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Synthesis and Modification of Terrylenediimides as High‐Performance Fluorescent Dyes
Author(s) -
Nolde Fabian,
Qu Jianqiang,
Kohl Christopher,
Pschirer Neil G.,
Reuther Erik,
Müllen Klaus
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200401177
Subject(s) - solubility , fluorescence , imide , combinatorial chemistry , chemistry , absorption (acoustics) , water soluble , molecule , organic chemistry , materials science , physics , quantum mechanics , composite material
Two new synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross‐coupling reaction followed by a cyclodehydrogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled with a variety of compounds, for example, by Suzuki cross‐coupling, which can lead to an array of terrylenediimides with new functional groups such as hydroxy, amino, or carboxy groups needed to link up with other molecules. The functionalisation in the bay region is used to tune the properties of terrylenediimides and extend the range of applications, for example, by introducing water solubility. These tetrasubstituted terrylenediimides offer, depending on the substituents used, exciting features such as good solubility in common organic solvents, water solubility, or NIR absorption.