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首页> 外文期刊>Crystal growth & design >Steering Power of Perfluoroalkyl Substituents in Crystal Engineering: Tuning the pi-pi Distance While Maintaining the Lamellar Packing Motif for Aromatics with Various Sizes of pi-Conjugation
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Steering Power of Perfluoroalkyl Substituents in Crystal Engineering: Tuning the pi-pi Distance While Maintaining the Lamellar Packing Motif for Aromatics with Various Sizes of pi-Conjugation

机译：晶体工程中全氟烷基取代基的转向力：调整pi-pi距离，同时保持具有各种pi共轭尺寸的芳香族化合物的层状堆积模体

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摘要

Previously, we reported that introducing perfluoroalkyl substituents onto aromatics promotes the formation of lamellar pi-pi stacked crystalline materials with short interplanar distances. In this report, we developed a new synthetic route that effectively prepares perfluoroalkylated N-containing aromatics by eliminating a side perfluoroalkylation reaction occurring on nonsubstituted C-sp2-H sites of the corresponding bromoaromatics without regioselectivity. This results in a significant improvement of the yield of target perfluoroalkylated aromatics and facilitates the purification and scale-up processes. X-ray single crystal structural analyses show that lamellar pi-pi stacked structures with tunable interplanar distances are achieved with fused N-containing aromatics with varying sizes of a-conjugation. Both crystal structures and theoretical calculations demonstrated that the interplanar distance can be fine-tuned with the size of a-conjugation, with larger a-conjugation favoring shorter interplanar distances while still maintaining a lamellar pi-pi stacked packing motif: Compared to our previous results, we find that simply changing the perfluoroalkyl substituent positions and patterns can change molecular topology to exclusively form lamellar pi-pi stacked packing motifs through prioritization of specific steric effects. Electrochemical results and absorption spectra confirm that the band gap is reduced due to increasing pi-conjugation, and the first reduction potential exhibits a significant positive shift due to both increasing pi-conjugation and perfluoroalkylation.
机译：以前，我们报道过将全氟烷基取代基引入芳族化合物会促进层间pi-pi堆叠的晶面间距短的晶体材料的形成。在本报告中，我们开发了一条新的合成路线，该路线可通过消除相应溴代芳烃的未取代C-sp2-H位上发生的副全氟烷基化反应而无区域选择性的方式，有效地制备全氟烷基化的含N芳族化合物。这导致目标全氟烷基化芳族化合物的收率显着提高，并有助于纯化和放大工艺。 X射线单晶结构分析表明，具有可变a共轭尺寸的稠合含N芳族化合物可实现晶面间距可调的层状pi-pi堆叠结构。晶体结构和理论计算均表明，可以通过a共轭的大小微调平面间距，较大的a共轭有利于缩短平面间距，同时仍保持层状pi-pi堆积堆积图案：与我们之前的结果相比，我们发现简单地改变全氟烷基取代基的位置和样式可以改变分子的拓扑结构，从而通过优先考虑特定的空间效应来专门形成层状pi-pi堆积的包装图案。电化学结果和吸收光谱证实，由于增加的π共轭，带隙减小，并且由于增加的π共轭和全氟烷基化，第一还原电位显示出显着的正位移。

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