Development of non-symmetric thiophene-fused BODIPYs
Development of non-symmetric thiophene-fused BODIPYs
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DOI：
10.1016/j.tet.2012.09.011
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发表时间：
2012-11-25
期刊：
影响因子：
2.1
通讯作者：
Zhao, Weili
中科院分区：
文献类型：
--
作者：
Jiang, Xin-Dong;Zhang, Houjun;Zhao, Weili
合成了一系列含噻吩并[3，2-B]吡咯结构的非对称BODIPY，产率为21-63%.吸收和发射最大值覆盖从可见绿色到红色区域（λ（abs）=532-647 nm：λ（em）=547-664 nm; Phi（f）=0.19-0.45）。X射线分析表明，S-C键长比噻吩并吡咯和噻吩并螺烯短0.03-0.05埃。晶体堆积模式表明存在较强的π-π相互作用、分子间C-H中心点F相互作用和较弱的S中心点π相互作用。通过结构修饰实现了可调谐发射。用m-CPBA氧化BODIPY（λ（em）=547 nm）产生噻吩-1，1-二氧化物衍生的BODIPY（λ（em）=528 nm）。BODIPY与N，N-二甲基氨基苯甲醛的Knoevenagel型缩合导致具有延长的共轭的BODIPY（λ（em）=693 nm）。(C)2012爱思唯尔有限公司保留所有权利。
A series of non-symmetric BODIPYs containing thieno[3,2-b]pyrrole moiety were synthesized in 21-63% yields. The absorption and emission maxima covered from the visible green to red region (lambda(abs)=532-647 nm: lambda(em)=547-664 nm; Phi(f)=0.19-0.45). X-ray analysis indicated that the S-C bond lengths were shorter than those of thienopyrrole and thienohelicene by 0.03-0.05 angstrom. The crystal packing pattern suggested that strong pi-pi interaction, intermolecular C-H center dot center dot center dot F interaction, and weak S center dot center dot center dot pi interaction existed. The tunable emission was achieved by structure modifications. Oxidation of BODIPY (lambda(em)=547 nm) with m-CPBA generated thiophene-1,1-dioxide derived BODIPY (lambda(em)=528 nm). Knoevenagel-type condensation of BODIPY with N,N-dimethylaminobenzaldehyde led to BODIPY (lambda(em)=693 nm) with extended conjugation. (C) 2012 Elsevier Ltd. All rights reserved.