Efrain Vidal,Lev N Zakharov,Carlos J Gómez-García,Michael M Haley
{"title":"Probing the Influence of Alkyne Substitution on the Electronic and Magnetic Properties of Diindeno[1,2-b;1',2'-i]anthracenes.","authors":"Efrain Vidal,Lev N Zakharov,Carlos J Gómez-García,Michael M Haley","doi":"10.1021/acs.joc.4c01500","DOIUrl":null,"url":null,"abstract":"To further the ability to manipulate the properties of open-shell molecules, logical and incremental modifications to molecular structure are key steps that provide fine-tuning of established diradicaloid scaffolds. We report the synthesis of an electronically \"pure\" diradicaloid based on a 2,6-anthroquinoidal core where the once necessary ethynyl \"wings\" are removed. Through the simplification of the overall electronic structure, the singlet-triplet energy gap increases by 0.3-0.4 kcal mol-1 in the reported diradicaloids while avoiding significant disruption to their optoelectronic properties.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01500","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
To further the ability to manipulate the properties of open-shell molecules, logical and incremental modifications to molecular structure are key steps that provide fine-tuning of established diradicaloid scaffolds. We report the synthesis of an electronically "pure" diradicaloid based on a 2,6-anthroquinoidal core where the once necessary ethynyl "wings" are removed. Through the simplification of the overall electronic structure, the singlet-triplet energy gap increases by 0.3-0.4 kcal mol-1 in the reported diradicaloids while avoiding significant disruption to their optoelectronic properties.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.