Remote Control of Dynamic Twistacene Chirality

Autor:	Si Tong Bao, Haoyu Jiang, Cedric Schaack, Shayan Louie, Michael L. Steigerwald, Colin Nuckolls, Zexin Jin
Rok vydání:	2022
Předmět:	Colloid and Surface Chemistry Solvents Stereoisomerism General Chemistry Imides Perylene Biochemistry Catalysis
Zdroj:	Journal of the American Chemical Society. 144:18772-18777
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.2c08323
Popis:	We report a reliable way to manipulate the dynamic, axial chirality in perylene diimide (PDI)-based twistacenes. Specifically, we reveal how chiral substituents on the imide position induce the helicity in a series of PDI-based twistacenes. We demonstrate that this remote chirality is able to control the helicity of flexible [4]helicene subunits by UV-vis, CD spectroscopy, X-ray crystallography, and TDDFT calculations. Furthermore, we have discovered that both the chiral substituent and the solvent each has a strong impact on the sign and intensity of the CD signals, highlighting the control of the dynamic helicity in this flexible system. DFT calculations suggest that the steric interaction of the chiral substituents is the important factor in how well a particular group is at inducing a preferred helicity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::893f1540b16ab4b041a02048baa40189 https://doi.org/10.1021/jacs.2c08323 Zobrazit plný text záznamu