biostudies-literatureBalzer NDeutscher Akademischer AustauschdienstDeutsche ForschungsgemeinschaftHigher Education Discipline Innovation Project12144-12155https://www.ebi.ac.uk/biostudies/studies/S-EPMC8457086biostudies-literatureUnknown27(47)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 cChemistry (Weinheim an der Bergstrasse, Germany)Synthesis and Surface Behaviour of NDI Chromophores Mounted on a Tripodal Scaffold: Towards Self-Decoupled Chromophores for Single-Molecule Electroluminescence.PMC845708690002-18011002MA 2605/6-1GE 2989/2-1Rai VWulfhekel WBalzer NSun QMayor MGerhard LLukasek JValasek MfalseSynthesis and Surface Behaviour of NDI Chromophores Mounted on a Tripodal Scaffold: Towards Self-Decoupled Chromophores for Single-Molecule Electroluminescence.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 c2021-01-01T00:00:00Z2021 Aug2026-06-05T09:03:23.395Z2022-02-11T11:24:37.328ZS-EPMC84570863415204110.1002/chem.202101264