{"title":"溶液处理光电器件中5,5 ' -烷基取代靛蓝","authors":"Motonori Watanabe , Naoki Uemura , Shintaro Ida , Hidehisa Hagiwara , Kenta Goto , Tatsumi Ishihara","doi":"10.1016/j.tet.2016.05.069","DOIUrl":null,"url":null,"abstract":"<div><p><span>A series of alkylated indigos were synthesized. Alkylated indigos were characterized by NMR<span><span><span>, mass spectrometry, absorption spectra, cyclic voltammetry, and density functional theory (DFT) calculations. </span>Propyl<span> and butyl group substituted indigo was most soluble in chloroform and 1,2-dicrolobenzene, and these solubility were 65–89 times increased as compared to the parent indigo. DFT calculations suggested that the presence of the alkyl chains at the 5.5′-position increases the energy of the highest occupied </span></span>molecular orbital<span>, while reducing the energy of the lowest unoccupied molecular orbital. This theoretical finding was in good agreement with the experimental results. Crystal structures obtained by X-ray diffraction showed one-dimensional pi–pi stacking. Alkylated molecules were converted to leuco structure, and these structures were then converted to the corresponding indigos in the film state. After deposition of the films on TiO</span></span></span><sub>2</sub><span>/FTO substrate, oxidative photocurrents were observed.</span></p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2016-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tet.2016.05.069","citationCount":"0","resultStr":"{\"title\":\"5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices\",\"authors\":\"Motonori Watanabe , Naoki Uemura , Shintaro Ida , Hidehisa Hagiwara , Kenta Goto , Tatsumi Ishihara\",\"doi\":\"10.1016/j.tet.2016.05.069\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p><span>A series of alkylated indigos were synthesized. Alkylated indigos were characterized by NMR<span><span><span>, mass spectrometry, absorption spectra, cyclic voltammetry, and density functional theory (DFT) calculations. </span>Propyl<span> and butyl group substituted indigo was most soluble in chloroform and 1,2-dicrolobenzene, and these solubility were 65–89 times increased as compared to the parent indigo. DFT calculations suggested that the presence of the alkyl chains at the 5.5′-position increases the energy of the highest occupied </span></span>molecular orbital<span>, while reducing the energy of the lowest unoccupied molecular orbital. This theoretical finding was in good agreement with the experimental results. Crystal structures obtained by X-ray diffraction showed one-dimensional pi–pi stacking. Alkylated molecules were converted to leuco structure, and these structures were then converted to the corresponding indigos in the film state. After deposition of the films on TiO</span></span></span><sub>2</sub><span>/FTO substrate, oxidative photocurrents were observed.</span></p></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2016-07-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.tet.2016.05.069\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402016304860\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402016304860","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices
A series of alkylated indigos were synthesized. Alkylated indigos were characterized by NMR, mass spectrometry, absorption spectra, cyclic voltammetry, and density functional theory (DFT) calculations. Propyl and butyl group substituted indigo was most soluble in chloroform and 1,2-dicrolobenzene, and these solubility were 65–89 times increased as compared to the parent indigo. DFT calculations suggested that the presence of the alkyl chains at the 5.5′-position increases the energy of the highest occupied molecular orbital, while reducing the energy of the lowest unoccupied molecular orbital. This theoretical finding was in good agreement with the experimental results. Crystal structures obtained by X-ray diffraction showed one-dimensional pi–pi stacking. Alkylated molecules were converted to leuco structure, and these structures were then converted to the corresponding indigos in the film state. After deposition of the films on TiO2/FTO substrate, oxidative photocurrents were observed.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.