0000000000423607
AUTHOR
Sebastian Stappert
showing 4 related works from this author
Positional Isomers of Chromophore–Peptide Conjugates Self-Assemble into Different Morphologies
2018
Ordering π-systems into defined supramolecular structures is important for the development of organic functional materials. In recent years, peptides with defined secondary structures and/or self-assembly properties were introduced as powerful tools to order peptide-chromophore conjugates into different morphologies. This work explores whether or not the directionality of peptides can be used to control the self-assembly. The position of the π-system in conjugates between oligoprolines and perylene monoimide (PMI) chromophores was varied by attaching the PMI moiety to the second-to-last residue from the C- and N-termini, respectively. Microscopic and diffraction analysis revealed that the p…
(o-Phenyleno)naphthalene diimides: a pink fluorescent chromophore
2017
(o-Phenyleno)naphthalene dianhydride 7 was synthesized by a six-step reaction. Imidizations of 7 led to various diimides 8. Their optical and electrochemical properties hold promise for organic electronics.
Practical Syntheses of Terrylene Chromophores from Naphthalene and Perylene Building Blocks
2017
A facile and efficient method to synthesize terrylene imides, a unique class of chromophores, and their derivatives from commercially available naphthalene and perylene building blocks is reported. We developed an extremely efficient Suzuki/C-H-arylation coupling cascade with Pd2(dba)3/PCy3 (dba = dibenzylidenacetone, Cy = cyclohexyl) as the catalyst and highly soluble naphthalene derivatives as starting materials. This efficiency allows purification via precipitation and crystallization, avoiding time-consuming column chromatography. For the first time, the highly soluble 3,4,11,12-terrylene tetraester was prepared in gram scale with yields up to 75 % which thus becomes a versatile startin…
Synthesis of an Acceptor–Donor–Acceptor Multichromophore Consisting of Terrylene and Perylene Diimides for Multistep Energy Transfer Studies
2016
Motivated by the results obtained from the investigation of singlet–singlet annihilation in a linear multichromophore comprising terrylene diimides (TDI) and perylene diimide (PDI) in 2010, we report the detailed process toward the successful synthesis of a TDI–PDI–TDI dyad. Ineffective synthetic pathways, which were necessary for the understanding of the step-by-step construction of the complex multichromophore, are described, leading toward a universal synthetic plan for multicomponent systems containing rylene diimides separated by rigid oligophenylene spacers.