ORGANIC CHEMISTRY OF MATERIALS
Learning outcomes of the course unit
Knowledge and understanding: the main goal is to provide to the student the tools for the comprehension and the dissertation of bulk materials, hybrid materials and nanomaterilas using the concepts acquired in organic chemistry; particular attention will be paid to the influence of the structure-activity relationship, and to modern organic reactions allowing to tailor material properties.
Learning skills: students will acquire the specific language of the material chemistry field and will achieve the ability to correlate the various aspects of materials, from basic chemical properties to technological applications.
In particular, at the end of the course the student will be able to:
• recognize the synthetic techniques and to carry out the structural characterization of organic materials and of organic /inorganic hybrid materials
• correlate the structure and the properties of organic materials even in complex systems;
• critically understand a problem related to his profession and to propose specific solutions;
• design and complete an experiment through individual or team activities.
• retrieve bibliographic information to plan and carry out the synthesis of organic materials and organic /inorganic hybrid materials.
• collect and interpret experimental data in the laboratory;
• set up experimental activities;
• organize team-work;
• adapt to different work areas and issues;
• deliberates on important scientific and ethical issues.
• communicate chemical problems in a written and verbal form, even with the help of multimedia systems;
• sustain a contradictory on issues related to his studies;
• interact with people in multidisciplinary projects;
• carry out experimental training activities for undergraduate students.
• retrieve information from literature, databases and on the internet;
• learn independently, addressing new scientific issues or professional problems;
• continue to study solutions to complex problems, including interdisciplinary ones, finding the information needed to formulate answers and knowing how to defend their own proposals in specialized and non-specialized contexts.
Knowledge of the concepts developed in the Organic Chemistry 1, Organic Chemistry 2 and in the Chemistry and technology of polymeric material courses
Course contents summary
In the first part of the course, the degradation and resistance of organic materials will be discussed, with focus on reactions under extreme conditions. Scale for describing extreme acid or extreme basic conditions will be introduced. Oxidation, pyrolysis and combustion and methods for prevention will be described. The properties of organic materials relevant for applications, and their connection with the molecular structure and with intermolecular non-covalent interactions will be then illustrated.
Finally, strategies for tailored modification of bulk materials, interfaces, and organic nanomaterials will be discussed.
In the second part of the course, the synthetic techniques for the preparation of organic materials for electronics and photonics will be introduced, with a rundown on the main structural factors that affect the properties of these compounds. The classes of molecules and the strategies used for the preparation of organic materials on surfaces will be then illustrated. In the final part of the course, the synthesis and properties of an emerging class of organic materials, the Carbon Quantum Dots (C-dots) will be presented.
A - Reactivity (2 CFU) Recalls on the structure of the main organic materials and their diffusion. Kinetics of reactions in the Chemistry of organic materials. Thermal decomposition and pyrolysis. Use of pyrolysis reactions in the analysis and in the manufacture of materials (carbon fibers). Oxidation, self-oxidation and photo-oxidation of organic materials. combustion. Principles of photochemical reactions. Photodegradation and photostability. Extreme acidic or basic conditions: effects on the various classes of compounds. Acidity and basicity scales in non-aqueous solvents. Material transformation strategies (bulk or surface modification). Biodegradability and reversibility of materials.
B - Properties (1 CFU) Properties dependent on the structure. Mechanical properties. Stereochemical properties of materials. Polymeric elicity. Intermolecular interactions, adaptive supramolecular materials. Solubility: solvent descriptors and theories. Swelling and gel formation. biodegradability. Self-repair. Adhesiveness and main classes of molecular and supramolecular adhesives. Biointerphase and anti-fouling properties.
C - Organic materials for photonics and electronics (1 CFU)
Properties of organic materials for electronics (basic electronic properties, donor and acceptor groups, stability and processability). Synthesis of conjugated systems using alkene forming reactions and by organometallic compounds. Synthesis of donors and acceptors. Polymerization reactions.
D - Self-assembly of organic molecules in nanostructures (1 CFU)
Chemical reactions for the synthesis of organic nanomaterials on surfaces (Ulmann Coupling, condensation, polymerization and bioconjugation reactions). Methods to promote self-assembly of organic structures on surfaces (Langmuir-Blodgett techniques, layer-by-layer aggregation, self-assembly in solution). Molecular design and building blocks (amphiphilic molecules, gelators, pi-systems, dendrimers). Self-assembly on inorganic materials.
E - Carbon-based nanomaterials (1CFU)
Synthesis, characterization and physical properties, applications in bioimaging, sensing of carbon nanotubes, fullarenes, graphene and carbon dots in materials science.
Sources for in-depth study
Springer Science & Business Media 2011
Functional Hybrid Materials
Editor: P. Gomez-Romero, C. Sanchez
Editor: G. Kickelbick
Eric V. Anslyn, Dennis A. Daugherty: Modern Physical Organic Chemistry, University Science Books, 2006
F.A. Carey e R.J. Sundberg Advanced Organic Chemistry 5th Edition, Springer, 2007
J. March Advanced Organic Chemistry Reactions, Mechanisms, and Structure , 7th Edition John Wiley & Sons , 2013
Oral lectures in person The recorded lectures will be made available on-line on the platform ELLY.
Assessment methods and criteria
The exam consists of presentation by the student on a topic of the course, followed by a written and an oral tests.
The knowledge required to pass the exam are:
Demonstration of knowledge and understanding, supported by basic knowledge of Organic Chemistry, in applying these concepts to Materials Chemistry with professional attitude and originality. Ability to apply knowledge of Organic Chemistry of Materials in a broader and multidisciplinary context, understanding the links with other subject of the Chemistry Master Degree; maturity and knowledge necessary to undertake further studies with a self-directed degree of autonomy
Demonstration of knowledge of the structure and reactivity of bulk organic materials, hybrid materials and organic nanomaterials and their applications. Knowledge of relationships between structure and properties of organic materials.
Knowledge of main transformations and reactivity of organic materials and of synthetic methods for their tailored modification.
The written exam consists of 3 questions, under the form of case-studies. It is passed if 2/3 questions are answered correctly or, alternatively, if at least 60% of the total content expressed is correct and comprehensive.
The oral examination consists of the discussion of the written exam with a deepening of the theoretical part, in particular aspects not included in the written exam.
Teacher's handouts will be available in various formats in the web site.