{"id":41,"date":"2016-08-02T15:06:13","date_gmt":"2016-08-02T15:06:13","guid":{"rendered":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/?page_id=41"},"modified":"2025-04-15T09:14:46","modified_gmt":"2025-04-15T14:14:46","slug":"methano10annulene","status":"publish","type":"page","link":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/methano10annulene\/","title":{"rendered":"Methano[10]annulene"},"content":{"rendered":"

Unusual H\u00fcckel aromatics have garnered interest in the field of material science due to their interesting structural and electronic characteristics. 1,6-methano[10]annulene (M10A) is one such unusual non-benzenoid aromatic and has been studied extensively in our lab. The bridged and non-planar structure of M10A results in amorphous semiconducting material when incorporated into donor-acceptor polymers. These materials have been used to prepare organic field-effect transistors, organic photovoltaics, and thermoelectric devices. Previous work with M10A-based polymers investigated the ability of the non-planar annulene to influence torsional strain along the polymer backbone arising from alkyl chain-aromatic ring interactions. Other studies on the material tested the utility of M10A-based amorphous conjugated polymers in all-organic and hybrid organic-inorganic thermoelectric devices with a variety of dopants and nano-structures to optimize thermopower and conductivity.<\/p>\n

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More recent research has focused on tuning the spin properties of the compound, through the synthesis of quinoidal derivatives of M10A molecules with extended conjugation. This quinoidal compound has a tendency to restore aromaticity by forming diradical species. The spin states of this diradical could be influenced by the nature of the H\u00fcckel-like or M\u00f6bius-like aromaticity within the annulene subunit.<\/p>\n

\"Baird<\/a><\/p>\n

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Project Publications<\/h4>\n

B. C. Streifel, J. L. Zafra, G. L. Espejo, C. J. G\u00f3mez-Garc\u00eda, J. Casado and J. D. Tovar, \u201cAn unusually small singlet-triplet gap in a quinoidal 1,6-methano[10]annulene due to Baird\u2019s 4n pi-electron triplet stabilization,\u201d Angew. Chem. Int. Ed., 2015, 54, 5888-5893 (inside cover article). DOI: 10.1002\/anie.201500879<\/a><\/p>\n

B. C. Streifel, J. F. Martinez-Hardigree, H. E. Katz, and J. D. Tovar, \u201cHeteroaromatic variation in amorphous 1,6-methano[10]annulene-based charge-transporting organic semiconductors,\u201d J. Mater. Chem. C., 2014, 2, 7851-7858. DOI: 10.1039\/C4TC01326C<\/a><\/p>\n

B. C. Streifel, P. A. Peart, J. F. Martinez-Hardigree, H. E. Katz and J. D. Tovar, “Torsional influences within disordered organic electronic materials based upon non-benzenoid 1,6- methano[10]annulene rings,” Macromolecules, 2012, 45, 7339-7349. DOI: 10.1021\/ma301408w<\/a><\/p>\n

G. A. Elbaz, L. M. Repka and J. D. Tovar, “Influence of annulene ratio on the electrochemical and spectroscopic properties of methano[10]annulene-thiophene random copolymers,” in ACS Applied Materials & Interfaces, 2011 (3) 2551-2556. DOI: 10.1021\/am200409b<\/a><\/p>\n

Peart, P. A.; Elbaz, G.; Tovar, J. D. \u201cOptical and electrical properties of pi-conjugated polymers built with the 10 pi-electron methano[10]annulene ring system,\u201d Pure Appl. Chem., 2010, 82 (4), 1045-1053. DOI: 10.1351\/PAC-CON-09-10-05<\/p>\n

Peart, P. A.; Tovar, J. D. “Expanding the realm of furan-based conducting polymers through conjugation with 1,6-methano[10]annulene,” Macromolecules, 2009, 42 (13), 4449-4455. DOI: 10.1021\/ma9006494<\/a><\/p>\n

Peart, P. A.; Repka, L. M.; Tovar, J. D. \u201cEmerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene.\u201d Eur. J. Org. Chem. 2008, 2193\u20132206. DOI: 10.1002\/ejoc.200800533<\/a><\/p>\n

Peart, P. A.; Tovar, J. D. \u201cMethano[10]annulene revisited: extended delocalization through conjugated polymers bearing larger H\u00fcckel aromatics.\u201d Org. Lett. 2007, 9 (16), 3041-4. DOI: 10.1021\/ol071062y<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

Unusual H\u00fcckel aromatics have garnered interest in the field of material science due to their interesting structural and electronic characteristics. 1,6-methano[10]annulene (M10A) is one such unusual non-benzenoid aromatic and has been studied extensively in our lab. The bridged and non-planar structure of M10A results in amorphous semiconducting material when incorporated into donor-acceptor polymers. These materials […]<\/p>\n","protected":false},"author":40,"featured_media":0,"parent":0,"menu_order":2,"comment_status":"closed","ping_status":"closed","template":"","meta":{"_acf_changed":false,"footnotes":""},"class_list":["post-41","page","type-page","status-publish","hentry"],"acf":[],"_links":{"self":[{"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/pages\/41","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/users\/40"}],"replies":[{"embeddable":true,"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/comments?post=41"}],"version-history":[{"count":3,"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/pages\/41\/revisions"}],"predecessor-version":[{"id":507,"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/pages\/41\/revisions\/507"}],"wp:attachment":[{"href":"https:\/\/sites.krieger.jhu.edu\/tovar-group\/wp-json\/wp\/v2\/media?parent=41"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}