2021
DOI: 10.1002/chem.202101264
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Synthesis and Surface Behaviour of NDI Chromophores Mounted on a Tripodal Scaffold: Towards Self‐Decoupled Chromophores for Single‐Molecule Electroluminescence

Abstract: 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 … Show more

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Cited by 3 publications
(14 citation statements)
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References 66 publications
(184 reference statements)
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“…Naphthalene diimides are compact, planar, and stable chromophores with electronic and optical properties that can be adjusted by the core substituents 23 , 30 , thus finding promising applications in optoelectronic devices 31 . The intention of the molecular design is to fix the chromophore upright on the substrate, minimizing its interaction with the surface.…”
Section: Resultsmentioning
confidence: 99%
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“…Naphthalene diimides are compact, planar, and stable chromophores with electronic and optical properties that can be adjusted by the core substituents 23 , 30 , thus finding promising applications in optoelectronic devices 31 . The intention of the molecular design is to fix the chromophore upright on the substrate, minimizing its interaction with the surface.…”
Section: Resultsmentioning
confidence: 99%
“…The NDI dyes were identified as the ideal optically active subunit due to their robustness, optical tunability, structural integrity, and synthetic accessibility. In the first series of NDIs mounted on a smaller tripodal platform based on tris( meta -sulfanylphenyl)methane 23 , the physisorption of the chromophore efficiently competed with the intended fixation by the three foot subunits of the tripod, pointing at the subtle balance between the surface interactions involved 23 . As the size of the chromophore in the presently reported second series remains the same, the foot structure was enlarged by three tolane subunits, increasing its lateral dimension and thus also its interaction with the surface.…”
Section: Resultsmentioning
confidence: 99%
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“…In recent years, luminescence, i.e., photoemission, from organic molecules on metals, has gained considerable interest for its potential applications in the display and lighting industries [97][98][99]. However, when molecules are directly adsorbed on or very close to metal surfaces, the intrinsic molecular fluorescence is often quenched by the strong interaction between the molecules and the substrate [100].…”
Section: Photoemission In Mjsmentioning
confidence: 99%