Tetrasubstituted Peropyrenes Formed by Reductive Aromatization: Synthesis, Functionalization and Characterization.
crystallography
cyclic voltammetry
fluorescence
peropyrenes
reductive aromatization
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Aug 2021
02 Aug 2021
Historique:
received:
26
03
2021
pubmed:
26
5
2021
medline:
4
8
2021
entrez:
25
5
2021
Statut:
ppublish
Résumé
The chromophore class of 1,3,8,10-tetrasubstituted peropyrenes was effectively synthesized from peropyrenequinone via a Zn-mediated reductive aromatization approach. In one step, a symmetric functionalization of the peropyrene backbone introducing silylethers (2,3), pivaloyl (4), triflyl (5) and also phosphinite (6) groups was established. Furthermore, the potential of using 4 and 5 in transition metal catalysed cross couplings was explored leading to 1,3,8,10-tetraaryl (8-11) and tetraalkynyl (7) peropyrenes. The influence of various substituents on the optoelectronic properties of these π-system extended peropyrenes was investigated in solid state by means of X-ray crystallography, in solution by means of UV-Vis and fluorescence spectroscopy and by their redox properties studied via cyclic voltammetry. By comparison with DFT and TD-DFT calculations, it could be elucidated that introduction of a broad variety of substituents in such versatile one or two step procedures leads to peropyrenes with easily tunable HOMO and LUMO energies ranging in a gap window of 0.8 eV. The frontier molecular orbital energies identify the target molecules as promising candidates for hole transporting semiconductors.
Identifiants
pubmed: 34033166
doi: 10.1002/chem.202101101
pmc: PMC8453513
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11065-11075Subventions
Organisme : Hessisches Ministerium für Wissenschaft und Kunst
ID : PriOSS
Informations de copyright
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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