Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility
Pyracylene is a unique cyclopenta‐fused polycyclic aromatic hydrocarbon (CP‐PAH) that exhibits dual aromatic characteristics. Herein we report the synthesis of doubly N‐doped benzannulated pyracylenes, namely dibenzodiazapyracylenes, by oxidative N−N linking reaction of [2.2](2,5)pyrrolophane‐type p...
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| Veröffentlicht in: | Angewandte Chemie 2022-03, Vol.134 (14), p.n/a |
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| container_title | Angewandte Chemie |
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| creator | Morimoto, Yuki Koo, Yun Hee Otsubo, Kazuya Kitakado, Hidetsugu Seki, Shu Osuka, Atsuhiro Tanaka, Takayuki |
| description | Pyracylene is a unique cyclopenta‐fused polycyclic aromatic hydrocarbon (CP‐PAH) that exhibits dual aromatic characteristics. Herein we report the synthesis of doubly N‐doped benzannulated pyracylenes, namely dibenzodiazapyracylenes, by oxidative N−N linking reaction of [2.2](2,5)pyrrolophane‐type precursors. Dibenzodiazapyracylenes displayed well‐ordered π‐stacked molecular packing in the solid state, which were feasible for effective hole‐transporting along the stacking direction. High carrier mobility was estimated by microwave conductivity measurements as compared to dibenzoullazine. The high HOMO level of dibenzodiazapyracylene was verified by electrochemistry and its persistent radical cation species has been detected.
A novel nitrogen‐doped CP‐PAH, dibenzodiazapyracylene, was successfully synthesized and characterized. The aromatic and antiaromatic resonance hybrid characters have been verified by comparing their 1H NMR spectra to those of reference molecules. Their condensed packing structures in the solid state allowed for the effective hole transporting. |
| doi_str_mv | 10.1002/ange.202200341 |
| format | Article |
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A novel nitrogen‐doped CP‐PAH, dibenzodiazapyracylene, was successfully synthesized and characterized. The aromatic and antiaromatic resonance hybrid characters have been verified by comparing their 1H NMR spectra to those of reference molecules. Their condensed packing structures in the solid state allowed for the effective hole transporting.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202200341</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Antiaromaticity ; Aromatic hydrocarbons ; Carrier mobility ; Chemistry ; Electrochemistry ; Hole-Transporting Materials ; Microwave Conductivity ; Mobility ; Polycyclic Aromatic Hydrocarbons ; Solid-State Emission</subject><ispartof>Angewandte Chemie, 2022-03, Vol.134 (14), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2461-b13cb9d8c027a6196cabd8c8e2a2b3fb712ed82df7ea3a2db4bdf9007df392433</citedby><cites>FETCH-LOGICAL-c2461-b13cb9d8c027a6196cabd8c8e2a2b3fb712ed82df7ea3a2db4bdf9007df392433</cites><orcidid>0000-0001-7851-4405 ; 0000-0001-8697-8488 ; 0000-0001-8018-7984</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.202200341$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.202200341$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Morimoto, Yuki</creatorcontrib><creatorcontrib>Koo, Yun Hee</creatorcontrib><creatorcontrib>Otsubo, Kazuya</creatorcontrib><creatorcontrib>Kitakado, Hidetsugu</creatorcontrib><creatorcontrib>Seki, Shu</creatorcontrib><creatorcontrib>Osuka, Atsuhiro</creatorcontrib><creatorcontrib>Tanaka, Takayuki</creatorcontrib><title>Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility</title><title>Angewandte Chemie</title><description>Pyracylene is a unique cyclopenta‐fused polycyclic aromatic hydrocarbon (CP‐PAH) that exhibits dual aromatic characteristics. Herein we report the synthesis of doubly N‐doped benzannulated pyracylenes, namely dibenzodiazapyracylenes, by oxidative N−N linking reaction of [2.2](2,5)pyrrolophane‐type precursors. Dibenzodiazapyracylenes displayed well‐ordered π‐stacked molecular packing in the solid state, which were feasible for effective hole‐transporting along the stacking direction. High carrier mobility was estimated by microwave conductivity measurements as compared to dibenzoullazine. The high HOMO level of dibenzodiazapyracylene was verified by electrochemistry and its persistent radical cation species has been detected.
A novel nitrogen‐doped CP‐PAH, dibenzodiazapyracylene, was successfully synthesized and characterized. The aromatic and antiaromatic resonance hybrid characters have been verified by comparing their 1H NMR spectra to those of reference molecules. Their condensed packing structures in the solid state allowed for the effective hole transporting.</description><subject>Antiaromaticity</subject><subject>Aromatic hydrocarbons</subject><subject>Carrier mobility</subject><subject>Chemistry</subject><subject>Electrochemistry</subject><subject>Hole-Transporting Materials</subject><subject>Microwave Conductivity</subject><subject>Mobility</subject><subject>Polycyclic Aromatic Hydrocarbons</subject><subject>Solid-State Emission</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAUhS0EEqWwMltiTvEjzYOt6hOpFIYyR36ldWXiYCeCdOIn8Bv5JbgqgpHp3nv0nXukA8A1RgOMELll1UYNCCIEIRrjE9DDQ4Ijmg7TU9BDKI6jjMT5ObjwfocQSkia90Az0VxVeys127O6c0x0RlXK38GJbbnp4Orr43NiayXhuBMmLFXDgjRrfZCerOlEkLWAD9Yo0Rrl4XrLGjh932quG7jQmy0cM-e0coHh2uimuwRnJTNeXf3MPnieTdfjRbR8nN-PR8tIkDjBEcdU8FxmApGUJThPBOPhyhRhhNOSp5gomRFZpopRRiSPuSxzhFJZ0pzElPbBzfFv7exrq3xT7GzrqhBZkCRG-fAABWpwpISz3jtVFrXTL8x1BUbFodni0Gzx22ww5EfDmzaq-4cuRqv59M_7DdGDgRk</recordid><startdate>20220328</startdate><enddate>20220328</enddate><creator>Morimoto, Yuki</creator><creator>Koo, Yun Hee</creator><creator>Otsubo, Kazuya</creator><creator>Kitakado, Hidetsugu</creator><creator>Seki, Shu</creator><creator>Osuka, Atsuhiro</creator><creator>Tanaka, Takayuki</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-7851-4405</orcidid><orcidid>https://orcid.org/0000-0001-8697-8488</orcidid><orcidid>https://orcid.org/0000-0001-8018-7984</orcidid></search><sort><creationdate>20220328</creationdate><title>Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility</title><author>Morimoto, Yuki ; Koo, Yun Hee ; Otsubo, Kazuya ; Kitakado, Hidetsugu ; Seki, Shu ; Osuka, Atsuhiro ; Tanaka, Takayuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2461-b13cb9d8c027a6196cabd8c8e2a2b3fb712ed82df7ea3a2db4bdf9007df392433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Antiaromaticity</topic><topic>Aromatic hydrocarbons</topic><topic>Carrier mobility</topic><topic>Chemistry</topic><topic>Electrochemistry</topic><topic>Hole-Transporting Materials</topic><topic>Microwave Conductivity</topic><topic>Mobility</topic><topic>Polycyclic Aromatic Hydrocarbons</topic><topic>Solid-State Emission</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morimoto, Yuki</creatorcontrib><creatorcontrib>Koo, Yun Hee</creatorcontrib><creatorcontrib>Otsubo, Kazuya</creatorcontrib><creatorcontrib>Kitakado, Hidetsugu</creatorcontrib><creatorcontrib>Seki, Shu</creatorcontrib><creatorcontrib>Osuka, Atsuhiro</creatorcontrib><creatorcontrib>Tanaka, Takayuki</creatorcontrib><collection>CrossRef</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>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morimoto, Yuki</au><au>Koo, Yun Hee</au><au>Otsubo, Kazuya</au><au>Kitakado, Hidetsugu</au><au>Seki, Shu</au><au>Osuka, Atsuhiro</au><au>Tanaka, Takayuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility</atitle><jtitle>Angewandte Chemie</jtitle><date>2022-03-28</date><risdate>2022</risdate><volume>134</volume><issue>14</issue><epage>n/a</epage><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Pyracylene is a unique cyclopenta‐fused polycyclic aromatic hydrocarbon (CP‐PAH) that exhibits dual aromatic characteristics. 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A novel nitrogen‐doped CP‐PAH, dibenzodiazapyracylene, was successfully synthesized and characterized. The aromatic and antiaromatic resonance hybrid characters have been verified by comparing their 1H NMR spectra to those of reference molecules. Their condensed packing structures in the solid state allowed for the effective hole transporting.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.202200341</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-7851-4405</orcidid><orcidid>https://orcid.org/0000-0001-8697-8488</orcidid><orcidid>https://orcid.org/0000-0001-8018-7984</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Antiaromaticity Aromatic hydrocarbons Carrier mobility Chemistry Electrochemistry Hole-Transporting Materials Microwave Conductivity Mobility Polycyclic Aromatic Hydrocarbons Solid-State Emission |
| title | Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility |
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