噻吩[3,2-b:4,5-b′]双苯并呋喃类化合物的合成及光物理性质研究  

Synthesis and photophysical properties of thieno[3,2-b:4,5-b′]bis[1]benzofuran compounds

作　　者：杨云 岳二林 高源 姬宝宝 张玉琦[1] 王记江[1] YANG Yun;YUE Erlin;GAO Yuan;JI Baobao;ZHANG Yuqi;WANG Jijiang(Yan’an Key Laboratory of New Energy Materials,Shaanxi Key Laboratory of Chemical Reaction Engineering,School of Chemistry and Chemical Engineering,Yan’an University,Yan’an 716000,China)

机构地区：[1]延安大学化学与化工学院,延安市新能源新功能材料重点实验室,陕西省化学反应工程重点实验室,陕西延安716000

出　　处：《延安大学学报（自然科学版）》2024年第2期1-7,共7页Journal of Yan'an University：Natural Science Edition

基　　金：陕西省科技厅自然科学基金项目(2021JQ-614);延安市高层次人才专项项目(2019-33);延安大学大学生创新训练项目(D2021030)。

摘　　要：噻吩[3,2-b:4,5-b′]双苯并呋喃稠杂环化合物是一类重要的用于有机光电材料的并五苯的衍生物,该类稠杂环化合物的合成具有十分重要的意义。以廉价的2-碘苯甲醚、4-叔丁基-2-碘苯甲醚或2,4-二叔丁基-2-碘苯甲醚为原料,通过经典的Sonogashira偶联反应、脱保护基反应、Glaser-Hay偶联反应、碘亲电环化反应和噻吩合成反应五步反应成功合成了一类结构新颖的稠合杂环类化合物噻吩[3,2-b:4,5-b′]双苯并呋喃。关键的中间体双苯并呋喃二碘化合物(6a)和噻吩[3,2-b:4,5-b′]双苯并呋喃化合物(1a)均由单晶衍射分析确认了结构。该反应路线原料成本低,反应操作简单,总收率较高(1a:54%;1b:40%;1c:47%)。该合成策略为获得这类稠杂环化合物提供了一种有效的合成方法,所制备的化合物具有优异的光物理性质,有望用于光电材料领域。Thieno[3,2-b:4,5-b′]bis[1]benzofuran heterocyclic compounds as an important class of heterocyclic pentacene derivatives have widely used in organic photoelectric materials,and the synthesis of these fused heteracenes is of great significance.The thieno[3,2-b:4,5-b′]bis[1]benzofuran compounds were synthesized via 5-step reactions including the classical Sonogashira coupling,Glaser-Hay coupling,iodine electrophilic cycliza⁃tion and thiophene synthesis reaction with cheap o-iodoanisole,2-tert-butyl-o-iodoanisole or 2,4-tert-butyl-oiodoanisole as the starting materials.The structures of the key intermediates,dibenzofuran diiodide(6a)and thieno[3,2-b:4,5-b′]bis[1]benzofuran compound(1a)were confirmed by single-crystal X-ray diffraction analysis.This reaction route has low raw material cost,simple reaction operation and high total yield(1a:54%;1b:40%;1c;47%).This synthetic strategy provides an efficient synthesis method for the synthesis of such fused heterocyclic compounds.The prepared target compounds have excellent photophysical properties and thus can be expected to be used in photoelectric materials.

关 键 词：噻吩[3 2-b:4 5-b′]双苯并呋喃 SONOGASHIRA偶联反应 Glaser-Hay偶联反应 碘亲电环化反应 噻吩合成反应 光物理性质 

分 类 号：O626.2[理学—有机化学]