title: Extended Polycyclic Aromatic Hydrocarbons based on Diarenoperylenes
creator: Yang, Xuan
subject: ddc-540
subject: 540 Chemistry and allied sciences
description: This thesis deals with the synthesis and investigation of larger polycyclic aromatic hydrocarbons (PAHs) obtained via π-extension of 2,10-di-tert-butyldibenzoperylene. Four types of π-extensions based on dibenzoperylene were achieved:  1. Bay region extension (Chapter 3.1): Nine cata-condensed (hetero)annulated coronenes were synthesized by a three-step approach via selective bromination of diarenoperylenes as the key-step. The influence of introducing different heteroatoms (nitrogen and sulfur) on the molecular structures as well as the photophysical and electrochemical properties were investigated.  2. L-region extension (Chapter 3.2.2): Two-fold cyclopentannulation at the L-regions and regioselective triflyloxylations have been achieved in a single step based on a dibenzoperylene. Larger contorted PAHs were obtained based on the bistriflate. The structures of the obtained contorted PAHs were studied by NMR techniques and single crystal X-ray diffraction analyses.  3. Extension at both bay and L-regions (Chapter 3.2.3): Contorted PAHs with two embedded azulene units were synthesized. The influences of the curvature on the aromaticity and the conjugation were investigated by theoretical calculations.  4. Linear extension (Chapter 3.3): Triptycene end-capped perylene oligomers with up to thirteen linearly fused benzene rings were obtained. The influence of the conjugation length on the molecular photophysical properties were studied. Regioselective brominations were achieved on these perylene oligomers and one PAH molecule with two coronene units was obtained.
date: 2021
type: Dissertation
type: info:eu-repo/semantics/doctoralThesis
type: NonPeerReviewed
format: application/pdf
identifier: https://archiv.ub.uni-heidelberg.de/volltextserverhttps://archiv.ub.uni-heidelberg.de/volltextserver/28907/1/Yang_Xuan_Dissertation_2020.pdf
identifier: DOI:10.11588/heidok.00028907
identifier: urn:nbn:de:bsz:16-heidok-289079
identifier:   Yang, Xuan  (2021) Extended Polycyclic Aromatic Hydrocarbons based on Diarenoperylenes.  [Dissertation]     
relation: https://archiv.ub.uni-heidelberg.de/volltextserver/28907/
rights: info:eu-repo/semantics/openAccess
rights: http://archiv.ub.uni-heidelberg.de/volltextserver/help/license_urhg.html
language: eng