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Porphyrinoids: Highly Versatile, Redox-Active Scaffolds for Supramolecular Design and Biomimetic Applications

Supramolecular Aspects of Chemical Biology

  1. Jonathan P. Hill1,
  2. Francis D'Souza2,
  3. Katsuhiko Ariga1

Published Online: 15 MAR 2012

DOI: 10.1002/9780470661345.smc171

Supramolecular Chemistry: From Molecules to Nanomaterials

Supramolecular Chemistry: From Molecules to Nanomaterials

How to Cite

Hill, J. P., D'Souza, F. and Ariga, K. 2012. Porphyrinoids: Highly Versatile, Redox-Active Scaffolds for Supramolecular Design and Biomimetic Applications. Supramolecular Chemistry: From Molecules to Nanomaterials. .

Author Information

  1. 1

    WPI-Center for Materials Nanoarchitectonics, Tsukuba, Japan

  2. 2

    Wichita State University, Wichita, KS, USA

Publication History

  1. Published Online: 15 MAR 2012

Abstract

Porphyrinoids are a growing class of oligopyrrole macrocycles that have structural and physical properties additional to those of the traditional tetrapyrrolic porphyrin macrocycles. In this chapter, after an initial description of how the porphyrins have been adapted for self-assembly and supramolecular synthesis, we describe several aspects of porphyrinoid supramolecular systems, finally focusing on the use of an oxoporphyrinogen core as a scaffold for assembling complex oligochromophoric manifolds by using a combination of synthetic and coordination chemistries. An important feature of porphyrinoids is their increasing amenability to core functionalization, unlike the porphyrins in which peripheral derivatization has been the usual method for augmentation. Core functionalization introduces different molecular morphological possibilities for the porphyrinoids complementary to those available for the porphyrins. In fact, porphyrins and porphyrinoids can be agglomerated in supramolecular assemblies to exploit the functional and synthetic properties of both sets of compounds.

Keywords:

  • porphyrin;
  • porphyrinoid;
  • porphyrinogen;
  • oxoporphyrinogen;
  • cyclic oligopyrrole;
  • alkylidene porphyrin;
  • self-assembly;
  • supramolecular chemistry