Synthesis and properties of novel extended BODIPYs with rigid skeletons

Synthesis and properties of novel extended BODIPYs with rigid skeletons
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DOI:
10.1016/j.tetlet.2019.01.046
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发表时间:
2019-03-07
影响因子:
1.8
通讯作者:
Oba, Toru
Oba, Toru
中科院分区:
化学4区
文献类型:
--
作者:
Kawamata, Yuki;Ito, Satoshi;Oba, Toru

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以双环吡咯为原料,通过Knoevenagel缩合、Suzuki偶联和O-螯合合成了新型延伸的双环稠合BODIPY。 BODIPY 的最大吸收范围从可见光到近红外区域,并且该化合物在有机溶剂中表现出良好的溶解度。在吡咯单元的α位具有2-萘基的双环BODIPY的溶解度特别高。加热将二苯乙烯基IBODIPY与双环[2.2.2]辛烯转化为苯并BODIPY,在近红外区域有吸收(748.5 nm)和荧光(775.0 nm)。 (C) 2019 Elsevier Ltd. 保留所有权利。
Novel extended BODIPYs fused with bicyclo rings were synthesized from bicyclopyrroles by combining Knoevenagel condensation, Suzuki coupling, and O-chelation. The absorption maxima of the BODIPYs ranged from the visible to near-infrared region and the compounds showed good solubility in organic solvents. The solubility of the bicycloBODIPY with 2-naphthyl groups at the alpha-position of the pyrrole units was particularly high. Heating converted distyryIBODIPY with bicyclo[2.2.2]octene to benzoBODIPY with absorption (748.5 nm) and fluorescence (775.0 nm) in the near-infrared region. (C) 2019 Elsevier Ltd. All rights reserved.