Rational design of functionalized near-infrared absorbing phthalocyanines by three-component coupling strategy
Rational design of functionalized near-infrared absorbing phthalocyanines by three-component coupling strategy
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三组分偶联策略合理设计功能化近红外吸收酞菁
DOI：
10.1142/s1088424622300063
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发表时间：
2023
影响因子：
1.5
通讯作者：
Furuyama Taniyuki
中科院分区：
文献类型：
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作者：
Iwamoto Takayuki;Maeda Hajime;Segi Masahito;Furuyama Taniyuki
近红外(NIR)染料广泛应用于有机太阳能电池、光动力治疗增敏剂等领域。一类染料的例子，八芳硫基取代的酞菁(PC)，可以有效地吸收800 nm以上的近红外光。Pc周围硫的取代有效地引入了额外的功能，而不会对光学性质产生显著的影响。然而，含有各种官能化芳硫基的邻苯二甲腈前体的合成一直受到限制。在这里，我们提供了三组分型偶联反应来合成具有不同官能化硫基-芳基的邻苯二甲腈。有机金属试剂是由芳基卤化物、元素硫化物和3，6-bis(trifluoromethanesulfonyloxy)phthalonitrile一锅法合成功能化邻苯二甲腈。采用常用方法制备相应的聚碳酸酯。该反应可扩展到其他16族元素、化学选择性有机镁和有机锌试剂。此外，还揭示了取代效应下PC的近红外吸收和荧光性质，并对其进行了合理化。
Near-infrared (NIR) dyes are used in various applications such as organic solar cells and photodynamic therapy sensitizers. One example of a class of dyes, octa-arylthio-substituted phthalocyanines (Pcs), can effectively absorb NIR light above 800 nm. The substitution of the Pc’s peripheral sulfur effectively introduces extra functions without significant perturbation of the optical properties. However, the synthesis of phthalonitrile precursors containing various functionalized arylthio groups has been limited. Herein, we provide the three-component-type coupling reactions for synthesizing phthalonitriles with various functionalized chalcogen-aryl groups. Organometallic reagents were prepared from aryl halides, elemental chalcogen, and 3,6-bis(trifluoromethanesulfonyloxy)phthalonitrile can lead to functionalized phthalonitriles in a one-pot procedure. Commonly used methods were utilized to prepare the corresponding Pcs. This reaction can be extended to other group-16 elements, chemoselective organomagnesium, and organozincate reagents. The NIR absorption and fluorescence properties of Pcs were also revealed and rationalized under substitution effects.