Precrystalline Aggregates Enable Control over Organic Crystallization in Solution

Chen Shahar, Sounak Dutta, Haim Weissman, Linda J.W. Shimon, Holger Ott, Boris Rybtchinski

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Understanding and controlling organic crystallization in solution is a long-standing challenge. Herein, we show that crystallization of an aromatic amphiphile based on perylene diimide in aqueous media involves initially formed amorphous spherical aggregates that evolve into the crystalline phase. The initial appearance of the crystalline order is always confined to the spherical aggregates that are precursors for crystalline evolution. The change in the solvation of the prenucleation phase drives the crystallization process towards crystals that exhibit very different structure and photofunction. The initial molecular structure and subsequent crystal evolution can be regulated by tuning the hydrophobicity at various stages of crystallization, affording dissimilar crystalline products or hindering crystallization. Thus, the key role of the precrystalline states in organic crystal evolution enables a new strategy to control crystallization by precrystalline state manipulation.

Original languageEnglish
Pages (from-to)179-182
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number1
DOIs
Publication statusPublished - Jan 4 2016

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Keywords

  • crystallization
  • hydrophobic interactions
  • perylene diimide
  • polymorphism
  • prenucleation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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