Terrylenimides: New NIR Fluorescent Dyes

F O Holtrup; G R J Müller; H Quante; S De Feyter; F C De Schryver; K Müllen

doi:10.1002/chem.19970030209

Terrylenimides: New NIR Fluorescent Dyes

Chemistry. 1997 Feb;3(2):219-25. doi: 10.1002/chem.19970030209.

Authors

F O Holtrup¹, G R J Müller, H Quante, S De Feyter, F C De Schryver, K Müllen

Affiliation

¹ Max-Planck-Institut für Polymerforschung Ackermannweg 10, 55128 Mainz (Germany), Fax: Int. code +(6131)379-350.

PMID: 24022951
DOI: 10.1002/chem.19970030209

Abstract

Terrylenimides 3 and 4 represent a new class of blue colorants, exhibiting absorption maxima at 650 to 700 nm and fluorescence emissions in the NIR region (673 to 750 nm). The terrylenimides were synthesized by means of various organometallic coupling reactions, catalyzed by transition metal complexes (Ni(o) , Pd(o) ) and starting from the aromatic bromides, boronic acids, or organotin compounds. The terrylenimides have all the properties expected of excellent fluorescent dyes: high extinction coefficients, high fluorescence quantum yields, and very good thermal, chemical, and photochemical stabilities. Owing to its extended π system, 3 can reversibly accept four negative charges. By varying the substituents, 3 and 4 can be modified to serve either as soluble dyes or as insoluble pigments.

Keywords: C-C coupling; arenes; dyes; fluorescence; terrylenes.