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通过炔二醇衍生物的级联环化反应便捷合成取代噻吩并[3,2-]噻吩和硒吩并[3,2-]硒吩

Expedient Synthesis of Substituted Thieno[3,2-]thiophenes and Selenopheno[3,2-]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives.

作者信息

Feng Yingqi, Zhang Xuelin, He Ziqing, Zhao Miaoshan, Chen Lu, Li Yibiao, Luo Xiai

机构信息

Jiangmen Key Laboratory of Synthetic Chemistry and Cleaner Production, School of Environmental & Chemical Engineering, Wuyi University, Jiangmen 529020, China.

Hunan Province Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China.

出版信息

Molecules. 2024 Nov 21;29(23):5507. doi: 10.3390/molecules29235507.

DOI:10.3390/molecules29235507
PMID:39683667
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11643606/
Abstract

Thieno[3,2-]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-]thiophene and selenopheno[3,2-]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I/NaSO or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials.

摘要

噻吩并[3,2 - ]噻吩被用作光电子材料、多孔储氢主体、有机太阳能电池和聚合物半导体中的关键成分。本文提出了一种分步高效的合成方案，通过炔二醇与碘/亚硫酸钠或硒的双硫/双硒环化反应，以中等至良好的产率获得多取代的噻吩并[3,2 - ]噻吩和硒吩并[3,2 - ]硒吩。使用该策略，可获得用于功能材料主链修饰的取代模式。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/add8f7271dd9/molecules-29-05507-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/badebc42c648/molecules-29-05507-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/04a58878e58c/molecules-29-05507-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/68bbbe917a73/molecules-29-05507-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/7be10fc4e053/molecules-29-05507-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/f042b6be7f3b/molecules-29-05507-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/add8f7271dd9/molecules-29-05507-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/badebc42c648/molecules-29-05507-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/04a58878e58c/molecules-29-05507-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/68bbbe917a73/molecules-29-05507-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/7be10fc4e053/molecules-29-05507-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/f042b6be7f3b/molecules-29-05507-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1de/11643606/add8f7271dd9/molecules-29-05507-sch006.jpg

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本文引用的文献

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A Domino Protocol toward High-performance Unsymmetrical Dibenzo[d,d']thieno[2,3-b;4,5-b']dithiophenes Semiconductors.一种用于高性能不对称二苯并[d,d']噻吩并[2,3-b;4,5-b']二噻吩半导体的多米诺协议。
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