Orthogonality in organic, polymer, and supramolecular chemistry: From Merrifield to click chemistry

Chun Ho Wong, Steven C. Zimmerman

Research output: Contribution to journalArticlepeer-review

244 Scopus citations


The concept of orthogonality has been applied to many areas of chemistry, ranging from wave functions to chromatography. But it was Barany and Merrifield's orthogonal protecting group strategy that paved the way for solid phase peptide syntheses, other important classes of biomaterials such as oligosaccharides and oligonucleotides, and ultimately to a term in widespread usage that is focused on chemical reactivity and binding selectivity. The orthogonal protection strategy has been extended to the development of orthogonal activation, and recently the click reaction, for streamlining organic synthesis. The click reaction and its variants are considered orthogonal as the components react together in high yield and in the presence of many other functional groups. Likewise, supramolecular building blocks can also be orthogonal, thereby enabling programmed self-assembly, a superb strategy to create complex architectures. Overall, orthogonal reactions and supramolecular interactions have dramatically improved the syntheses, the preparation of functional materials, and the self-assembly of nanoscale structures.

Original languageEnglish
Pages (from-to)1679-1695
Number of pages17
JournalChemical Communications
Issue number17
StatePublished - 31 Jan 2013
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry (all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry


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