Controlled interconversion of macrocyclic atropisomers via defined intermediates

Xin Sun, Jin-Ku Bai, Yu-Dong Yang, Ke-Lin Zhu, Jia-Qi Liang, Xin-Yue Wang, Jun-Feng Xiang, Xiang Hao, Tong-Ling Liang, Ai-Jiao Guan, Ning-Ning Wu and Han-Yuan Gong ()
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Xin Sun: Beijing Normal University
Jin-Ku Bai: Beijing Normal University
Yu-Dong Yang: Beijing Normal University
Ke-Lin Zhu: Beijing Normal University
Jia-Qi Liang: Beijing Normal University
Xin-Yue Wang: Beijing Normal University
Jun-Feng Xiang: Chinese Academy of Sciences
Xiang Hao: Chinese Academy of Sciences
Tong-Ling Liang: Chinese Academy of Sciences
Ai-Jiao Guan: Chinese Academy of Sciences
Ning-Ning Wu: Chinese Academy of Sciences
Han-Yuan Gong: Beijing Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Macrocyclic conformations play a crucial role in regulating their properties. Our understanding of the determinants to control macrocyclic conformation interconversion is still in its infancy. Here we present a macrocycle, octamethyl cyclo[4](1,3-(4,6)-dimethylbenzene)[4]((4,6-benzene)(1,3-dicarboxylate) (OC-4), that can exist at 298 K as two stable atropisomers with C2v and C4v symmetry denoted as C2v-OC-4 and C4v-OC-4, respectively. Heating induces the efficient stepwise conversion of C2v- to C4v-OC-4 via a Cs-symmetric intermediate (Cs-OC-4). It differs from the typical transition state-mediated processes of simple C–C single bond rotations. Hydrolysis and further esterification with a countercation dependence promote the generation of C2v- and Cs-OC-4 from C4v-OC-4. In contrast to C2v-OC-4, C4v-OC-4 can bind linear guests to form pseudo-rotaxans, or bind C60 or C70 efficiently. The present study highlights the differences in recognition behavior that can result from conformational interconversion, as well as providing insights into the basic parameters that govern coupled molecular rotations.

Date: 2024
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DOI: 10.1038/s41467-024-50739-6

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