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A Visual Demonstration of Supramolecular Chemistry: Observable Fluorescence Enhancement upon Guest-Host Inclusion

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Brian D. Wagner , Penny J. MacDonald and Maryam Wagner

Department of Chemistry, University of Prince Edward Island, Charlottetown, PEI C1A 4P3, Canada

Thomas A. Betts

Department of Chemistry, Kutztown University, Kutztown, PA 19530

J. Chem. Educ., 2000, 77 (2), p 178

DOI: 10.1021/ed077p178

Publication Date (Web): February 1, 2000

Section:

History, Education, and Documentation

Abstract

Supramolecular chemistry, or "chemistry beyond the molecule", is an increasingly important area of modern chemical research. It deals with highly organized structures involving two or more individual molecules held together by intermolecular forces. Supramolecular host-guest inclusion complexes refer to structures in which a smaller "guest" molecule is held within the internal cavity of a larger "host" molecule. Supramolecular systems have widespread practical applications to various areas of chemistry, including catalysis, molecular sensors and chemical separations. In this article, we describe a simple yet striking demonstration of supramolecular host-guest inclusion and fluorescence based on the extraordinarily large observed fluorescence enhancement of the probe ANS by a modified ß-cyclodextrin. The fluorescence enhancement is readily observable by the naked eye. This demonstration is appropriate for an advanced organic or physical chemistry class and requires only a simple hand-held UV lamp as the excitation source.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Demonstrations

Keywords (Feature):

Tested Demonstrations

Keywords (Subject):

Photochemistry

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

Fluorescent Dyes and Their Supramolecular Host/Guest Complexes with Macrocycles in Aqueous Solution
Roy N. Dsouza, Uwe Pischel, and Werner M. Nau
Chemical Reviews2011 111 (12), 7941-7980
- Fluorescent Dyes and Their Supramolecular Host/Guest Complexes with Macrocycles in Aqueous Solution
  Roy N. Dsouza, Uwe Pischel, and Werner M. Nau
  Chemical Reviews2011 111 (12), 7941-7980
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Supramolecular Inclusion in Cyclodextrins: A Pictorial Spectroscopic Demonstration
Basudeb Haldar , Arabinda Mallick and Nitin Chattopadhyay
Journal of Chemical Education2008 85 (3), 429
- Supramolecular Inclusion in Cyclodextrins: A Pictorial Spectroscopic Demonstration
  Basudeb Haldar , Arabinda Mallick and Nitin Chattopadhyay
  Journal of Chemical Education2008 85 (3), 429
  A spectroscopic experiment is presented that reveals that the hydrophobically end-modified water-soluble polymeric fluorophore, pyrene end-capped poly(ethylene oxide) (PYPY), interacts differently with α, β, and γ-cyclodextrins (CD) to form supramolecular ...
  Abstract | Hi-Res PDF | PDF w/ Links
Use of the Mid-Lecture Break in Chemistry Teaching: A Survey and Some Suggestions
David K. Smith
Journal of Chemical Education2006 83 (11), 1621
- Use of the Mid-Lecture Break in Chemistry Teaching: A Survey and Some Suggestions
  David K. Smith
  Journal of Chemical Education2006 83 (11), 1621
  This article uses student feedback to explore student attitudes towards the use of lecture breaks. The survey illustrates that undergraduates genuinely value such breaks, finding them educationally useful and enhancing their enjoyment of the lecture ...
  Abstract | Hi-Res PDF | PDF w/ Links
Classroom Demonstrations of Concepts in Molecular Fluorescence
Jonathan P. Blitz , Daniel J. Sheeran and Thomas L. Becker , Neil D. Danielson
Journal of Chemical Education2006 83 (5), 758
- Classroom Demonstrations of Concepts in Molecular Fluorescence
  Jonathan P. Blitz , Daniel J. Sheeran and Thomas L. Becker , Neil D. Danielson
  Journal of Chemical Education2006 83 (5), 758
  A multichannel CCD-array spectrophotometer and handheld UV lamp are utilized to acquire and project in real-time the fluorescence emission spectra of quinine, fluorescein, eosin yellow, and rhodamine B. Instrumental concepts of fluorescence are ...
  Abstract | Hi-Res PDF | PDF w/ Links
A Template-Controlled Solid-State Reaction for the Organic Chemistry Laboratory
Tomislav Friscic , Tamara D. Hamilton , Giannis S. Papaefstathiou and Leonard R. MacGillivray
Journal of Chemical Education2005 82 (11), 1679
- A Template-Controlled Solid-State Reaction for the Organic Chemistry Laboratory
  Tomislav Friscic , Tamara D. Hamilton , Giannis S. Papaefstathiou and Leonard R. MacGillivray
  Journal of Chemical Education2005 82 (11), 1679
  An undergraduate laboratory experiment that employs molecules, in the form of linear hydrogen-bond templates, to direct the [2 + 2] photodimerization in the solid state is described. The experiment introduces the undergraduate students to supramolecular ...
  Abstract | Hi-Res PDF | PDF w/ Links