0000000000423607
AUTHOR
Sebastian Stappert
Positional Isomers of Chromophore–Peptide Conjugates Self-Assemble into Different Morphologies
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
(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
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
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.