Crystallization of Organic Molecules: Nonclassical Mechanism Revealed by Direct Imaging

ACS Central Science
Yael TsarfatiBoris Rybtchinski

Abstract

Organic crystals are of primary importance in pharmaceuticals, functional materials, and biological systems; however, organic crystallization mechanisms are not well-understood. It has been recognized that "nonclassical" organic crystallization from solution involving transient amorphous precursors is ubiquitous. Understanding how these precursors evolve into crystals is a key challenge. Here, we uncover the crystallization mechanisms of two simple aromatic compounds (perylene diimides), employing direct structural imaging by cryogenic electron microscopy. We reveal the continuous evolution of density, morphology, and order during the crystallization of very different amorphous precursors (well-defined aggregates and diffuse dense liquid phase). Crystallization starts from initial densification of the precursors. Subsequent evolution of crystalline order is gradual, involving further densification concurrent with optimization of molecular ordering and morphology. These findings may have implications for the rational design of organic crystals.

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Citations

Sep 27, 2019·Angewandte Chemie·Eduard WiedenbeckHelmut Cölfen
Jan 26, 2021·Beilstein Journal of Organic Chemistry·Chen ShaharBoris Rybtchinski
Feb 27, 2021·The Journal of Physical Chemistry. a·Yu GongMing Hu
Mar 3, 2021·Proceedings of the National Academy of Sciences of the United States of America·Xiangwen LiuUtkur Mirsaidov
Apr 30, 2021·Journal of the American Chemical Society·Jonas MaternGustavo Fernández
Jun 4, 2021·ACS Central Science·Yael TsarfatiBoris Rybtchinski
Sep 4, 2019·Accounts of Chemical Research·Elisha KriegBoris Rybtchinski
Jun 29, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Fuyuki ItoShiho Katsumi
Jun 8, 2019·Journal of the American Chemical Society·Marie JehanninHelmut Cölfen
Aug 20, 2019·Journal of the American Chemical Society·Jesús Del BarrioOren A Scherman
Aug 19, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Tamar Nicole SoussanaRan Drori

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Methods Mentioned

BETA
electron microscopy
transmission electron microscopy
X-ray
electron diffraction

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