{"title":"Azobenzene protonation as a tool for temperature sensing.","authors":"Antti Siiskonen, Sami Vesamäki, Arri Priimagi","doi":"10.3762/bjoc.21.115","DOIUrl":null,"url":null,"abstract":"<p><p>Azobenzenes can be protonated at one of the azo nitrogen atoms, leading to significant changes in their absorption and photochemical properties. While azobenzene protonation has been recently used as a tool in photoswitching studies, the factors influencing protonation itself have received little attention. Here, we report a strong temperature dependence of azobenzene protonation in 1,2-dichloroethane and highlight its potential for temperature sensing applications. Density functional theory calculations were performed to support our findings and to investigate the mechanisms of azobenzene-acid interactions, aiming to guide the design of azobenzene-based temperature sensors in future research.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1528-1534"},"PeriodicalIF":2.1000,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12320741/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.21.115","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Azobenzenes can be protonated at one of the azo nitrogen atoms, leading to significant changes in their absorption and photochemical properties. While azobenzene protonation has been recently used as a tool in photoswitching studies, the factors influencing protonation itself have received little attention. Here, we report a strong temperature dependence of azobenzene protonation in 1,2-dichloroethane and highlight its potential for temperature sensing applications. Density functional theory calculations were performed to support our findings and to investigate the mechanisms of azobenzene-acid interactions, aiming to guide the design of azobenzene-based temperature sensors in future research.
期刊介绍:
The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.