Double head-to-tail direct arylation as a viable strategy towards the synthesis of the aza-analog of dihydrocyclopenta[]aceanthrylene - an intriguing antiaromatic heterocycle
The first case of double head-to-tail direct arylation of aromatic compounds and the unusual photophysical properties of the resulting 2,2 a 1,5 b 1,7 -tetraazacyclopenta[ hi ]aceanthrylene are reported. This molecule, comprising of two imidazo[1,2- a ]pyridine units, is antiaromatic due to the chan...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (6), p.1262-1265 |
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| container_title | Chemical communications (Cambridge, England) |
| container_volume | 52 |
| creator | Firmansyah, Dikhi Deperasi ska, Irena Vakuliuk, Olena Banasiewicz, Marzena Tasior, Mariusz Makarewicz, Artur Cyra ski, Micha K Kozankiewicz, Boles aw Gryko, Daniel T |
| description | The first case of double head-to-tail direct arylation of aromatic compounds and the unusual photophysical properties of the resulting 2,2
a
1,5
b
1,7
-tetraazacyclopenta[
hi
]aceanthrylene are reported. This molecule, comprising of two imidazo[1,2-
a
]pyridine units, is antiaromatic due to the changes in the efficiency of π-electron ring current and it belongs to a class of seldom encountered compounds with a dark lowest electronically excited singlet state.
Straightforwardly prepared head-to-tail bis-imidazo[1,2-
a
]pyridine displays antiaromaticity and no fluorescence. |
| doi_str_mv | 10.1039/c5cc08716c |
| format | Article |
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b
1,7
-tetraazacyclopenta[
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a
]pyridine units, is antiaromatic due to the changes in the efficiency of π-electron ring current and it belongs to a class of seldom encountered compounds with a dark lowest electronically excited singlet state.
Straightforwardly prepared head-to-tail bis-imidazo[1,2-
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]pyridine displays antiaromaticity and no fluorescence.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c5cc08716c</identifier><identifier>PMID: 26612424</identifier><language>eng</language><publisher>England</publisher><subject>Aromatic compounds ; Dark current ; Excitation ; Ring currents ; Strategy ; Synthesis</subject><ispartof>Chemical communications (Cambridge, England), 2016-01, Vol.52 (6), p.1262-1265</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c408t-19a5c5a871eea545072845dd44108a513d07d967db3c2103ecb9a4fc4b56f3893</citedby><cites>FETCH-LOGICAL-c408t-19a5c5a871eea545072845dd44108a513d07d967db3c2103ecb9a4fc4b56f3893</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26612424$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Firmansyah, Dikhi</creatorcontrib><creatorcontrib>Deperasi ska, Irena</creatorcontrib><creatorcontrib>Vakuliuk, Olena</creatorcontrib><creatorcontrib>Banasiewicz, Marzena</creatorcontrib><creatorcontrib>Tasior, Mariusz</creatorcontrib><creatorcontrib>Makarewicz, Artur</creatorcontrib><creatorcontrib>Cyra ski, Micha K</creatorcontrib><creatorcontrib>Kozankiewicz, Boles aw</creatorcontrib><creatorcontrib>Gryko, Daniel T</creatorcontrib><title>Double head-to-tail direct arylation as a viable strategy towards the synthesis of the aza-analog of dihydrocyclopenta[]aceanthrylene - an intriguing antiaromatic heterocycle</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The first case of double head-to-tail direct arylation of aromatic compounds and the unusual photophysical properties of the resulting 2,2
a
1,5
b
1,7
-tetraazacyclopenta[
hi
]aceanthrylene are reported. This molecule, comprising of two imidazo[1,2-
a
]pyridine units, is antiaromatic due to the changes in the efficiency of π-electron ring current and it belongs to a class of seldom encountered compounds with a dark lowest electronically excited singlet state.
Straightforwardly prepared head-to-tail bis-imidazo[1,2-
a
]pyridine displays antiaromaticity and no fluorescence.</description><subject>Aromatic compounds</subject><subject>Dark current</subject><subject>Excitation</subject><subject>Ring currents</subject><subject>Strategy</subject><subject>Synthesis</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkk1v1DAQhiNERUvhwh3kI0Iy2LGdOEeU8iVV4lIkJISiiT3ZNcrai-2A0h_Fb6y3W8oRX8Z-_cyM9Y6r6hlnrzkT3RujjGG65Y15UJ1x0UiqpP768LBXHW2FVKfV45R-sLK40o-q07ppeC1reVb9uQjLOCPZIliaA83gZmJdRJMJxHWG7IInkAiQXw4OZMoRMm5WksNviDaRvC3i6ktILpEw3QpwDRQ8zGFzUKzbrjYGs5o57NFn-PYdDELJKS3QI6EEPHE-R7dZnN-UU3YQw660N-VtGY_J-KQ6mWBO-PQunldf3r-76j_Sy88fPvVvL6mRTGfKO1BGQfEEEZRUrK21VNZKyZkGxYVlre2a1o7C1MVDNGMHcjJyVM0kdCfOq5fHuvsYfi6Y8rBzyeA8g8ewpIFrxmTbNkL_H22VZJ2Qui7oqyNqYkgp4jTso9sVmwfOhsMoh171_e0o-wK_uKu7jDu09-jf2RXg-RGIydzf_vsL4gbvcabY</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Firmansyah, Dikhi</creator><creator>Deperasi ska, Irena</creator><creator>Vakuliuk, Olena</creator><creator>Banasiewicz, Marzena</creator><creator>Tasior, Mariusz</creator><creator>Makarewicz, Artur</creator><creator>Cyra ski, Micha K</creator><creator>Kozankiewicz, Boles aw</creator><creator>Gryko, Daniel T</creator><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>20160101</creationdate><title>Double head-to-tail direct arylation as a viable strategy towards the synthesis of the aza-analog of dihydrocyclopenta[]aceanthrylene - an intriguing antiaromatic heterocycle</title><author>Firmansyah, Dikhi ; Deperasi ska, Irena ; Vakuliuk, Olena ; Banasiewicz, Marzena ; Tasior, Mariusz ; Makarewicz, Artur ; Cyra ski, Micha K ; Kozankiewicz, Boles aw ; Gryko, Daniel T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c408t-19a5c5a871eea545072845dd44108a513d07d967db3c2103ecb9a4fc4b56f3893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Aromatic compounds</topic><topic>Dark current</topic><topic>Excitation</topic><topic>Ring currents</topic><topic>Strategy</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Firmansyah, Dikhi</creatorcontrib><creatorcontrib>Deperasi ska, Irena</creatorcontrib><creatorcontrib>Vakuliuk, Olena</creatorcontrib><creatorcontrib>Banasiewicz, Marzena</creatorcontrib><creatorcontrib>Tasior, Mariusz</creatorcontrib><creatorcontrib>Makarewicz, Artur</creatorcontrib><creatorcontrib>Cyra ski, Micha K</creatorcontrib><creatorcontrib>Kozankiewicz, Boles aw</creatorcontrib><creatorcontrib>Gryko, Daniel T</creatorcontrib><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>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Firmansyah, Dikhi</au><au>Deperasi ska, Irena</au><au>Vakuliuk, Olena</au><au>Banasiewicz, Marzena</au><au>Tasior, Mariusz</au><au>Makarewicz, Artur</au><au>Cyra ski, Micha K</au><au>Kozankiewicz, Boles aw</au><au>Gryko, Daniel T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Double head-to-tail direct arylation as a viable strategy towards the synthesis of the aza-analog of dihydrocyclopenta[]aceanthrylene - an intriguing antiaromatic heterocycle</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2016-01-01</date><risdate>2016</risdate><volume>52</volume><issue>6</issue><spage>1262</spage><epage>1265</epage><pages>1262-1265</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The first case of double head-to-tail direct arylation of aromatic compounds and the unusual photophysical properties of the resulting 2,2
a
1,5
b
1,7
-tetraazacyclopenta[
hi
]aceanthrylene are reported. This molecule, comprising of two imidazo[1,2-
a
]pyridine units, is antiaromatic due to the changes in the efficiency of π-electron ring current and it belongs to a class of seldom encountered compounds with a dark lowest electronically excited singlet state.
Straightforwardly prepared head-to-tail bis-imidazo[1,2-
a
]pyridine displays antiaromaticity and no fluorescence.</abstract><cop>England</cop><pmid>26612424</pmid><doi>10.1039/c5cc08716c</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2016-01, Vol.52 (6), p.1262-1265 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_rsc_primary_c5cc08716c |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aromatic compounds Dark current Excitation Ring currents Strategy Synthesis |
| title | Double head-to-tail direct arylation as a viable strategy towards the synthesis of the aza-analog of dihydrocyclopenta[]aceanthrylene - an intriguing antiaromatic heterocycle |
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