Crystallization of Organic Molecules: Nonclassical Mechanism Revealed by Direct Imaging

Yael Tsarfati, Shaked Rosenne, Haim Weissman, Linda J.W. Shimon, Dvir Gur, Benjamin A. Palmer, Boris Rybtchinski

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1031-1036
Number of pages6
JournalACS Central Science
Volume4
Issue number8
DOIs
Publication statusPublished - Aug 22 2018

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Crystallization
Imaging techniques
Molecules
Densification
Crystals
Perylene
Functional materials
Aromatic compounds
Biological systems
Cryogenics
Drug products
Electron microscopy
Crystalline materials
Liquids
Pharmaceutical Preparations

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Crystallization of Organic Molecules : Nonclassical Mechanism Revealed by Direct Imaging. / Tsarfati, Yael; Rosenne, Shaked; Weissman, Haim; Shimon, Linda J.W.; Gur, Dvir; Palmer, Benjamin A.; Rybtchinski, Boris.

In: ACS Central Science, Vol. 4, No. 8, 22.08.2018, p. 1031-1036.

Research output: Contribution to journalArticle

Tsarfati, Y, Rosenne, S, Weissman, H, Shimon, LJW, Gur, D, Palmer, BA & Rybtchinski, B 2018, 'Crystallization of Organic Molecules: Nonclassical Mechanism Revealed by Direct Imaging', ACS Central Science, vol. 4, no. 8, pp. 1031-1036. https://doi.org/10.1021/acscentsci.8b00289
Tsarfati Y, Rosenne S, Weissman H, Shimon LJW, Gur D, Palmer BA et al. Crystallization of Organic Molecules: Nonclassical Mechanism Revealed by Direct Imaging. ACS Central Science. 2018 Aug 22;4(8):1031-1036. https://doi.org/10.1021/acscentsci.8b00289
Tsarfati, Yael ; Rosenne, Shaked ; Weissman, Haim ; Shimon, Linda J.W. ; Gur, Dvir ; Palmer, Benjamin A. ; Rybtchinski, Boris. / Crystallization of Organic Molecules : Nonclassical Mechanism Revealed by Direct Imaging. In: ACS Central Science. 2018 ; Vol. 4, No. 8. pp. 1031-1036.
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