{"id":"https://openalex.org/W4372257684","doi":"https://doi.org/10.1002/chem.202301153","title":"Comparison of Antiaromatic Properties in a Series of Structurally Isomeric Naphthothiophene\u2010Fused s\u2010Indacenes","display_name":"Comparison of Antiaromatic Properties in a Series of Structurally Isomeric Naphthothiophene\u2010Fused s\u2010Indacenes","publication_year":2023,"publication_date":"2023-05-05","ids":{"openalex":"https://openalex.org/W4372257684","doi":"https://doi.org/10.1002/chem.202301153","pmid":"https://pubmed.ncbi.nlm.nih.gov/37146211"},"language":"en","primary_location":{"id":"doi:10.1002/chem.202301153","doi":"https://doi.org/10.1002/chem.202301153","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.202301153","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry \u2013 A European Journal","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/A5073957270","display_name":"Gabrielle I. Warren","orcid":"https://orcid.org/0000-0001-5971-9026","observed_orcids":["https://orcid.org/0000-0001-5971-9026"]},"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":"Gabrielle I. Warren","raw_affiliation_strings":["Department of Chemistry & Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA","Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253 USA"],"raw_orcid":"https://orcid.org/0000-0001-5971-9026","affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA","institution_ids":["https://openalex.org/I181233156"]},{"raw_affiliation_string":"Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253 USA","institution_ids":["https://openalex.org/I181233156"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5047756972","display_name":"Luca J. Zocchi","orcid":"https://orcid.org/0000-0001-9649-2764","observed_orcids":["https://orcid.org/0000-0001-9649-2764"]},"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":"Luca J. Zocchi","raw_affiliation_strings":["Department of Chemistry & Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA","Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253 USA"],"raw_orcid":"https://orcid.org/0000-0001-9649-2764","affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA","institution_ids":["https://openalex.org/I181233156"]},{"raw_affiliation_string":"Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253 USA","institution_ids":["https://openalex.org/I181233156"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5103119538","display_name":"Lev N. Zakharov","orcid":"https://orcid.org/0000-0003-3340-4645","observed_orcids":["https://orcid.org/0000-0003-3340-4645"]},"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":"Lev N. Zakharov","raw_affiliation_strings":["Center for Advanced Materials Characterization at Oregon (CAMCOR), University of Oregon, Eugene, Oregon, 97403-1433 USA"],"raw_orcid":"https://orcid.org/0000-0003-3340-4645","affiliations":[{"raw_affiliation_string":"Center for Advanced Materials Characterization at Oregon (CAMCOR), University of Oregon, Eugene, Oregon, 97403-1433 USA","institution_ids":["https://openalex.org/I181233156"]}]},{"author_position":"last","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":true,"raw_author_name":"Michael M. Haley","raw_affiliation_strings":["Department of Chemistry & Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA","Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253 USA"],"raw_orcid":"https://orcid.org/0000-0002-7027-4141","affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA","institution_ids":["https://openalex.org/I181233156"]},{"raw_affiliation_string":"Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253 USA","institution_ids":["https://openalex.org/I181233156"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5031639651"],"corresponding_institution_ids":["https://openalex.org/I181233156"],"apc_list":{"value":4640,"currency":"USD","value_usd":4640},"apc_paid":null,"fwci":1.2255,"has_fulltext":false,"cited_by_count":12,"citation_normalized_percentile":{"value":0.74235765,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":93,"max":98},"biblio":{"volume":"29","issue":"40","first_page":"e202301153","last_page":"e202301153"},"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":0.9994999766349792,"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":0.9994999766349792,"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/T12653","display_name":"Cyclization and Aryne Chemistry","score":9.999999747378752e-05,"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/T10807","display_name":"Synthesis and characterization of novel inorganic/organometallic compounds","score":9.999999747378752e-05,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/antiaromaticity","display_name":"antiaromaticity","score":0.9399999976158142},{"id":"https://openalex.org/keywords/paratropicity","display_name":"paratropicity","score":0.7260000109672546},{"id":"https://openalex.org/keywords/s-indacene","display_name":"s-indacene","score":0.7080000042915344},{"id":"https://openalex.org/keywords/structural-isomers","display_name":"structural isomers","score":0.6880000233650208},{"id":"https://openalex.org/keywords/mesityl-group","display_name":"mesityl group","score":0.5490000247955322},{"id":"https://openalex.org/keywords/nmr-chemical-shifts","display_name":"NMR chemical shifts","score":0.7860000133514404},{"id":"https://openalex.org/keywords/uv-vis-spectra","display_name":"UV-Vis spectra","score":0.7799999713897705},{"id":"https://openalex.org/keywords/cyclic-voltammetry","display_name":"cyclic voltammetry","score":0.9810000061988831}],"concepts":[{"id":"https://openalex.org/C55213715","wikidata":"https://www.wikidata.org/wiki/Q574842","display_name":"Antiaromaticity","level":4,"score":0.9713720083236694},{"id":"https://openalex.org/C143724316","wikidata":"https://www.wikidata.org/wiki/Q312468","display_name":"Series (stratigraphy)","level":2,"score":0.7908125519752502},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.38618412613868713},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3346136510372162},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.33174145221710205},{"id":"https://openalex.org/C202444582","wikidata":"https://www.wikidata.org/wiki/Q837863","display_name":"Pure mathematics","level":1,"score":0.3234679698944092},{"id":"https://openalex.org/C127313418","wikidata":"https://www.wikidata.org/wiki/Q1069","display_name":"Geology","level":0,"score":0.17417901754379272},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.11812445521354675},{"id":"https://openalex.org/C151730666","wikidata":"https://www.wikidata.org/wiki/Q7205","display_name":"Paleontology","level":1,"score":0.1101703941822052},{"id":"https://openalex.org/C192386470","wikidata":"https://www.wikidata.org/wiki/Q210390","display_name":"Aromaticity","level":3,"score":0.06582909822463989},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.05231645703315735}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1002/chem.202301153","doi":"https://doi.org/10.1002/chem.202301153","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.202301153","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry \u2013 A European Journal","raw_type":"journal-article"},{"id":"pmid:37146211","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/37146211","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":"Chemistry (Weinheim an der Bergstrasse, Germany)","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G4394365630","display_name":null,"funder_award_id":"CHE-1954389","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":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":48,"referenced_works":["https://openalex.org/W625378497","https://openalex.org/W1524660474","https://openalex.org/W1592878305","https://openalex.org/W1890847042","https://openalex.org/W1989727052","https://openalex.org/W2003516675","https://openalex.org/W2009046603","https://openalex.org/W2010047027","https://openalex.org/W2012415341","https://openalex.org/W2020400781","https://openalex.org/W2034076698","https://openalex.org/W2036578811","https://openalex.org/W2050791206","https://openalex.org/W2071588921","https://openalex.org/W2075533627","https://openalex.org/W2114533342","https://openalex.org/W2118946568","https://openalex.org/W2132454074","https://openalex.org/W2132525235","https://openalex.org/W2148502720","https://openalex.org/W2312764173","https://openalex.org/W2323246623","https://openalex.org/W2327166481","https://openalex.org/W2389596035","https://openalex.org/W2557852966","https://openalex.org/W2588478311","https://openalex.org/W2593499778","https://openalex.org/W2599745687","https://openalex.org/W2768135961","https://openalex.org/W2804232296","https://openalex.org/W2914009328","https://openalex.org/W2947576990","https://openalex.org/W2949132418","https://openalex.org/W2949394667","https://openalex.org/W2950316992","https://openalex.org/W3010911919","https://openalex.org/W3092740916","https://openalex.org/W3092757997","https://openalex.org/W3112134513","https://openalex.org/W3166466310","https://openalex.org/W3189308821","https://openalex.org/W3192708436","https://openalex.org/W4205962703","https://openalex.org/W4240320014","https://openalex.org/W4245487146","https://openalex.org/W4250403357","https://openalex.org/W4321505656","https://openalex.org/W6631442365"],"related_works":["https://openalex.org/W3166466310","https://openalex.org/W4285043583","https://openalex.org/W3214811749","https://openalex.org/W4388523258","https://openalex.org/W4408816006","https://openalex.org/W3203368265","https://openalex.org/W4212893069","https://openalex.org/W2898717959","https://openalex.org/W7168084307","https://openalex.org/W4408294318"],"abstract_inverted_index":{"Fusion":[0],"of":[1,14,22,25,65,100,104],"aromatic":[2],"subunits":[3],"to":[4,57,71,112],"stabilize":[5],"an":[6],"antiaromatic":[7,93],"core":[8],"allows":[9],"the":[10,34,43,52,66,72,88,91,101,107,113],"isolation":[11],"and":[12,82,95],"study":[13,21],"otherwise":[15],"unstable":[16],"paratropic":[17],"systems.":[18],"A":[19],"complete":[20],"a":[23,97],"series":[24],"six":[26,67],"naphthothiophene-fused":[27],"s-indacene":[28],"isomers":[29,68],"is":[30,69],"herein":[31],"described.":[32],"Additionally,":[33],"structural":[35],"modifications":[36],"resulted":[37],"in":[38,42,59],"increased":[39],"\u03c0-\u03c0":[40],"overlap":[41],"solid":[44],"state,":[45],"which":[46],"was":[47],"further":[48],"explored":[49],"through":[50],"changing":[51],"sterically":[53],"blocking":[54],"mesityl":[55],"group":[56],"(triisopropylsilyl)ethynyl":[58],"three":[60],"derivatives.":[61],"The":[62],"computed":[63],"antiaromaticity":[64],"compared":[70,111],"observed":[73],"physical":[74],"properties,":[75],"such":[76],"as":[77],"NMR":[78],"chemical":[79],"shift,":[80],"UV-vis,":[81],"CV":[83],"data.":[84],"We":[85],"find":[86],"that":[87],"calculations":[89],"predict":[90],"most":[92],"isomer":[94],"give":[96],"general":[98],"estimation":[99],"relative":[102],"degree":[103],"paratropicity":[105],"for":[106],"remaining":[108],"isomers,":[109],"when":[110],"experimental":[114],"results.":[115]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":4},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":2}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2023-05-07T00:00:00"}