A versatile standard for bathochromic fluorescence based on intramolecular FRET

Abstract

A perylene and a terrylene tetracarboxylic bisimide dyad was prepared in which an efficient energy transfer from the former to the latter is observed. The absorption spectrum of this compound covers a broad range. Bathochromic fluorescence with a high quantum yield was obtained independent of excitation wavelengths (l o 655 nm). The dyad can be recommended for the use of calibrating fluorescence spectrometers, as well as a fluorescence standard in the bathochromic region.

Electronic Modulation of Terrylene Diimides Leading to Core‐Twisting, Tunable Emission and Intermolecular Interactions

“…The fluorescence quantum yields obtained were 16 and 22 % for TDI-Ph and TDI-PhCN, respectively with respect to parent TDI (Φ = 90 %) as reference. [7,8] The emission from TDI-PhNMe 2 was quenched, further supporting the CT transition from dimethylaminophenyl group to the TDI core. The fluorescence data has been given in Table 1.…”

“…The broadening of emission bands may be attributed to the twisting in the aromatic terrylene core. The fluorescence quantum yields obtained were 16 and 22 % for TDI‐Ph and TDI‐PhCN , respectively with respect to parent TDI (Φ = 90 %) as reference , . The emission from TDI‐PhNMe 2 was quenched, further supporting the CT transition from dimethylaminophenyl group to the TDI core.…”

“…[2] Among larger RDIs, terrylene diimides (TDIs) have transpired as important dyes for single molecule spectroscopy studies, membrane labeling and enzyme tracking experiments because of their inherent higher absorption coefficients in the NIR region with high fluorescence quantum yields. [3][4][5][6][7][8] TDIs also exhibit high thermal and photochemical stabilities, which makes them compatible for use in organic field-effect transistors, photochromic switches, supramolecular self-assemblies, and organic solar cell applications. [9][10][11][12][13][14][15][16] The extended π-conjugation of TDIs show efficient charge transport properties.…”

High Performance Recycling of Polymers by Means of Their Fluorescence Lifetimes*

“…The fluorescence labels 1 (PTIE) [15], 2 (S-13) [16], and 3 (S-13TBI) [17] [18] were prepared according to the literature. Spectroscopic grade solvents were applied.…”

Functional Organo-Nano Particles by RAFT Copolymerisation

“…For covering the even more bathochromic spectral region terrylenebiscarboximides were applied meaning a naphthalene-core-prolonged perylenebiscarboximide. Synthesis started similarly to 4a/b with a terrylene biscarboximide [18] with two even more effectively solubilising 1-nonyldecyl substituents, hydrolysing to give the corresponding anhydridecarboximide and its condensation with 4-aminostyrene to obtain 5. For the more hypsochromic spectral region perylenebiscarboximide with two solubilising 1-hexylheptyl substituents was core-modified by means of a Diels-Alder-Clar reaction with maleic anhydride leading in a five-membered ring anhydride [25] that was condensed with 4-aminostyrene to obtain the benzoperylene-derived label 6.…”