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Chiral‐at‐Metal BODIPY‐Based Iridium(III) Complexes: Synthesis and Luminescence Properties
European Journal of Inorganic Chemistry ( IF 2.2 ) Pub Date : 2020-08-25 , DOI: 10.1002/ejic.202000745 Marta G. Avello 1, 2 , María C. de la Torre 1, 2 , Andrés Guerrero‐Martínez 3 , Miguel A. Sierra 2, 4 , Heinz Gornitzka 5 , Catherine Hemmert 5
European Journal of Inorganic Chemistry ( IF 2.2 ) Pub Date : 2020-08-25 , DOI: 10.1002/ejic.202000745 Marta G. Avello 1, 2 , María C. de la Torre 1, 2 , Andrés Guerrero‐Martínez 3 , Miguel A. Sierra 2, 4 , Heinz Gornitzka 5 , Catherine Hemmert 5
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The synthesis of enantiomerically pure Ir(III) complexes with one or two BODIPY moieties has been achieved through the enantioselective C–H insertion from homochiral triazolium salts, containing a sulfoxide functionality in their structures. These homochiral salts were prepared by the sequential Cu‐catalyzed alkyne‐azide cycloaddition (CuAAC) of an azide and one alkynyl sulfoxide, followed by a Suzuki coupling in the preformed triazole with a BODIPY containing aryl boronic acid, followed by methylation of the N3‐triazole nitrogen. The configuration at the metal in these chiral complexes was established by using a combination of CD and X‐ray diffraction techniques. The optical properties of these complexes were thoroughly studied using spectroscopic (absorption and fluorescence) and computational (TD‐DFT and DFT) methods. The fluorescence of complexes with the BODIPY attached to the sulfoxide moiety (including the two BODIPYs‐based complex) was quenched upon introduction of the Ir(III) fragment, most likely due to an a‐PET mechanism. On the contrary, the fluorescence of Ir(III) complexes with the BODIPY attached to the triazolium ring remains unquenched.
中文翻译：
基于手性金属BODIPY的铱（III）配合物：合成和发光性质
对映体纯的Ir（III）配合物具有一个或两个BODIPY部分的合成是通过从手性三唑鎓盐中对映选择性C–H插入而实现的，其结构中含有亚砜官能团。这些均手性盐的制备方法是依次进行叠氮化物和一种炔基亚砜的Cu催化炔叠氮化物环加成（CuAAC），然后在预先形成的三唑中与含有芳基硼酸的BODIPY进行Suzuki偶联，然后对N3-三唑氮。这些手性络合物中金属的构型是通过结合CD和X射线衍射技术确定的。使用光谱（吸收和荧光）和计算（TD-DFT和DFT）方法对这些配合物的光学性质进行了深入研究。引入Ir（III）片段后，具有连接到亚砜部分的BODIPY的复合物（包括两个基于BODIPYs的复合物）的荧光被猝灭，这很可能是由于a- PET机制引起的。相反，与三唑鎓环连接的BODIPY的Ir（III）配合物的荧光仍未猝灭。
更新日期：2020-08-25
中文翻译：
基于手性金属BODIPY的铱（III）配合物：合成和发光性质
对映体纯的Ir（III）配合物具有一个或两个BODIPY部分的合成是通过从手性三唑鎓盐中对映选择性C–H插入而实现的，其结构中含有亚砜官能团。这些均手性盐的制备方法是依次进行叠氮化物和一种炔基亚砜的Cu催化炔叠氮化物环加成（CuAAC），然后在预先形成的三唑中与含有芳基硼酸的BODIPY进行Suzuki偶联，然后对N3-三唑氮。这些手性络合物中金属的构型是通过结合CD和X射线衍射技术确定的。使用光谱（吸收和荧光）和计算（TD-DFT和DFT）方法对这些配合物的光学性质进行了深入研究。引入Ir（III）片段后，具有连接到亚砜部分的BODIPY的复合物（包括两个基于BODIPYs的复合物）的荧光被猝灭，这很可能是由于a- PET机制引起的。相反，与三唑鎓环连接的BODIPY的Ir（III）配合物的荧光仍未猝灭。
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