropylporphycene for the first time as its alkyl analogue from ethyl 4-propyl-1H-pyrrole-2-carboxylate. The substituent effect was found to be more intense than reported positional isomeric tetrapropylporphycenes. The freebase porphycene exhibited moderate fluorescence and complexation ability with divalent metal ions, including Zn(II), which displayed an enhanced emission quantum yield (∼30%). The Pd(II) complex and freebase β-tetrabromoporphycene generated singlet oxygen efficiently (75 and 51%, respectively) and, hence, may find application as potential photosensitizers in photodynamic therapy. |
| doi_str_mv | 10.1021/acs.joc.1c02652 |
| format | Article |
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The substituent effect was found to be more intense than reported positional isomeric tetrapropylporphycenes. The freebase porphycene exhibited moderate fluorescence and complexation ability with divalent metal ions, including Zn(II), which displayed an enhanced emission quantum yield (∼30%). 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The Pd(II) complex and freebase β-tetrabromoporphycene generated singlet oxygen efficiently (75 and 51%, respectively) and, hence, may find application as potential photosensitizers in photodynamic therapy.</description><subject>Fluorescence</subject><subject>Halogenation</subject><subject>Photochemotherapy</subject><subject>Photosensitizing Agents</subject><subject>Singlet Oxygen</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kM9LwzAUx4Mobk7P3qRHwXbLjyZtvclQJwwEN88hTRPX0TY1acH-98Z1evNdHrz3eV8eHwCuEZwjiNFCSDffGzlHEmJG8QmYIophxDIYn4IphBhHBDMyARfO7aEvSuk5mBAKGSIZm4INCVmISIhYtFWdFa017VC1xra7QapG3QdvoitNI6pgMzTdTrnShcHS1G2lvg6bMBBNEaxEZT5Uc5hcgjMtKqeujn0G3p8et8tVtH59flk-rCNBCOmilCZJipiAMY4LISTNmcwKQjXLMp0QAlkRJyJLEswyhmjMtM4RLARKUa60TMkM3I65_unPXrmO16WTqqpEo0zvOGYY4xR6GR5djKi0xjmrNG9tWQs7cAT5j0nuTXJvkh9N-oubY3if16r443_VeeBuBMbL3npH7t-4b4opfQE</recordid><startdate>20220304</startdate><enddate>20220304</enddate><creator>Nagamaiah, Jodukathula</creator><creator>Dutta, Arnab</creator><creator>Pati, Narendra Nath</creator><creator>Sahoo, Sameeta</creator><creator>Soman, Rahul</creator><creator>Panda, Pradeepta K</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><orcidid>https://orcid.org/0000-0002-3177-2885</orcidid><orcidid>https://orcid.org/0000-0002-3243-5071</orcidid></search><sort><creationdate>20220304</creationdate><title>3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation</title><author>Nagamaiah, Jodukathula ; Dutta, Arnab ; Pati, Narendra Nath ; Sahoo, Sameeta ; Soman, Rahul ; Panda, Pradeepta K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-8577816a0424daac5b6c9d35f699f73306d47a97726961546ffb10da181befc83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Fluorescence</topic><topic>Halogenation</topic><topic>Photochemotherapy</topic><topic>Photosensitizing Agents</topic><topic>Singlet Oxygen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagamaiah, Jodukathula</creatorcontrib><creatorcontrib>Dutta, Arnab</creatorcontrib><creatorcontrib>Pati, Narendra Nath</creatorcontrib><creatorcontrib>Sahoo, Sameeta</creatorcontrib><creatorcontrib>Soman, Rahul</creatorcontrib><creatorcontrib>Panda, Pradeepta K</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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nagamaiah, Jodukathula</au><au>Dutta, Arnab</au><au>Pati, Narendra Nath</au><au>Sahoo, Sameeta</au><au>Soman, Rahul</au><au>Panda, Pradeepta K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2022-03-04</date><risdate>2022</risdate><volume>87</volume><issue>5</issue><spage>2721</spage><epage>2729</epage><pages>2721-2729</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>We have designed and synthesized 3,6,13,16-tetrapropylporphycene for the first time as its alkyl analogue from ethyl 4-propyl-1H-pyrrole-2-carboxylate. The substituent effect was found to be more intense than reported positional isomeric tetrapropylporphycenes. The freebase porphycene exhibited moderate fluorescence and complexation ability with divalent metal ions, including Zn(II), which displayed an enhanced emission quantum yield (∼30%). 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| source | ACS Publications; MEDLINE |
| subjects | Fluorescence Halogenation Photochemotherapy Photosensitizing Agents Singlet Oxygen |
| title | 3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation |
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