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Photo-Induced Energy or Electron Transfer in Supramolecular Systems: Applications to Molecular Wires and Light-Harvesting Sensors

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Raymond F. Ziessel

Laboratorie de Chimie, d''Electronique et de Photonique Moleculaires, Ecole de Chimie, des Polymeres et des Materiaux de Strasbourg (ECPM), 1, rue Blaise Pascal, 67008 Strasbourg, France

J. Chem. Educ., 1997, 74 (6), p 673

DOI: 10.1021/ed074p673

Publication Date (Web): June 1, 1997

Section:

History, Education, and Documentation

Abstract

A synthetic protocol is summarized that provides access to various multi-site ligands (bipyridines, terpyridines...) bridged by alkyne spacer comprising one to four ethynyl subunits. These ditopic ligands have been used to prepare luminescent transition-metal complexes in which long-range electronic coupling between remote units has been observed. Intramolecular triplet energy transfer, photon migration and light-induced electron transfer occur by way of extremely rapid superexchange involving energetic states localized on the bridge. Very long triplet-energy excited-state have been measured in the terpyridine complexes resulting from a selective decoupling of the MLCT triplet state and higher-energy metal-centered (MC) and ligand-centered excited states (LC). The level of electronic communication along the molecular wire can be modulated by insertion of "Pt(PⁿBu₃)₂" insulating groups into the bridge. These metallo-insulating groups provide further means to manipulate the stereochemistry around the central subunit and to control the efficiency of triplet energy transfer. A photochemical molecular device consisting of a light conversion process, via an absorption/energy-transfer/emission (A/ET/E) sequence of photochemical events is realized in photoactive lanthanide complexes of calix[4]arenes podands bearing three to four pendant bipyridine arms.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Inorganic Chemistry

Keywords (Feature):

Symposium Report

Keywords (Subject):

Materials Science

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This article has been cited by 16 ACS Journal articles (5 most recent appear below).

A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway
Stéphane Diring, Pascal Retailleau, and Raymond Ziessel
The Journal of Organic Chemistry2007 72 (26), 10181-10193
- A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway
  Stéphane Diring, Pascal Retailleau, and Raymond Ziessel
  The Journal of Organic Chemistry2007 72 (26), 10181-10193
  A generic design principle for the preparation of a variety of substituted phenylpolypyridine ligands is described. These ligands are readily prepared by a regioselective [4+2] cycloaddition between electron-deficient dienes, such as 2,6-disubstituted-1,...
  Abstract | Full Text HTML | Hi-Res PDF
A Concise Modular Synthesis of 2,5-Diethynyl-3,4-dibutyl-thiophene-Bridged Back-to-Back Terpyridine Ligands
Celine Ringenbach, Antoinette De Nicola, and Raymond Ziessel
The Journal of Organic Chemistry2003 68 (12), 4708-4719
- A Concise Modular Synthesis of 2,5-Diethynyl-3,4-dibutyl-thiophene-Bridged Back-to-Back Terpyridine Ligands
  Celine Ringenbach, Antoinette De Nicola, and Raymond Ziessel
  The Journal of Organic Chemistry2003 68 (12), 4708-4719
  The efficient synthesis of soluble and rigid terpyridine-based ditopic ligands bearing an increasing number of 2,5-diethynyl-3,4-dibutylthiophene (DEDBT) modules has demonstrated the advantages of a single convergent strategy based on a double coupling in ...
  Abstract | Full Text HTML | Hi-Res PDF
New Ligands Bearing Chiral Bioactive Fragments
Abderrahim Khatyr and Raymond Ziessel
Organic Letters2001 3 (12), 1857-1860
- New Ligands Bearing Chiral Bioactive Fragments
  Abderrahim Khatyr and Raymond Ziessel
  Organic Letters2001 3 (12), 1857-1860
  Reliable and practical synthetic routes for the construction of hybrid molecules bearing both a chelating center and a useful biofunction are presented. They comprise the sequential cross-coupling reaction between ethynylated synthons with iodo-...
  Abstract | Full Text HTML | Hi-Res PDF
Synthesis of Quasi-Linear and Segmented Bis- to Penta-2,2‘-bipyridine Polytopic Ligands Built via a Convergent Approach
Abderrahim Khatyr and Raymond Ziessel
The Journal of Organic Chemistry2000 65 (23), 7814-7824
- Synthesis of Quasi-Linear and Segmented Bis- to Penta-2,2‘-bipyridine Polytopic Ligands Built via a Convergent Approach
  Abderrahim Khatyr and Raymond Ziessel
  The Journal of Organic Chemistry2000 65 (23), 7814-7824
  Reliable and practical routes for the preparation of segmented oligomeric 2,2-bipyridine-based ligands possessing rigid and conjugated spacers are presented. The first series of ligands bears a single alkyne function as a bridge and has been built by Pd(...
  Abstract | Full Text HTML | Hi-Res PDF
Facile Synthesis of Polypyridine Esters: A Route to Functionalized Aldehydes
Abdelkrim El-ghayoury and Raymond Ziessel
The Journal of Organic Chemistry2000 65 (23), 7757-7763
- Facile Synthesis of Polypyridine Esters: A Route to Functionalized Aldehydes
  Abdelkrim El-ghayoury and Raymond Ziessel
  The Journal of Organic Chemistry2000 65 (23), 7757-7763
  A wide range of ester-substituted oligopyridines, based on pyridine, 1,8-naphthyridine, 1,10-phenanthroline, 2,2-bipyridine, and 2,2:6,6-terpyridine units, has been synthesized and fully characterized. The principal reaction involves the palladium(0)...
  Abstract | Full Text HTML | Hi-Res PDF