Ionic Perylenetetracarboxdiimides: Highly Fluorescent and Water‐Soluble Dyes for Biolabeling

Abstract

Dying to be seen: A series of water‐soluble and highly fluorescent perylenetetracarboxdiimides (PDIs) have been synthesized in high yields by introducing charged groups into the bay region of PDI (see picture; C gray, H white, S yellow, O red). They can be used for staining living cells as they are nontoxic.

Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

“…Janelia FluorÒ 549); [16][17] however, fundamentally new types of fluorophore scaffolds could offer advantageous photophysical properties for exploitation in biological contexts. [18][19][20][21] Inspired by this prospect, we report here the first biological studies demonstrating carbon nanohoops, short macrocyclic slices of carbon nanotubes prepared by organic synthesis, as exciting new biocompatible fluorophore scaffolds (Figure 1).…”

Energy transfer in pendant perylene diimide copolymers

“…Sensitiser and acceptor perylene-acrylate monomers were synthesised using modified literature procedures, starting from commercially available 3,4,9,10-perylenetetracarboxylic dianhydride [36][37][38][39][40] (Figures 1 and 2). Creation of a polymer pendant group based on the PDI center requires an asymmetric PDI monomer.…”

Dendrimer–Metallomacrocycle Composites: Nanofiber Formation by Multi‐Ion Pairing

“…Treatment of 3,5-[bis(terpyridinyl)]phenol [34] with n-bromohexane using standard alkylation conditions (K 2 CO 3 , DMF) afforded a white microcrystalline ditopic ligand, which upon treatment with 1 equiv. of [Ru(Cl) 2 (DMSO) 4 ], [36] 12 ], based on molecular modeling studies, [38] include a 17.5 Å internal diameter void region and a 37.5 Å overall diameter of the terpyridine lattice. The G1 dendrimer [(2 12À )(Na þ ) 12 ] was prepared by hydrolysis of the corresponding 12-tert-butyl ester with formic acid and was previously reported [39] to possess a hydrodynamic diameter of 23.6 Å at basic pH, as determined by 2D diffusion ordered spectroscopy (DOSY) NMR experiments.…”

“…[2][3][4] Examples of ion-based materials include a molecular capsule [5] made by two oppositely charged calix [4] arenes, pseudorotaxanes [6] accessed by ion-pair templation, polyelectrolyte-amphiphile monolayers, [7][8][9] and ion-pair interactions between biomolecular recognition sites and their guests. [10][11][12] Although these non-covalent associations are usually weaker and reversible when compared to most covalent interactions, ionically driven attractions exhibiting multiple interactions per specie can result in very strong binding energies.…”