Hexaethylsubporphyrins: β-alkyl analogues in the subporphyrin family
Two new subporphyrins were synthesized for the first time from a β-substituted pyrrole i.e. 3,4-diethylpyrrole via pyridine-tri-N-(3,4-diethylpyrrolyl)borane as building blocks. These β-hexaethylsubporphyrins are true contracted congeners of β-octaethylporphyrin (OEP). While the meso-triphenyl deriv...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2015-01, Vol.44 (46), p.19966-19973 |
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| container_end_page | 19973 |
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| container_issue | 46 |
| container_start_page | 19966 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 44 |
| creator | Chandra, Brijesh Kumar, B Sathish Mondal, Navendu Samanta, Anunay Panda, Pradeepta K |
| description | Two new subporphyrins were synthesized for the first time from a β-substituted pyrrole i.e. 3,4-diethylpyrrole via pyridine-tri-N-(3,4-diethylpyrrolyl)borane as building blocks. These β-hexaethylsubporphyrins are true contracted congeners of β-octaethylporphyrin (OEP). While the meso-triphenyl derivative of hexaethylsubporphyrin could be synthesized by following the reported method, the meso-free analogue could only be synthesized by condensation with trioxane, in the presence of catalytic methanesulfonic acid. These contracted macrocycles display interesting absorption, and emission behaviour including substituent dependent S2 fluorescence owing to the presence of flexible electron donating ethyl groups at their β-positions. The optical response and ultrafast S2 state dynamics of these systems suggest that it may be possible to tune the properties of the subporphyrin to develop efficient systems for solar energy capture and conversion processes. |
| doi_str_mv | 10.1039/c5dt03864b |
| format | Article |
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These β-hexaethylsubporphyrins are true contracted congeners of β-octaethylporphyrin (OEP). While the meso-triphenyl derivative of hexaethylsubporphyrin could be synthesized by following the reported method, the meso-free analogue could only be synthesized by condensation with trioxane, in the presence of catalytic methanesulfonic acid. These contracted macrocycles display interesting absorption, and emission behaviour including substituent dependent S2 fluorescence owing to the presence of flexible electron donating ethyl groups at their β-positions. 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These β-hexaethylsubporphyrins are true contracted congeners of β-octaethylporphyrin (OEP). While the meso-triphenyl derivative of hexaethylsubporphyrin could be synthesized by following the reported method, the meso-free analogue could only be synthesized by condensation with trioxane, in the presence of catalytic methanesulfonic acid. These contracted macrocycles display interesting absorption, and emission behaviour including substituent dependent S2 fluorescence owing to the presence of flexible electron donating ethyl groups at their β-positions. The optical response and ultrafast S2 state dynamics of these systems suggest that it may be possible to tune the properties of the subporphyrin to develop efficient systems for solar energy capture and conversion processes.</description><subject>Absorption</subject><subject>Alkylation</subject><subject>Boranes - chemical synthesis</subject><subject>Boranes - chemistry</subject><subject>Condensation</subject><subject>Congeners</subject><subject>Conversion</subject><subject>Crystallography, X-Ray</subject><subject>Derivatives</subject><subject>Dynamical systems</subject><subject>Dynamics</subject><subject>Electrochemical Techniques</subject><subject>Models, Molecular</subject><subject>Optical properties</subject><subject>Porphyrins - chemical synthesis</subject><subject>Porphyrins - chemistry</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtKw0AUhgdRrFY3PoBkKUJ0LudMJu60VisU3NR1mEwnNjq5mEnAvJYP4jMZbS3u5CzO4fDx8_MRcsLoBaMivjS4bKlQEtIdcsAgisKYC9jd3lyOyKH3L5RyTpHvkxGXyIGhOCDTmX3Xtl31zndpXTX1qm_y0l8Fnx-hdq-9C3SpXfXcWR_kZdCubPAXDDJd5K4_InuZdt4eb_aYPN1NF5NZOH-8f5hcz0MjOG1DlAKMVBE1qLiSEQwtYGk4s2i4FYAoGY0tRcDUUG0gyyCFTA0_AKuZGJOzdW7dVG9DpTYpcm-sc7q0VecTpugwPELxPxoJFFyxWA3o-Ro1TeV9Y7OkbvJCN33CaPJtOJng7eLH8M0An25yu7Swyy36q1R8Ac5_dfw</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Chandra, Brijesh</creator><creator>Kumar, B Sathish</creator><creator>Mondal, Navendu</creator><creator>Samanta, Anunay</creator><creator>Panda, Pradeepta K</creator><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><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150101</creationdate><title>Hexaethylsubporphyrins: β-alkyl analogues in the subporphyrin family</title><author>Chandra, Brijesh ; Kumar, B Sathish ; Mondal, Navendu ; Samanta, Anunay ; Panda, Pradeepta K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-5634c6870c58286745244dc21e5c2e34556109e0545bc0ac4ff4b4f809e44ea13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Absorption</topic><topic>Alkylation</topic><topic>Boranes - chemical synthesis</topic><topic>Boranes - chemistry</topic><topic>Condensation</topic><topic>Congeners</topic><topic>Conversion</topic><topic>Crystallography, X-Ray</topic><topic>Derivatives</topic><topic>Dynamical systems</topic><topic>Dynamics</topic><topic>Electrochemical Techniques</topic><topic>Models, Molecular</topic><topic>Optical properties</topic><topic>Porphyrins - chemical synthesis</topic><topic>Porphyrins - chemistry</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chandra, Brijesh</creatorcontrib><creatorcontrib>Kumar, B Sathish</creatorcontrib><creatorcontrib>Mondal, Navendu</creatorcontrib><creatorcontrib>Samanta, Anunay</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><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chandra, Brijesh</au><au>Kumar, B Sathish</au><au>Mondal, Navendu</au><au>Samanta, Anunay</au><au>Panda, Pradeepta K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hexaethylsubporphyrins: β-alkyl analogues in the subporphyrin family</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2015-01-01</date><risdate>2015</risdate><volume>44</volume><issue>46</issue><spage>19966</spage><epage>19973</epage><pages>19966-19973</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Two new subporphyrins were synthesized for the first time from a β-substituted pyrrole i.e. 3,4-diethylpyrrole via pyridine-tri-N-(3,4-diethylpyrrolyl)borane as building blocks. These β-hexaethylsubporphyrins are true contracted congeners of β-octaethylporphyrin (OEP). While the meso-triphenyl derivative of hexaethylsubporphyrin could be synthesized by following the reported method, the meso-free analogue could only be synthesized by condensation with trioxane, in the presence of catalytic methanesulfonic acid. These contracted macrocycles display interesting absorption, and emission behaviour including substituent dependent S2 fluorescence owing to the presence of flexible electron donating ethyl groups at their β-positions. The optical response and ultrafast S2 state dynamics of these systems suggest that it may be possible to tune the properties of the subporphyrin to develop efficient systems for solar energy capture and conversion processes.</abstract><cop>England</cop><pmid>26524153</pmid><doi>10.1039/c5dt03864b</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2015-01, Vol.44 (46), p.19966-19973 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Absorption Alkylation Boranes - chemical synthesis Boranes - chemistry Condensation Congeners Conversion Crystallography, X-Ray Derivatives Dynamical systems Dynamics Electrochemical Techniques Models, Molecular Optical properties Porphyrins - chemical synthesis Porphyrins - chemistry Pyridines - chemical synthesis Pyridines - chemistry |
| title | Hexaethylsubporphyrins: β-alkyl analogues in the subporphyrin family |
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