{"id":"https://openalex.org/W1982957864","doi":"https://doi.org/10.1246/bcsj.20110286","title":"Trimethylsumanene: Enantioselective Synthesis, Substituent Effect on Bowl Structure, Inversion Energy, and Electron Conductivity","display_name":"Trimethylsumanene: Enantioselective Synthesis, Substituent Effect on Bowl Structure, Inversion Energy, and Electron Conductivity","publication_year":2012,"publication_date":"2012-03-28","ids":{"openalex":"https://openalex.org/W1982957864","doi":"https://doi.org/10.1246/bcsj.20110286","mag":"1982957864"},"language":"en","primary_location":{"id":"doi:10.1246/bcsj.20110286","doi":"https://doi.org/10.1246/bcsj.20110286","is_oa":false,"landing_page_url":"https://doi.org/10.1246/bcsj.20110286","pdf_url":null,"source":{"id":"https://openalex.org/S95305481","display_name":"Bulletin of the Chemical Society of Japan","issn_l":"0009-2673","issn":["0009-2673","1348-0634"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","norway-1","poland-100","russia-white-list-1"],"host_organization":"https://openalex.org/P4310311648","host_organization_name":"Oxford University Press","host_organization_lineage":["https://openalex.org/P4310311648","https://openalex.org/P4310311647"],"host_organization_lineage_names":["Oxford University Press","University of Oxford"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Bulletin of the Chemical Society of Japan","raw_type":"journal-article"},"parent_works":[],"lineage":["https://openalex.org/W1982957864"],"child_works_count":0,"type":"article","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5011874515","display_name":"Shuhei Higashibayashi","orcid":"https://orcid.org/0000-0002-2957-461X","observed_orcids":["https://orcid.org/0000-0002-2957-461X"]},"institutions":[{"id":"https://openalex.org/I4210143791","display_name":"Institute for Molecular Science","ror":"https://ror.org/04wqh5h97","country_code":"JP","type":"facility","lineage":["https://openalex.org/I1319490839","https://openalex.org/I199525922","https://openalex.org/I4210143791"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Shuhei Higashibayashi","raw_affiliation_strings":["Research Center for Molecular Scale Nanoscience, Institute for Molecular Science"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Research Center for Molecular Scale Nanoscience, Institute for Molecular Science","institution_ids":["https://openalex.org/I4210143791"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5016860789","display_name":"Ryoji Tsuruoka","orcid":"https://orcid.org/0000-0003-3748-9172","observed_orcids":["https://orcid.org/0000-0003-3748-9172"]},"institutions":[{"id":"https://openalex.org/I4210143791","display_name":"Institute for Molecular Science","ror":"https://ror.org/04wqh5h97","country_code":"JP","type":"facility","lineage":["https://openalex.org/I1319490839","https://openalex.org/I199525922","https://openalex.org/I4210143791"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Ryoji Tsuruoka","raw_affiliation_strings":["Research Center for Molecular Scale Nanoscience, Institute for Molecular Science"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Research Center for Molecular Scale Nanoscience, Institute for Molecular Science","institution_ids":["https://openalex.org/I4210143791"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5057905338","display_name":"Yarasi Soujanya","orcid":"https://orcid.org/0000-0003-4369-0753","observed_orcids":["https://orcid.org/0000-0003-4369-0753"]},"institutions":[{"id":"https://openalex.org/I55664587","display_name":"Indian Institute of Chemical Technology","ror":"https://ror.org/040dky007","country_code":"IN","type":"facility","lineage":["https://openalex.org/I2799351866","https://openalex.org/I4210134808","https://openalex.org/I55664587","https://openalex.org/I66760702"]}],"countries":["IN"],"is_corresponding":false,"raw_author_name":"Yarasi Soujanya","raw_affiliation_strings":["Molecular Modeling Group, Indian Institute of Chemical Technology"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Molecular Modeling Group, Indian Institute of Chemical Technology","institution_ids":["https://openalex.org/I55664587"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5034583426","display_name":"Uppula Purushotham","orcid":"https://orcid.org/0000-0002-1808-1772","observed_orcids":["https://orcid.org/0000-0002-1808-1772"]},"institutions":[{"id":"https://openalex.org/I55664587","display_name":"Indian Institute of Chemical Technology","ror":"https://ror.org/040dky007","country_code":"IN","type":"facility","lineage":["https://openalex.org/I2799351866","https://openalex.org/I4210134808","https://openalex.org/I55664587","https://openalex.org/I66760702"]}],"countries":["IN"],"is_corresponding":false,"raw_author_name":"Uppula Purushotham","raw_affiliation_strings":["Molecular Modeling Group, Indian Institute of Chemical Technology"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Molecular Modeling Group, Indian Institute of Chemical Technology","institution_ids":["https://openalex.org/I55664587"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5042534009","display_name":"Garikapati Narahari Sastry","orcid":"https://orcid.org/0000-0003-3181-7673","observed_orcids":["https://orcid.org/0000-0003-3181-7673"]},"institutions":[{"id":"https://openalex.org/I55664587","display_name":"Indian Institute of Chemical Technology","ror":"https://ror.org/040dky007","country_code":"IN","type":"facility","lineage":["https://openalex.org/I2799351866","https://openalex.org/I4210134808","https://openalex.org/I55664587","https://openalex.org/I66760702"]}],"countries":["IN"],"is_corresponding":false,"raw_author_name":"G Narahari Sastry","raw_affiliation_strings":["Molecular Modeling Group, Indian Institute of Chemical Technology"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Molecular Modeling Group, Indian Institute of Chemical Technology","institution_ids":["https://openalex.org/I55664587"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5045506489","display_name":"Shu Seki","orcid":"https://orcid.org/0000-0001-7851-4405","observed_orcids":["https://orcid.org/0000-0001-7851-4405"]},"institutions":[{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Shu Seki","raw_affiliation_strings":["Department of Applied Chemistry, Graduate School of Engineering, Osaka University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Applied Chemistry, Graduate School of Engineering, Osaka University","institution_ids":["https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5051765004","display_name":"Takeharu Ishikawa","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I136446963","display_name":"Okayama University of Science","ror":"https://ror.org/05aevyc10","country_code":"JP","type":"education","lineage":["https://openalex.org/I136446963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Takeharu Ishikawa","raw_affiliation_strings":["Department of Chemistry, Faculty of Science, Okayama University of Science"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Faculty of Science, Okayama University of Science","institution_ids":["https://openalex.org/I136446963"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5062534701","display_name":"Shinji Toyota","orcid":"https://orcid.org/0000-0002-1504-2030","observed_orcids":["https://orcid.org/0000-0002-1504-2030"]},"institutions":[{"id":"https://openalex.org/I136446963","display_name":"Okayama University of Science","ror":"https://ror.org/05aevyc10","country_code":"JP","type":"education","lineage":["https://openalex.org/I136446963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Shinji Toyota","raw_affiliation_strings":["Department of Chemistry, Faculty of Science, Okayama University of Science"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Faculty of Science, Okayama University of Science","institution_ids":["https://openalex.org/I136446963"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5065473510","display_name":"Hidehiro Sakurai","orcid":"https://orcid.org/0000-0001-5783-4151","observed_orcids":["https://orcid.org/0000-0001-5783-4151"]},"institutions":[{"id":"https://openalex.org/I4210143791","display_name":"Institute for Molecular Science","ror":"https://ror.org/04wqh5h97","country_code":"JP","type":"facility","lineage":["https://openalex.org/I1319490839","https://openalex.org/I199525922","https://openalex.org/I4210143791"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hidehiro Sakurai","raw_affiliation_strings":["Research Center for Molecular Scale Nanoscience, Institute for Molecular Science"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Research Center for Molecular Scale Nanoscience, Institute for Molecular Science","institution_ids":["https://openalex.org/I4210143791"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":4,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":305000,"currency":"JPY","value_usd":2040},"apc_paid":null,"fwci":5.3305,"has_fulltext":false,"cited_by_count":91,"citation_normalized_percentile":{"value":0.96625979,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"85","issue":"4","first_page":"450","last_page":"467"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11298","display_name":"Synthesis and Properties of Aromatic Compounds","score":0.9901999831199646,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T11298","display_name":"Synthesis and Properties of Aromatic Compounds","score":0.9901999831199646,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13115","display_name":"Axial and Atropisomeric Chirality Synthesis","score":0.004399999976158142,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10578","display_name":"Supramolecular Chemistry and Complexes","score":0.002400000113993883,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/sumanene","display_name":"sumanene","score":0.9679999947547913},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.9120000004768372},{"id":"https://openalex.org/keywords/substituent-effects","display_name":"substituent effects","score":0.8809999823570251},{"id":"https://openalex.org/keywords/methylation","display_name":"methylation","score":0.7549999952316284},{"id":"https://openalex.org/keywords/corannulene","display_name":"corannulene","score":0.8029999732971191},{"id":"https://openalex.org/keywords/steric-repulsion","display_name":"steric repulsion","score":0.7269999980926514},{"id":"https://openalex.org/keywords/c-hpi-interactions","display_name":"C-H\u22ef\u03c0 interactions","score":0.8420000076293945},{"id":"https://openalex.org/keywords/electrostatic-interactions","display_name":"electrostatic interactions","score":0.621999979019165},{"id":"https://openalex.org/keywords/electronic-conductivity","display_name":"electronic conductivity","score":0.6140000224113464},{"id":"https://openalex.org/keywords/time-resolved-microwave-conductivity","display_name":"time-resolved microwave conductivity","score":0.8539999723434448},{"id":"https://openalex.org/keywords/olefin-metathesis","display_name":"olefin metathesis","score":0.871999979019165},{"id":"https://openalex.org/keywords/oxidative-aromatization","display_name":"oxidative aromatization","score":0.8999999761581421},{"id":"https://openalex.org/keywords/chiral-hplc-resolution","display_name":"chiral HPLC resolution","score":0.7559999823570251}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.928500771522522},{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.670901894569397},{"id":"https://openalex.org/C201194858","wikidata":"https://www.wikidata.org/wiki/Q898238","display_name":"Steric effects","level":2,"score":0.6271543502807617},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.5060004591941833},{"id":"https://openalex.org/C2781314386","wikidata":"https://www.wikidata.org/wiki/Q417774","display_name":"Corannulene","level":3,"score":0.4606897830963135},{"id":"https://openalex.org/C486523","wikidata":"https://www.wikidata.org/wiki/Q494483","display_name":"Enantiomer","level":2,"score":0.42450982332229614},{"id":"https://openalex.org/C2778689049","wikidata":"https://www.wikidata.org/wiki/Q898422","display_name":"Substituent","level":2,"score":0.4130690097808838},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.40670228004455566},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3481696844100952},{"id":"https://openalex.org/C8010536","wikidata":"https://www.wikidata.org/wiki/Q160398","display_name":"Crystallography","level":1,"score":0.3397279381752014},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.23791968822479248},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.1487753987312317},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.13515713810920715}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1246/bcsj.20110286","doi":"https://doi.org/10.1246/bcsj.20110286","is_oa":false,"landing_page_url":"https://doi.org/10.1246/bcsj.20110286","pdf_url":null,"source":{"id":"https://openalex.org/S95305481","display_name":"Bulletin of the Chemical Society of Japan","issn_l":"0009-2673","issn":["0009-2673","1348-0634"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","norway-1","poland-100","russia-white-list-1"],"host_organization":"https://openalex.org/P4310311648","host_organization_name":"Oxford University Press","host_organization_lineage":["https://openalex.org/P4310311648","https://openalex.org/P4310311647"],"host_organization_lineage_names":["Oxford University Press","University of Oxford"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Bulletin of the Chemical Society of Japan","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G4826808535","display_name":"Synthesis and Properties of Functionalized Buckybowls","funder_award_id":"23350024","funder_id":"https://openalex.org/F4320334764","funder_display_name":"Japan Society for the Promotion of Science"}],"funders":[{"id":"https://openalex.org/F4320334764","display_name":"Japan Society for the Promotion of Science","ror":"https://ror.org/00hhkn466"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":68,"referenced_works":["https://openalex.org/W1963918202","https://openalex.org/W1965939584","https://openalex.org/W1968204244","https://openalex.org/W1974981081","https://openalex.org/W1975974249","https://openalex.org/W1978189691","https://openalex.org/W1979781584","https://openalex.org/W1983478371","https://openalex.org/W1983543113","https://openalex.org/W1989212121","https://openalex.org/W1990371724","https://openalex.org/W1995293745","https://openalex.org/W1998003598","https://openalex.org/W1998359358","https://openalex.org/W1998542414","https://openalex.org/W1999626873","https://openalex.org/W2000589521","https://openalex.org/W2002046721","https://openalex.org/W2006099558","https://openalex.org/W2013260690","https://openalex.org/W2018351873","https://openalex.org/W2023104034","https://openalex.org/W2028184840","https://openalex.org/W2029399759","https://openalex.org/W2030017594","https://openalex.org/W2030695520","https://openalex.org/W2030841140","https://openalex.org/W2031730820","https://openalex.org/W2032183911","https://openalex.org/W2033919028","https://openalex.org/W2034073732","https://openalex.org/W2034319207","https://openalex.org/W2036440385","https://openalex.org/W2040363845","https://openalex.org/W2041495909","https://openalex.org/W2045833065","https://openalex.org/W2050866245","https://openalex.org/W2056917541","https://openalex.org/W2061899554","https://openalex.org/W2065730920","https://openalex.org/W2067419100","https://openalex.org/W2069130383","https://openalex.org/W2069712216","https://openalex.org/W2074290222","https://openalex.org/W2078391242","https://openalex.org/W2079911278","https://openalex.org/W2080272266","https://openalex.org/W2088764599","https://openalex.org/W2093137710","https://openalex.org/W2097913943","https://openalex.org/W2105595130","https://openalex.org/W2112783175","https://openalex.org/W2122994460","https://openalex.org/W2125892656","https://openalex.org/W2131295166","https://openalex.org/W2131573649","https://openalex.org/W2143800154","https://openalex.org/W2147331773","https://openalex.org/W2154007291","https://openalex.org/W2156739932","https://openalex.org/W2157822062","https://openalex.org/W2158545510","https://openalex.org/W2158814401","https://openalex.org/W2165947618","https://openalex.org/W2165984168","https://openalex.org/W2326385719","https://openalex.org/W2331158180","https://openalex.org/W2950844313"],"related_works":["https://openalex.org/W1983478371","https://openalex.org/W3084439760","https://openalex.org/W2324375974","https://openalex.org/W2131542594","https://openalex.org/W2077658147","https://openalex.org/W2323165618","https://openalex.org/W2065730920","https://openalex.org/W1997010191","https://openalex.org/W2177217332","https://openalex.org/W2073296306"],"abstract_inverted_index":{"Abstract":[0],"C":[1],"3":[2],"symmetric":[3],"chiral":[4],"trimethylsumanene":[5,56,179],"was":[6,29,57,120,156,180],"enantioselectively":[7],"synthesized":[8],"through":[9],"Pd-catalyzed":[10],"syn-selective":[11],"cyclotrimerization":[12],"of":[13,38,53,93,96,105,128,137,167,172,178,190],"an":[14],"enantiomerically":[15],"pure":[16],"iodonorbornenone,":[17],"ring-opening/closing":[18],"olefin":[19],"metathesis,":[20],"and":[21,55,71,77,102,107,144,154,169],"oxidative":[22],"aromatization":[23],"where":[24],"the":[25,32,39,48,69,74,94,99,123,141,159,173],"sp3":[26],"stereogenic":[27],"center":[28],"transmitted":[30],"to":[31,61,68,82,90,111,122],"bowl":[33,75,100,124,160],"chirality.":[34],"Chiral":[35],"HPLC":[36],"analysis/resolution":[37],"derivatives":[40],"were":[41,80,109,147],"also":[42],"achieved.":[43],"Based":[44],"on":[45,84,98,140],"theoretical":[46,72],"calculations,":[47,153],"columnar":[49],"crystal":[50],"packing":[51],"structure":[52,101,143],"sumanene":[54,87,106,142],"interpreted":[58],"as":[59],"due":[60],"attractive":[62],"electrostatic":[63],"or":[64],"CH\u2013\u03c0":[65],"interaction.":[66],"According":[67],"experimental":[70],"studies,":[73],"depth":[76],"inversion":[78,103],"energy":[79,104,126,146],"found":[81],"increase":[83],"methylation":[85,97],"for":[86],"in":[88,113],"contrast":[89],"corannulene.":[91],"Dissimilarities":[92],"effect":[95],"corannulene":[108],"ascribed":[110],"differences":[112],"steric":[114,170],"repulsion.":[115],"A":[116],"double-well":[117],"potential":[118],"model":[119],"fitted":[121],"structure\u2013inversion":[125],"correlation":[127],"substituted":[129],"sumanenes,":[130],"with":[131,188],"a":[132,165],"small":[133],"deviation.":[134],"The":[135,175],"effects":[136,171],"various":[138],"substituents":[139],"bowl-inversion":[145],"analyzed":[148],"by":[149,164,182],"density":[150],"functional":[151],"theory":[152],"it":[155],"shown":[157],"that":[158,189],"rigidity":[161],"is":[162],"controlled":[163],"combination":[166],"electronic":[168],"substituents.":[174],"electron":[176],"conductivity":[177,185],"investigated":[181],"time-resolved":[183],"microwave":[184],"method,":[186],"compared":[187],"sumanene.":[191]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":4},{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":6},{"year":2021,"cited_by_count":5},{"year":2020,"cited_by_count":4},{"year":2019,"cited_by_count":3},{"year":2018,"cited_by_count":7},{"year":2017,"cited_by_count":10},{"year":2016,"cited_by_count":8},{"year":2015,"cited_by_count":8},{"year":2014,"cited_by_count":13},{"year":2013,"cited_by_count":11},{"year":2012,"cited_by_count":7}],"updated_date":"2026-11-10T11:39:43.021295","created_date":"2016-06-24T00:00:00"}
