{"id":"https://openalex.org/W2999349382","doi":"https://doi.org/10.1021/acs.joc.9b03308","title":"Interplay of Biradicaloid Character and Singlet/Triplet Energy Splitting for cis-/trans-Diindenoacenes and Related Benzothiophene-Capped Oligomers as Revealed by Extended Multireference Calculations","display_name":"Interplay of Biradicaloid Character and Singlet/Triplet Energy Splitting for cis-/trans-Diindenoacenes and Related Benzothiophene-Capped Oligomers as Revealed by Extended Multireference Calculations","publication_year":2020,"publication_date":"2020-01-17","ids":{"openalex":"https://openalex.org/W2999349382","doi":"https://doi.org/10.1021/acs.joc.9b03308","mag":"2999349382","pmid":"https://pubmed.ncbi.nlm.nih.gov/31948232"},"language":"en","primary_location":{"id":"doi:10.1021/acs.joc.9b03308","doi":"https://doi.org/10.1021/acs.joc.9b03308","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.9b03308","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"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/A5069314713","display_name":"Reed Nieman","orcid":"https://orcid.org/0000-0003-3011-5223","observed_orcids":["https://orcid.org/0000-0003-3011-5223"]},"institutions":[{"id":"https://openalex.org/I12315562","display_name":"Texas Tech University","ror":"https://ror.org/0405mnx93","country_code":"US","type":"education","lineage":["https://openalex.org/I12315562"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Reed Nieman","raw_affiliation_strings":["Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States","institution_ids":["https://openalex.org/I12315562"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5001196680","display_name":"Nadeesha J. Silva","orcid":"https://orcid.org/0000-0002-2845-7825","observed_orcids":["https://orcid.org/0000-0002-2845-7825"]},"institutions":[{"id":"https://openalex.org/I12315562","display_name":"Texas Tech University","ror":"https://ror.org/0405mnx93","country_code":"US","type":"education","lineage":["https://openalex.org/I12315562"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Nadeesha J. Silva","raw_affiliation_strings":["Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States"],"raw_orcid":"https://orcid.org/0000-0002-2845-7825","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States","institution_ids":["https://openalex.org/I12315562"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5066474261","display_name":"Ad\u00e9lia J. A. Aquino","orcid":"https://orcid.org/0000-0003-4891-6512","observed_orcids":["https://orcid.org/0000-0003-4891-6512"]},"institutions":[{"id":"https://openalex.org/I12315562","display_name":"Texas Tech University","ror":"https://ror.org/0405mnx93","country_code":"US","type":"education","lineage":["https://openalex.org/I12315562"]},{"id":"https://openalex.org/I162868743","display_name":"Tianjin University","ror":"https://ror.org/012tb2g32","country_code":"CN","type":"education","lineage":["https://openalex.org/I162868743"]}],"countries":["CN","US"],"is_corresponding":false,"raw_author_name":"Adelia J. A. Aquino","raw_affiliation_strings":["Department of Mechanical Engineering, Texas Tech University, Lubbock, Texas 79409, United States","School of Pharmaceutical Sciences and Technology, Tianjin University, Tianjin 300072, P. R. China"],"raw_orcid":"https://orcid.org/0000-0003-4891-6512","affiliations":[{"raw_affiliation_string":"Department of Mechanical Engineering, Texas Tech University, Lubbock, Texas 79409, United States","institution_ids":["https://openalex.org/I12315562"]},{"raw_affiliation_string":"School of Pharmaceutical Sciences and Technology, Tianjin University, Tianjin 300072, P. R. China","institution_ids":["https://openalex.org/I162868743"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5031639651","display_name":"Michael M. Haley","orcid":"https://orcid.org/0000-0002-7027-4141","observed_orcids":["https://orcid.org/0000-0002-7027-4141"]},"institutions":[{"id":"https://openalex.org/I181233156","display_name":"University of Oregon","ror":"https://ror.org/0293rh119","country_code":"US","type":"education","lineage":["https://openalex.org/I181233156"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Michael M. Haley","raw_affiliation_strings":["Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403, United States"],"raw_orcid":"https://orcid.org/0000-0002-7027-4141","affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403, United States","institution_ids":["https://openalex.org/I181233156"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5063314829","display_name":"Hans Lischka","orcid":"https://orcid.org/0000-0002-5656-3975","observed_orcids":["https://orcid.org/0000-0002-5656-3975"]},"institutions":[{"id":"https://openalex.org/I12315562","display_name":"Texas Tech University","ror":"https://ror.org/0405mnx93","country_code":"US","type":"education","lineage":["https://openalex.org/I12315562"]},{"id":"https://openalex.org/I162868743","display_name":"Tianjin University","ror":"https://ror.org/012tb2g32","country_code":"CN","type":"education","lineage":["https://openalex.org/I162868743"]}],"countries":["CN","US"],"is_corresponding":true,"raw_author_name":"Hans Lischka","raw_affiliation_strings":["Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States","School of Pharmaceutical Sciences and Technology, Tianjin University, Tianjin 300072, P. R. China"],"raw_orcid":"https://orcid.org/0000-0002-5656-3975","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States","institution_ids":["https://openalex.org/I12315562"]},{"raw_affiliation_string":"School of Pharmaceutical Sciences and Technology, Tianjin University, Tianjin 300072, P. R. China","institution_ids":["https://openalex.org/I162868743"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5063314829"],"corresponding_institution_ids":["https://openalex.org/I12315562","https://openalex.org/I162868743"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":1.4559,"has_fulltext":false,"cited_by_count":24,"citation_normalized_percentile":{"value":0.78177025,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":95,"max":98},"biblio":{"volume":"85","issue":"5","first_page":"3664","last_page":"3675"},"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":0.9970999956130981,"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":0.9970999956130981,"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/T10002","display_name":"Advanced Chemical Physics Studies","score":0.0010999999940395355,"subfield":{"id":"https://openalex.org/subfields/3107","display_name":"Atomic and Molecular Physics, and Optics"},"field":{"id":"https://openalex.org/fields/31","display_name":"Physics and Astronomy"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13253","display_name":"Chemical Reactions and Mechanisms","score":0.0003000000142492354,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical 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/singlet-triplet-energy-splitting","display_name":"singlet-triplet energy splitting","score":0.9419999718666077},{"id":"https://openalex.org/keywords/cis-trans-isomers","display_name":"cis-trans isomers","score":0.6679999828338623},{"id":"https://openalex.org/keywords/polycyclic-aromatic-hydrocarbons","display_name":"polycyclic aromatic hydrocarbons","score":0.9039999842643738},{"id":"https://openalex.org/keywords/unpaired-electron-density","display_name":"unpaired electron density","score":0.7789999842643738},{"id":"https://openalex.org/keywords/chemical-instability","display_name":"chemical instability","score":0.6990000009536743},{"id":"https://openalex.org/keywords/magneto-optical-materials","display_name":"magneto-optical materials","score":0.8939999938011169}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9247708916664124},{"id":"https://openalex.org/C186927785","wikidata":"https://www.wikidata.org/wiki/Q374793","display_name":"Unpaired electron","level":3,"score":0.8601521849632263},{"id":"https://openalex.org/C33062035","wikidata":"https://www.wikidata.org/wiki/Q3296863","display_name":"Singlet state","level":3,"score":0.7638782262802124},{"id":"https://openalex.org/C192386470","wikidata":"https://www.wikidata.org/wiki/Q210390","display_name":"Aromaticity","level":3,"score":0.7304418087005615},{"id":"https://openalex.org/C117633835","wikidata":"https://www.wikidata.org/wiki/Q5280165","display_name":"Diradical","level":4,"score":0.5470663905143738},{"id":"https://openalex.org/C2781442258","wikidata":"https://www.wikidata.org/wiki/Q46310","display_name":"Ab initio","level":2,"score":0.5313841700553894},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.4908497929573059},{"id":"https://openalex.org/C2779953032","wikidata":"https://www.wikidata.org/wiki/Q305364","display_name":"Thiophene","level":2,"score":0.44218456745147705},{"id":"https://openalex.org/C76766466","wikidata":"https://www.wikidata.org/wiki/Q3036629","display_name":"Triplet state","level":3,"score":0.42976683378219604},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.25347426533699036},{"id":"https://openalex.org/C181500209","wikidata":"https://www.wikidata.org/wiki/Q215328","display_name":"Excited state","level":2,"score":0.18570059537887573},{"id":"https://openalex.org/C184779094","wikidata":"https://www.wikidata.org/wiki/Q26383","display_name":"Atomic physics","level":1,"score":0.1771203875541687},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.0879688560962677},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/acs.joc.9b03308","doi":"https://doi.org/10.1021/acs.joc.9b03308","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.9b03308","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:31948232","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/31948232","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G7143427737","display_name":null,"funder_award_id":"CHE-1565780","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"}],"funders":[{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":84,"referenced_works":["https://openalex.org/W28713913","https://openalex.org/W1543882770","https://openalex.org/W1967032220","https://openalex.org/W1967206353","https://openalex.org/W1970152444","https://openalex.org/W1971275758","https://openalex.org/W1972703538","https://openalex.org/W1975708211","https://openalex.org/W1981745234","https://openalex.org/W1981872991","https://openalex.org/W1983196479","https://openalex.org/W1985894317","https://openalex.org/W1988091937","https://openalex.org/W1996618874","https://openalex.org/W1999351161","https://openalex.org/W1999387831","https://openalex.org/W2001417774","https://openalex.org/W2002299165","https://openalex.org/W2005510763","https://openalex.org/W2012400829","https://openalex.org/W2016688873","https://openalex.org/W2021060799","https://openalex.org/W2022747944","https://openalex.org/W2023339323","https://openalex.org/W2023792996","https://openalex.org/W2029095401","https://openalex.org/W2032003798","https://openalex.org/W2044151658","https://openalex.org/W2047721360","https://openalex.org/W2050123058","https://openalex.org/W2050177505","https://openalex.org/W2052567914","https://openalex.org/W2052573265","https://openalex.org/W2053337631","https://openalex.org/W2053520383","https://openalex.org/W2058363175","https://openalex.org/W2062226382","https://openalex.org/W2063170663","https://openalex.org/W2069785612","https://openalex.org/W2074019461","https://openalex.org/W2082069284","https://openalex.org/W2090777387","https://openalex.org/W2103561834","https://openalex.org/W2105050546","https://openalex.org/W2112453592","https://openalex.org/W2119547517","https://openalex.org/W2138441219","https://openalex.org/W2151562103","https://openalex.org/W2153955292","https://openalex.org/W2155751707","https://openalex.org/W2156467183","https://openalex.org/W2168247696","https://openalex.org/W2266459686","https://openalex.org/W2313724951","https://openalex.org/W2313904173","https://openalex.org/W2315426500","https://openalex.org/W2323615947","https://openalex.org/W2324049373","https://openalex.org/W2324384480","https://openalex.org/W2327751214","https://openalex.org/W2328602838","https://openalex.org/W2329118757","https://openalex.org/W2333668062","https://openalex.org/W2335483220","https://openalex.org/W2389596035","https://openalex.org/W2401046393","https://openalex.org/W2410151507","https://openalex.org/W2413570332","https://openalex.org/W2513823875","https://openalex.org/W2571285398","https://openalex.org/W2588478311","https://openalex.org/W2741815107","https://openalex.org/W2754729028","https://openalex.org/W2786634294","https://openalex.org/W2886375709","https://openalex.org/W2890727703","https://openalex.org/W2918140772","https://openalex.org/W2950216438","https://openalex.org/W2979928055","https://openalex.org/W2996904490","https://openalex.org/W4210962488","https://openalex.org/W4252171814","https://openalex.org/W4255270904","https://openalex.org/W4255350095"],"related_works":["https://openalex.org/W3036808484","https://openalex.org/W2007217726","https://openalex.org/W2890727703","https://openalex.org/W2401046393","https://openalex.org/W1977518824","https://openalex.org/W4244619282","https://openalex.org/W2074656237","https://openalex.org/W1974241476","https://openalex.org/W2050177873","https://openalex.org/W2009240161"],"abstract_inverted_index":{"The":[0,57,135,148],"biradicaloid":[1,91,142],"character":[2],"of":[3,6,18,31,52,68,83,93,114,131],"different":[4],"types":[5,39],"polycyclic":[7],"aromatic":[8],"hydrocarbons":[9],"is":[10],"an":[11],"important":[12],"quality":[13],"that":[14],"guides":[15],"the":[16,37,79,90,112,115,120,127,132,152,161,168,174,180],"development":[17],"new":[19],"materials":[20],"with":[21,108],"interesting":[22],"magneto-optical":[23],"properties.":[24],"Diindenoacene-based":[25],"systems":[26],"represent":[27],"such":[28],"a":[29,139],"class":[30],"promising":[32],"compounds.":[33],"In":[34],"this":[35],"work,":[36],"three":[38],"trans":[40,45,98,153],"-diindenoacenes,":[41,43],"cis":[42,136],"and":[44,78,124,172],"-dicyclopentaacenobis(benzothiophenes)":[46,154],"have":[47,85],"been":[48,86],"studied":[49],"by":[50],"means":[51],"advanced":[53],"ab":[54],"initio":[55],"methods.":[56],"descriptors":[58],"singlet/triplet":[59],"splitting":[60],"energy":[61],"(\u0394":[62],"E":[63,122],"S\u2013T":[64,123],"),":[65,74],"effective":[66],"number":[67],"unpaired":[69,75,162,175],"electrons":[70],"(":[71],"N":[72,128],"U":[73,129],"electron":[76,163,176],"density,":[77],"harmonic":[80],"oscillator":[81],"measure":[82],"aromaticity":[84],"used":[87],"to":[88,158],"characterize":[89],"properties":[92],"these":[94],"species.":[95],"For":[96],"all":[97],"structures,":[99],"low-spin":[100],"singlet":[101,133],"ground":[102],"states":[103],"were":[104,156],"found,":[105],"in":[106,151,179],"agreement":[107],"previous":[109],"investigations.":[110],"Increasing":[111],"length":[113],"inner":[116],"acene":[117],"chain":[118],"decreased":[119],"\u0394":[121],"strongly":[125],"increased":[126,141],"values":[130],"state.":[134],"-diindenoacenes":[137],"displayed":[138],"greatly":[140],"character,":[143],"indicating":[144],"enhanced":[145],"chemical":[146],"instability.":[147],"thiophene":[149],"rings":[150,171],"structures":[155],"found":[157,178],"simultaneously":[159],"restrict":[160],"density":[164,177],"from":[165],"extending":[166],"into":[167],"terminal":[169],"six-membered":[170],"confine":[173],"core":[181],"benzene":[182],"rings.":[183]},"counts_by_year":[{"year":2025,"cited_by_count":5},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":3},{"year":2021,"cited_by_count":4},{"year":2020,"cited_by_count":4}],"updated_date":"2026-10-16T09:59:22.235173","created_date":"2020-01-23T00:00:00"}
