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Synthesis and Surface Behaviour of NDI Chromophores Mounted on a Tripodal Scaffold: Towards Self-Decoupled Chromophores for Single-Molecule Electroluminescence

Balzer, Nico 1; Lukášek, Jan 1; Valášek, Michal 1; Rai, Vibhuti ORCID iD icon 2; Sun, Qing ORCID iD icon 2; Gerhard, Lukas 2; Wulfhekel, Wulf 2; Mayor, Marcel 1
1 Institut für Nanotechnologie (INT), Karlsruher Institut für Technologie (KIT)
2 Institut für QuantenMaterialien und Technologien (IQMT), Karlsruher Institut für Technologie (KIT)


This paper reports the efficient synthesis, absorption and emission spectra, and the electrochemical properties of a series of 2,6-disubstituted naphthalene-1,4,5,8-tetracarboxdiimide (NDI) tripodal molecules with thioacetate anchors for their surface investigations. Our studies showed that, in particular, the pyrrolidinyl group with its strong electron-donating properties enhanced the fluorescence of such core-substituted NDI chromophores and caused a significant bathochromic shift in the absorption spectrum with a correspondingly narrowed bandgap of 1.94 eV. Cyclic voltammetry showed the redox properties of NDIs to be influenced by core substituents. The strong electron-donating character of pyrrolidine substituents results in rather high HOMO and LUMO levels of -5.31 and -3.37 eV when compared with the parental unsubstituted NDI. UHV-STM measurements of a sub-monolayer of the rigid tripodal NDI chromophores spray deposited on Au(111) show that these molecules mainly tend to adsorb flat in a pairwise fashion on the surface and form unordered films. However, the STML experiments also revealed a few molecular clusters, which might consist of upright oriented molecules protruding from the molecular island and show electroluminescence photon spectra with high electroluminescence yields of up to 6×10$^{-3}$. ... mehr

Verlagsausgabe §
DOI: 10.5445/IR/1000136145
Veröffentlicht am 12.08.2021
DOI: 10.1002/chem.202101264
Zitationen: 3
Web of Science
Zitationen: 3
Zitationen: 3
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Nanotechnologie (INT)
Physikalisches Institut (PHI)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000136145
HGF-Programm 43.32.01 (POF IV, LK 01) Molecular Materials Basis for Optics & Photonics
Weitere HGF-Programme 47.11.05 (POF IV, LK 01) Towards Quantum and Neuromorphic Computing Functionalities
Erschienen in Chemistry - A European Journal
Verlag John Wiley and Sons
Band 27
Heft 47
Seiten 12144-12155
Vorab online veröffentlicht am 21.06.2021
Nachgewiesen in Scopus
Web of Science
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