Synthesis, optoelectronic properties and hydrogen-bond promoted organisation of heteroatom-doped polycyclic hydrocarbons

Student thesis: Doc typesDoctor of Sciences


The first part of this research thesis is mainly focused on the synthesis and study of novel chromophores derived from peri-xanthenoxanthene (PXX), an O-doped derivative of anthanthene. This structure was chosen due to its promising properties in organic electronic such as it integration in transistor used in the first rollable display developed by Sony. In the second part, two methods on the organizational control of chromophores, by either hydrogen bonding or gel encapsulation will be discussed.
First, Chapter 1 describes a brief overview of polyaromatics hydrocarbons (PAHs) based organoelectronic along with a summary of the different ways to engineer the frontier orbital energy levels as well as the solid-state organization of PAH.
In the first part of Chapter 2, general aspect on diaryl ether formation is described followed by a general description of the current state of the art of the synthesis and derivatization of PXX. The second part of this chapter will discuss about the synthesis, solid-state arrangement and electrochromic properties of electron-enriched PXX functionalised with hexyloxy chains on their periphery.
Chapter 3 will discuss the incorporation of PXX in charge separation application as an electron donating moiety. In this context, PXX bearing one or two fullerene-C60 have been synthetised and their photophysical properties have been determined by Dr. Andrea Fermi (a former member of the group) and in collaboration with Meditecknology at the “CNR Area della Ricerca di Bologna”.
Chapter 4 aims to describe the synthesis and photophysical characterization of peri-thiaxanthenothiaxanthene PTXTX, a S-doped version of PXX. In this case, the successful synthesis of PTXTX was obtained by Oliwia Matuszewska and the properties were determined by Tomasso Battisti (both from the group).
Chapter 5 is dedicated to the study of hydrogen bonding promoted by boronic acid. This chapter starts with brief introduction of hydrogen bonding as well as the state of the art of boronic acids H-bonding properties. Then, a seminal study performed by Dr. Irene Georgiou, Dr. Simon Kervyn and Dr. Federica De Leo concerning solution and solid-state binding studies between arylboronic acid and 1,8-naphthyridine (NAP), 1,10-phenanthroline (Phen) or 5,6,11,12-tetraazanaphthacene (TANP), resulting in dimeric, trimeric or polymeric species, is described. Finally, tuning of the H-bond properties of both arylboronic acid and TANP, forming a graphene-like supramolecular arrangement, is investigate.
Finally, Chapter 6 deals with the magnetic alignment of poly(3-hydroxybutyric acid-co-3-hydroxyvaleric) acid PHBV organogel and incorporation of chromophores in the polarized materials.
Date of Award6 Jul 2020
Original languageEnglish
Awarding Institution
  • University of Namur
SponsorsFund for Research Training in Industry and Agriculture (FRIA)
SupervisorStephane Vincent (Supervisor), Davide BONIFAZI (Supervisor), Carmela Aprile (Jury), Stephane Vincent (Jury), Pascal Gerbaux (Jury) & Milan Kivala (Jury)

Cite this