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On the Structure and Chiral Aggregation of Liquid Crystalline Star-Shaped Triazines H-Bonded to Benzoic Acids.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-06-30 , DOI: 10.1002/chem.202001271 Beatriz Feringán 1 , Jesús Cerdá 2 , Beatriz Diosdado 1 , Juan Aragó 2 , Enrique Ortí 2 , Raquel Giménez 1 , Teresa Sierra 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-06-30 , DOI: 10.1002/chem.202001271 Beatriz Feringán 1 , Jesús Cerdá 2 , Beatriz Diosdado 1 , Juan Aragó 2 , Enrique Ortí 2 , Raquel Giménez 1 , Teresa Sierra 1
Affiliation
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The ability of a star‐shaped tris(triazolyl)triazine derivative to hierarchically build supramolecular chiral columnar organizations through the formation of H‐bonded complexes with benzoic acids was studied from a theoretical and experimental point of view. The combined study has been done at three different levels including the study of the structure of the triazine core, the association with benzoic acids in stoichiometry 1:3, and the assembly of 1:3 complexes in helical aggregates. Although the star‐shaped triazine core crystallizes in a non‐C3 conformation, the C3‐symmetric conformation is theoretically predicted to be more stable and gives rise to a favorable C3 supramolecular 1:3 complex upon the interaction with three benzoic acids in their voids. In addition, calculations at different levels (DFT, PM7, and MM3) for the 1:3 host‐guest complex predict the formation of large stable columnar helical aggregates stabilized by the compact packing of the interstitial acids by π–π and CH⋅⋅⋅π interactions. The acids restrict the movement of the the star‐shaped triazine cores along the stacking axis causing a template effect in the self‐assembly of the complex. Theoretical predictions correlate with experimental results, since the interaction with achiral or chiral 3,4,5‐(4‐alkoxybenzyloxy)benzoic acids gives rise to supramolecular complexes that organize in bulk hexagonal columnar mesophases stable at room temperature with intracolumnar order. The existence of supramolecular chirality in the mesophase was determined for complexes formed by acids derived from (S)‐2‐octanol. Chiral aggregation was also evidenced for complexes formed in dodecane.
中文翻译：
氢键合于苯甲酸的液晶星状三嗪的结构和手性聚集
从理论和实验的角度研究了星形三（三唑基）三嗪衍生物通过与苯甲酸形成H键合的配合物来分层构建超分子手性柱状组织的能力。已在三个不同级别进行了组合研究，包括研究三嗪核心的结构，化学计量比为1：3的苯甲酸的结合以及螺旋聚集体的1：3配合物的组装。尽管星形三嗪核结晶为非C 3构型，但理论上预测C 3对称构型更稳定，并产生有利的C 3超分子1：3配合物，在其空隙中与三种苯甲酸相互作用。此外，对于1：3主客体复合物，在不同水平（DFT，PM7和MM3）上进行的计算可预测形成大的稳定柱状螺旋聚集体，该聚集体由填隙酸通过π-π和CH⋅⋅的紧密堆积而稳定⋅π相互作用。酸限制了星形三嗪核沿着堆积轴的移动，从而在复合物的自组装中产生模板效应。理论预测与实验结果相关，因为与非手性或手性3,4,5-（4-烷氧基苄氧基）苯甲酸的相互作用产生了超分子复合物，该复合物在室温下稳定地以柱内有序排列的本体六方柱状中间相组成。S）-2-辛醇 在十二烷中形成的复合物也证明了手性聚集。
更新日期：2020-06-30
中文翻译：
氢键合于苯甲酸的液晶星状三嗪的结构和手性聚集
从理论和实验的角度研究了星形三（三唑基）三嗪衍生物通过与苯甲酸形成H键合的配合物来分层构建超分子手性柱状组织的能力。已在三个不同级别进行了组合研究，包括研究三嗪核心的结构，化学计量比为1：3的苯甲酸的结合以及螺旋聚集体的1：3配合物的组装。尽管星形三嗪核结晶为非C 3构型，但理论上预测C 3对称构型更稳定，并产生有利的C 3超分子1：3配合物，在其空隙中与三种苯甲酸相互作用。此外，对于1：3主客体复合物，在不同水平（DFT，PM7和MM3）上进行的计算可预测形成大的稳定柱状螺旋聚集体，该聚集体由填隙酸通过π-π和CH⋅⋅的紧密堆积而稳定⋅π相互作用。酸限制了星形三嗪核沿着堆积轴的移动，从而在复合物的自组装中产生模板效应。理论预测与实验结果相关，因为与非手性或手性3,4,5-（4-烷氧基苄氧基）苯甲酸的相互作用产生了超分子复合物，该复合物在室温下稳定地以柱内有序排列的本体六方柱状中间相组成。S）-2-辛醇 在十二烷中形成的复合物也证明了手性聚集。
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