{"title":"含有噻唑、异噻唑、噻二唑和异噻二唑的氮光开关。","authors":"Nusaiba Madappuram Cheruthu , P. K. Hashim , Saugata Sahu , Kiyonori Takahashi , Takayoshi Nakamura , Hideyuki Mitomo , Kuniharu Ijiro , Nobuyuki Tamaoki","doi":"10.1039/d4ob01573h","DOIUrl":null,"url":null,"abstract":"<div><div>We report a novel class of azophotoswitches incorporating various five-membered heteroaryl units such as thiazole, isothiazole, thiadiazole, and isothiadiazole. These azophotoswitches were developed through an initial screening of 24 compounds using DFT calculations to identify those with the wavelength of maximum absorption (<em>λ</em><sub>max</sub>) at a long wavelength. Subsequently, eight selected azophotoswitches were synthesized. Compounds containing both thiazole and isothiazole moieties showed relatively long <em>λ</em><sub>max</sub> compared to the other synthesized compounds. These azophotoswitches exhibited reversible isomerization under visible light irradiation at 430 nm, 450 nm, 470 nm (<em>trans</em> to <em>cis</em>) and 525 nm (<em>cis</em> to <em>trans</em>). Analysis of the X-ray crystal structures of the <em>cis</em> isomer of phenylazo[1,3,4-thiadiazole] exhibited a unique orthogonal geometry.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 1","pages":"Pages 207-212"},"PeriodicalIF":2.9000,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Azophotoswitches containing thiazole, isothiazole, thiadiazole, and isothiadiazole†\",\"authors\":\"Nusaiba Madappuram Cheruthu , P. K. Hashim , Saugata Sahu , Kiyonori Takahashi , Takayoshi Nakamura , Hideyuki Mitomo , Kuniharu Ijiro , Nobuyuki Tamaoki\",\"doi\":\"10.1039/d4ob01573h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We report a novel class of azophotoswitches incorporating various five-membered heteroaryl units such as thiazole, isothiazole, thiadiazole, and isothiadiazole. These azophotoswitches were developed through an initial screening of 24 compounds using DFT calculations to identify those with the wavelength of maximum absorption (<em>λ</em><sub>max</sub>) at a long wavelength. Subsequently, eight selected azophotoswitches were synthesized. Compounds containing both thiazole and isothiazole moieties showed relatively long <em>λ</em><sub>max</sub> compared to the other synthesized compounds. These azophotoswitches exhibited reversible isomerization under visible light irradiation at 430 nm, 450 nm, 470 nm (<em>trans</em> to <em>cis</em>) and 525 nm (<em>cis</em> to <em>trans</em>). Analysis of the X-ray crystal structures of the <em>cis</em> isomer of phenylazo[1,3,4-thiadiazole] exhibited a unique orthogonal geometry.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 1\",\"pages\":\"Pages 207-212\"},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-11-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024009686\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024009686","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Azophotoswitches containing thiazole, isothiazole, thiadiazole, and isothiadiazole†
We report a novel class of azophotoswitches incorporating various five-membered heteroaryl units such as thiazole, isothiazole, thiadiazole, and isothiadiazole. These azophotoswitches were developed through an initial screening of 24 compounds using DFT calculations to identify those with the wavelength of maximum absorption (λmax) at a long wavelength. Subsequently, eight selected azophotoswitches were synthesized. Compounds containing both thiazole and isothiazole moieties showed relatively long λmax compared to the other synthesized compounds. These azophotoswitches exhibited reversible isomerization under visible light irradiation at 430 nm, 450 nm, 470 nm (trans to cis) and 525 nm (cis to trans). Analysis of the X-ray crystal structures of the cis isomer of phenylazo[1,3,4-thiadiazole] exhibited a unique orthogonal geometry.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.