π-π interactions in self-assembly

Christian G. Claessens, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalReview article

337 Scopus citations

Abstract

The recent surge of interest in the control of molecular organization in both the solution state (i.e. self-assembly) and the solid state (i.e. crystal engineering) has led researchers to recognize increasingly the importance of weak non-covalent interactions. The design and synthesis of an efficient molecular construction set are dependent upon a very close interplay between x-ray crystallography and synthetic chemistry. π-π Stacking interactions between π-donors, such as hydroquinone, resorcinol or dioxynaphthalene residues, and π-accepting ring systems, such as bipyridinium or π-extended viologen units, can govern the self-assembly of a variety of complexes and interlocked molecular compounds in both the solid and solution states. Non-covalent bonding interactions (i.e. π-π interactions) can be considered as information vectors: they define and rule the self-assembly processes that lead to the formation of the desired molecular and supramolecular architectures, and thereafter they still govern the dynamic processes occurring within the self-assembled structures and superstructures. The manner in which such molecules and supermolecules can contribute to an understanding of non-covalent interactions at both structural and superstructural levels is described, with reference to numerous examples of self-assembly processes in synthesis, of dynamic processes in the solution state, and of the packing of molecules and molecular complexes in the solid state.

Original languageEnglish (US)
Pages (from-to)254-272
Number of pages19
JournalJournal of Physical Organic Chemistry
Volume10
Issue number5
DOIs
StatePublished - Jan 1 1997

Keywords

  • Catenanes
  • Cyclophanes
  • Self-assembly
  • π-π interactions

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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