{"title":"五环 N-杂环羰基二噻吩的高效合成及其光致变色特性","authors":"","doi":"10.1016/j.tetlet.2024.155315","DOIUrl":null,"url":null,"abstract":"<div><div>Given that the photochromic functional materials possess outstanding phototropic color-change properties, the attention being paid to this field is progressively intensifying. The development of <em>N</em>-heterocyclic carbonyl photoswitching materials, harnessing dithienylethene site for photochromism, typically involves a complex multi-step synthesis process, which substrate diversification and the complexity of the preparation process are confronted with various challenges. Herein, we present a straightforward synthetic methodology for the preparation of photochromic 4,5-bis(2,5-dimethylthiophen-3-yl)-1,3-diphenyl-1,3-dihydro-2<em>H</em>-imidazol-2-one (<strong>1o</strong>) via reprogramming the synthesis pathway of dithienylethene-containing imidazolone using 1,3-diphenylurea. The current method demonstrates efficient reaction between α-hydroxy ketone and 1,3-diphenylurea in high yield, thereby enabling direct and straightforward one-step cyclization. The grown crystal sample of the targeted <strong>1o</strong> has undergone single crystal X-ray diffraction analysis to elucidate its structural information. The ring-open (<em>o</em>-isomer) and ring-closed (<em>c</em>-isomer) forms showing remarkable fatigue resistance and high contrast visual color changes, can be effortlessly interconverted through the alternating irradiation of UV/vis light. To illustrate the electronic structure of the isomers, thorough analyses of the frontier molecular orbital based on TD-DFT calculations were conducted.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Highly efficient synthesis and photochromic properties of a pentacyclic N-heterocyclic carbonyl-based dithienylethene\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155315\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Given that the photochromic functional materials possess outstanding phototropic color-change properties, the attention being paid to this field is progressively intensifying. The development of <em>N</em>-heterocyclic carbonyl photoswitching materials, harnessing dithienylethene site for photochromism, typically involves a complex multi-step synthesis process, which substrate diversification and the complexity of the preparation process are confronted with various challenges. Herein, we present a straightforward synthetic methodology for the preparation of photochromic 4,5-bis(2,5-dimethylthiophen-3-yl)-1,3-diphenyl-1,3-dihydro-2<em>H</em>-imidazol-2-one (<strong>1o</strong>) via reprogramming the synthesis pathway of dithienylethene-containing imidazolone using 1,3-diphenylurea. The current method demonstrates efficient reaction between α-hydroxy ketone and 1,3-diphenylurea in high yield, thereby enabling direct and straightforward one-step cyclization. The grown crystal sample of the targeted <strong>1o</strong> has undergone single crystal X-ray diffraction analysis to elucidate its structural information. The ring-open (<em>o</em>-isomer) and ring-closed (<em>c</em>-isomer) forms showing remarkable fatigue resistance and high contrast visual color changes, can be effortlessly interconverted through the alternating irradiation of UV/vis light. To illustrate the electronic structure of the isomers, thorough analyses of the frontier molecular orbital based on TD-DFT calculations were conducted.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-09-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004106\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004106","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Highly efficient synthesis and photochromic properties of a pentacyclic N-heterocyclic carbonyl-based dithienylethene
Given that the photochromic functional materials possess outstanding phototropic color-change properties, the attention being paid to this field is progressively intensifying. The development of N-heterocyclic carbonyl photoswitching materials, harnessing dithienylethene site for photochromism, typically involves a complex multi-step synthesis process, which substrate diversification and the complexity of the preparation process are confronted with various challenges. Herein, we present a straightforward synthetic methodology for the preparation of photochromic 4,5-bis(2,5-dimethylthiophen-3-yl)-1,3-diphenyl-1,3-dihydro-2H-imidazol-2-one (1o) via reprogramming the synthesis pathway of dithienylethene-containing imidazolone using 1,3-diphenylurea. The current method demonstrates efficient reaction between α-hydroxy ketone and 1,3-diphenylurea in high yield, thereby enabling direct and straightforward one-step cyclization. The grown crystal sample of the targeted 1o has undergone single crystal X-ray diffraction analysis to elucidate its structural information. The ring-open (o-isomer) and ring-closed (c-isomer) forms showing remarkable fatigue resistance and high contrast visual color changes, can be effortlessly interconverted through the alternating irradiation of UV/vis light. To illustrate the electronic structure of the isomers, thorough analyses of the frontier molecular orbital based on TD-DFT calculations were conducted.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.