cod. 1004772

Academic year 2014/15
1° year of course - First semester
Academic discipline
Chimica organica (CHIM/06)
Discipline chimiche organiche
Type of training activity
48 hours
of face-to-face activities
6 credits
hub: PARMA
course unit

Learning objectives

Knowledge and understanding: To acquire the knowledge necessary to understand the theoretical basis and the experimental details of research works aimed at the design and obtainment of new molecular receptors, at the study of the efficiency and selectivity in the complexation of molecular species and at the obtainment of devices that exploit weak intermolecular interactions.
The development of the ability to understand in details of molecular recognition phenomena also in the biomolecular field will be also stimulated in the students.

Applying knowledge and understanding: Ability to analyse the supramolecular structure between a receptor and a substrate, to understand the interactions and the forces involved in the complex formation and predict the properties of the supermolecule generated.

Capacità di utilizzare le conoscenze acquisite per progettare nuovi recettori e materiali molecolari con proprietà innovative.

Making judgements: the student should acquire a complete independence in the identification of the complementarity and preorganization degree of a host for a guest and in the determination of the most appropriate synthetic routes to a macrocyclic compound or to a self-assembled entity.

Communication: the student will be stimultate to communicate by using a proper terminology for a supramolecular chemist and will be needed to be able to discuss a literature paper on a specific argument of supramolecular chemistry.

Lifelong learning skills: the stident will also acquire the ability to interpret the results of an experimental study in the field of supramolecular chemistry in terms of molecular and supramolecular properties of the complexes.


To fruitfully follow the course it is fundamental to have a solid knowledge of General
Chemistry, Physical Chemistry and Organic Chemistry.

Course unit content

Introduction to Supramolecular Chemistry. The molecular recognition phenomena.
Intermolecular forces.

Methods for the determination of stoichiometries and stabilities of the complexes.
Methods for the synthesis of macrocyclic compounds.
Cation complexation.
Anion complexation.
Complexation of neutral molecules.
Supramolecular catalysis.
Applications of Supramolecular Chemistry to Drug-discovery.

Full programme

Introduction to Supramolecular Chemistry. Molecular recognition. Intermolecular
forces. Methods for the determination of the stoichiometries of the complexes and of
the complexation constants via different techniques (NMR, UV-vis, fluorescence,
calorimetry, potentiometry,...). Extraction percentage and distribution coefficients.
Methodologies for the synthesis of macrocyclic compounds (crown, aza-crown,
calixarenes, resorcarenes, cyclodextrins). Synthestic modifications of the
Cation complexation with crown-ethers, cryptands, spherands and ciclophanes:
synthetic methodologies and complexation studies. Applications in the field of
imaging (MRI, luminescent probes , radiolabelling), of radiotherapeutics, of metal
detoxification and of the treatment of radioactive and heavy metals waste.
Neutral molecules complexation with crown-ethers, cyclodextrins and cyclophanes:
studies on the complexes, thermodynamic and kinetic parameters, effect of the
structure of the guest and of the solvent: the hydrophobic effect.
Anion complexation by natural and synthetic receptors.
Self-assembly. Supramolecular catalysis.
Cavitands from cyclotriveratrylene, resorcarenes and calixarenes in molecular
recognition. Calixarenes as molecular platform for the synthesis of receptors for
cations, anions and neutral molecules.
Discussion on some application in the field of Supramolecular Science: Ionselective
Electrodes (ISE), ion-selective membranes, chromoionophores,
piezoelectric and fluorescence sensors.
Supramolecular Catalysis.
Bioorganic supramolecular chemsitry.


The following book represents a fair introduction to supramolecular chemistry.
Supramolecular Chemistry, P.D. Beer, P. A. Gale, D.K. Smith, Oxford University
Primers, OUP, 1999.
For several topics should however be implemented with the following
monographies:Supramolecular Chemistry: From Molecules to Nanomaterials, J. W. Steed, P. A. Gale, Wiley 2012 (ISBN: 978-0-470-74640-0); Supramolecular Chemistry: Concepts and Perspectives. J.-M. Lehn, VCH Ed.,
Weinheim, 1985.
Comprehensive Supramolecular Chemistry. Executive editors Jerry L. Atwood...[et
al.] ; chairman of the editorial board Jean Marie Lehn. - [Oxford] : Pergamon, 1996.
- 11v.
Calixarenes Revisited. C.D. Gutsche, J.F. Stoddart Ed., Royal Society of Chemistry,
Cambridge, 1998.
Container molecules and their guests. D.J. Cram and J.M. Cram. - London : Royal
Society of Chemistry, 1994.
Crown ethers and cryptands. G.W. Gokel. - London : Royal Society of Chemistry,
Cyclophanes. F. Diederich. - London : Royal Society of Chemistry, 1991

Teaching methods

The student will be evaluated (oral exam only) both on the monographic part and on
the report on a literature article on a specific argument of supramolecular chemistry.

Assessment methods and criteria

Oral examination: the student will be required to report and explain a literature paper on a study dealing with Supramolecular Chemistry. Questions on selected topics of programme of the course. This will allow to verify the competence and skills acquired by the student together with his communication ability in the field of Supramolecular Chemistry.

The exam will be passed from those students which show to have acquired the ability to deeply understand the interactions at the basis of and the methodologies to study the supramolecular complexes. A knowledge of the different classes of the main supramolecular receptors will be also required.

It will be also evaluated the ability of the student to pintpoint the most efficient synthetic route for a macrocyclic or acyclic synthetic receptor (up to further 6 points).

It will be also evaluated the ability to correlate the structure of supramolecular complexes with their chemical and supramolecular properties (up to further 6 points).

Other information

The teacher is available to students for explanations and further discussion on the topics touched during the lectures in the classroom. Copies of the slides shown in the classroom and further literature material is available on the net at the page of the course. Everything can be downloaded by free.
The dates of the oral exams are also indicated on the web but additional dates can be requested by the students.