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Tailoring optoelectronic properties of anthanthrene through O-, S-, and N-doping

Valentini, Cataldo 2019. Tailoring optoelectronic properties of anthanthrene through O-, S-, and N-doping. PhD Thesis, Cardiff University.
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Abstract

Molecular graphenes, also known as Polycyclic Aromatic Hydrocarbons (PAHs), have been intensely studied for their application in organic electronics. However, large PAHs are poorly stable under ambient condition and, therefore, their functionalisation is crucial to obtain stable and highly efficient functional materials. Among all the possible functionalisation, the replacement of Csp2-H moiety with heteroatoms, such as oxygen, boron and nitrogen atoms, has been chosen to successfully synthesise extended PAHs. For instance, the oxygen-doped analogue of anthanthrene, named peri-xanthenoxanthene (PXX), has been studied by SONY as organic semi-conductor. In this context, the goal of our project is the synthesis and characterisation of oxygen-, nitrogen-, and sulphur-doped PXX. The opto-electronic properties of the new class of N-PXXs and S-PXX have been investigated and compared with the PXX properties. The energy band gap of N-PXX can be tuned depending upon nitrogen atoms’ position. Moreover, the nitrogen position affects the solid-state self-assembly. The N-PXX have been further modified via N-alkylation to viologen-like molecules, which are visible-light absorber with high reduction potential. The S-PXX shows a narrower band gap as compared to PXX due to the presence of an internal charge transfer. In addition, S-PXX has a strong molecular dipole which drives the solid-state organization in a lamellar π-π stacking motifs. Due to their photo-physical and solid-state organisational features, N-PXX, N-alkylated N-PXX, and S-PXX can be considered as new promising materials for optoelectronics and organic photocatalysis.

Item Type: Thesis (PhD)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 5 March 2020
Last Modified: 06 Mar 2020 11:14
URI: http://orca.cf.ac.uk/id/eprint/130150

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