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Coal‐Tar Dye‐based Coordination Cages and Helicates
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-11-27 , DOI: 10.1002/anie.202015246 Irene Regeni 1 , Bin Chen 1, 2 , Marina Frank 1 , Ananya Baksi 1 , Julian J Holstein 1 , Guido H Clever 1
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-11-27 , DOI: 10.1002/anie.202015246 Irene Regeni 1 , Bin Chen 1, 2 , Marina Frank 1 , Ananya Baksi 1 , Julian J Holstein 1 , Guido H Clever 1
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A strategy to implement four members of the classic coal‐tar dye family, Michler's ketone, methylene blue, rhodamine B, and crystal violet, into [Pd2L4] self‐assemblies is introduced. Chromophores were incorporated into bis‐monodentate ligands using piperazine linkers that allow to retain the auxochromic dialkyl amine functionalities required for intense colors deep in the visible spectrum. Upon palladium coordination, ligands with pyridine donors form lantern‐shaped dinuclear cages while quinoline donors lead to strongly twisted [Pd2L4] helicates in solution. In one case, single crystal X‐ray diffraction revealed rearrangement to a [Pd3L6] ring structure in the solid state. For nine examined derivatives, showing colors from yellow to deep violet, CD spectroscopy discloses different degrees of chiral induction by an enantiomerically pure guest. Ion mobility mass spectrometry allows to distinguish two binding modes. Self‐assemblies based on this new ligand class promise application in chiroptical recognition, photo‐redox catalysis and optical materials.
中文翻译：
基于煤焦油染料的配位笼和螺旋
引入了将经典煤焦油染料家族的四种成员（米蚩酮、亚甲基蓝、罗丹明 B 和结晶紫）应用到 [Pd 2 L 4 ] 自组装中的策略。使用哌嗪连接体将发色团整合到双单齿配体中，该连接体允许保留可见光谱深处的强烈颜色所需的助色二烷基胺官能团。钯配位后，配体与吡啶供体形成灯笼形双核笼，而喹啉供体在溶液中形成强烈扭曲的[Pd 2 L 4 ]螺旋。在一种情况下，单晶X射线衍射揭示了固态下[Pd 3 L 6 ]环结构的重排。对于九种检查的衍生物，显示从黄色到深紫色的颜色，CD光谱揭示了对映体纯客体不同程度的手性诱导。离子淌度质谱分析可以区分两种结合模式。基于这种新配体类的自组装有望在手性光学识别、光氧化还原催化和光学材料中得到应用。
更新日期：2020-11-27
中文翻译：
基于煤焦油染料的配位笼和螺旋
引入了将经典煤焦油染料家族的四种成员（米蚩酮、亚甲基蓝、罗丹明 B 和结晶紫）应用到 [Pd 2 L 4 ] 自组装中的策略。使用哌嗪连接体将发色团整合到双单齿配体中，该连接体允许保留可见光谱深处的强烈颜色所需的助色二烷基胺官能团。钯配位后，配体与吡啶供体形成灯笼形双核笼，而喹啉供体在溶液中形成强烈扭曲的[Pd 2 L 4 ]螺旋。在一种情况下，单晶X射线衍射揭示了固态下[Pd 3 L 6 ]环结构的重排。对于九种检查的衍生物，显示从黄色到深紫色的颜色，CD光谱揭示了对映体纯客体不同程度的手性诱导。离子淌度质谱分析可以区分两种结合模式。基于这种新配体类的自组装有望在手性光学识别、光氧化还原催化和光学材料中得到应用。
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