97475 - Advanced Organic Synthesis for Functional Materials

Learning outcomes

At the end of the course the student has acquired the theoretical basis necessary to design and undertake the synthesis of principal molecular building blocks used in optoelectronics, the covalent fucntionalization of carbon nanoforms, sustainable C-H activation protocols, visible-light photo- and carbocatalysis.

Course contents

Prerequisites: A solid knowledge of basic organic chemistry is required, particularly regarding the synthesis and reactivity of common organic functional groups, with specific focus on the chemical manipulation of π-systems such as alkenes, alkynes, and aromatic compounds. A background in the coordination chemistry of the most common transition metals is also expected.

It is strongly recommended that students have successfully passed the exam "Organic Chemistry of Molecular Materials and Laboratory [https://www.unibo.it/it/studiare/insegnamenti-competenze-trasversali-moocs/insegnamenti/insegnamento/2025/531446] " before undertaking this course.

Course contents:

1

1. Metal catalyzed C-H bond activation

1.1. Definitions of the aliphatic and arylic C-H bond activation reaction
1.2. Mechanisms of the C-H bond activation reactions (Aromatic electrophilic substitution or oxidative insertion)
1.3. Mercuration and stannylation reactions of aromatic compounds
2.4 Ir-catalyzed borylation of aromatic compounds
1.5 Transition metal catalyzed silylation of aromatic compounds
1.6 Ruthenium catalyzed C-C bond formation reactions
1.7 Gold-catalyzed alkene and alkyne hydroarylation reactions
1.8 Palladium-catalyzed alkene and alkyne hydroarylation reactions
1.9 Cross-coupling reactions through C-H bond activation reactions

2. Covalent functionalization of carbon nano-materials

2.1 Chemistry of fullerene and analogoues
2.2 Chemistry of graphene and analogues
2.3 Carbocatalysis

3. Redox photocatalysis in organic synthesis

3.1 Basic principles of the photoredox-visible catalysis
3.2 Asymmetric photoredox catalysis
3.3 Chiral cyclometallated Ir(III) complexes: synthesis and applciation in photocatalysis

4. Electrosynthesis

4.1 Basic principles of the eChem in organic synthesis
4.2 Applications on reductive processes
4.3 Application on oxidative processes

5. Carbon dioxide as C1-bluilding block in organic synthesis

5.1 Basic concepts in CO2 reactivity
5.2 Carboxylation reactions based on CO2
5.3 Carbonylation reactions based on CO2

6. Laboratory practice

6.1 Visible-light assisted organic transformation
6.2 Electrosynthetic organic transformation

Teaching methods

• Lessons will be carried out exclusively in presence; (36 h)

• All classes will per carried out in English;

• Lab classes (8 hours) will be arrange;

• Attdenace to classes is strongly recommended but not compulsory;

 

As concerns the teaching methods of this course unit, all students must attend Module 1, 2 [https://www.unibo.it/en/services-and-opportunities/health-and-assistance/health-and-safety/online-course-on-health-and-safety-in-study-and-internship-areas] online, while Module 3 on health and safety is to be attended in class or on Microsoft Teams according to the modality chosen by the teacher. Information about Module 3 attendance schedule is available on the website of your degree programme.

Assessment methods

The exam is oral and requires the prior submission of a short written report related to the laboratory activity.

Examination modality

1) The oral examination, lasting approximately 30 minutes, begins with a PowerPoint presentation (around 10 minutes) in which the student discusses a scholarly article of their choice related to one of the topics covered in the course. The presentation is followed by a question-and-answer session, during which students may be asked about both the content of their presentation and other topics addressed throughout the course.

2) Laboratory Scientific Report. At the end of the course, each student, or a team of students, will be assigned a research article closely related to the reaction carried out during the laboratory sessions. At least 10 days before the oral examination, the student (or team) must submit a brief written report (approximately four pages) addressing the following key aspects: a concise description of the transformation presented in the article, highlighting its synthetic and/or mechanistic significance, novelty, strengths, and potential limitations. The report should also provide a comparison between the transformation described in the article and the one performed in the laboratory, emphasizing their main similarities and differences.

Overall grade

The final grade will be expressed on a 30-point scale and will be based on the evaluation of the following components:

Oral Examination (PowerPoint presentation and Q&A session)
Maximum score: 30/30

Laboratory Component, including the scientific report and the student's performance and engagement during the laboratory sessions
Maximum score: 30/30

The final grade will be calculated as a weighted average of the two scores. The oral examination will account for 80% (4/5) of the final mark, while the laboratory component will contribute 20% (1/5).

Grades

An overall grade of "not sufficient" (score < 18/30) indicates significant gaps in course content, failure to answer questions, or inadequate responses. The scores from the laboratory practice and the report are never insufficient by themselves.

An overall grade of "sufficient to fair" (18–24/30) indicates an acceptable level of preparation, but with noticeable gaps in knowledge or inadequately studied topics.

An overall grade of "good" (25–28/30) indicates that the student has a solid understanding of the course content and is able to make connections between different parts of the program. The student also successfully addressed the laboratory component and submitted a well-constructed report.

An overall grade of "excellent" (29–30/30 cum laude) indicates a thorough and in-depth preparation across the entire course program, with a clear and coherent understanding. The laboratory report is also of high quality and demonstrates extensive knowledge of the experimental techniques discussed during the practical sessions.

 

Students with learning disorders and\or temporary or permanent disabilities: please, contact the office responsible (https://site.unibo.it/studenti-con-disabilita-e-dsa/en/for-students ) as soon as possible so that they can propose acceptable adjustments. The request for adaptation must be submitted in advance (15 days before the exam date) to the lecturer, who will assess the appropriateness of the adjustments, taking into account the teaching objectives.

 

With regard to assessment, the use of AI is prohibited. Any use constitutes a violation of academic integrity.

Teaching tools

Slides will be provided to the students. No comprehensive monographs dealing with all the topics of the course are available in the market.

Course organization: 40 hours theoretical teaching - 8 hours pratical courses.

Office hours

See the website of Marco Bandini