Stereoselective Chiral Molecular Carbon Imides Featuring 12-Fold [5]helicenes Around Four Cores

Guogang Liu; Yujian Liu; Chengxi Zhao; Yan Li; Zhaohui Wang; He Tian

doi:10.1002/anie.202214769

Stereoselective Chiral Molecular Carbon Imides Featuring 12-Fold [5]helicenes Around Four Cores

Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202214769. doi: 10.1002/anie.202214769. Epub 2022 Dec 7.

Authors

Guogang Liu¹, Yujian Liu², Chengxi Zhao¹, Yan Li³, Zhaohui Wang², He Tian¹

Affiliations

¹ Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China.
² Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, China.
³ School of Chemistry, Beihang University, Beijing, 100191, China.

PMID: 36357324
DOI: 10.1002/anie.202214769

Abstract

Despite the great progress in research on molecular carbons containing multiple helicenes around one core, realizing the stereoselectivity of carbons containing multiple helicenes around more cores is still a great challenge. Herein, molecular carbon C₂₀₄ featuring 12-fold [5]helicenes around four cores was successfully constructed by using nine perylene diimide (PDI) units, and exhibits good solubility and stability. Despite 256 possible stereoisomers caused by the 12-fold [5]helicenes, we only obtained one pair of enantiomers with D₃ symmetry. There are four possible pairs of enantiomers with D₃ symmetry, namely 7A, 7B, 7C and 7D. Theoretical and experimental results verify that the obtained structure belongs to 7C, which has the lowest energy. The enantiomers can also be separated by chiral HPLC. These results suggest that choosing PDIs as building blocks can not only improve the solubility and stability but also realize the stereoselectivity and chirality of molecular carbons.

Keywords: Chirality; Helicene; Molecular Carbon; Stereoisomers; Stereoselectivity.

Abstract

Grants and funding