Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Abstract

The dipyrrin–metal complexes and especially the boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have recently attracted considerable attention because of their interesting properties and possible applications. We have developed two unique and useful ways to extend versatility and usefulness of the dipyrrin complexes. The first one is the linear and macrocyclic oligomerization of the BODIPY units. These arrangements of the B–F moieties of the oligomerized BODIPY units provide sophisticated functions, such as unique recognition ability toward cationic guest, associated with changes in the photophysical properties by utilizing unprecedented interactions between the B–F and a cationic species. The second one is introduction of additional ligating moieties into the dipyrrin skeleton. The multidentate N₂O_x dipyrrin ligands thus obtained form a variety of complexes with 13 and 14 group elements, which are difficult to synthesize using the original N₂ dipyrrin derivatives. Interestingly, these unique complexes exhibit novel structures, properties, and functions such as guest recognition, stimuli-responsive structural conversion, switching of the optical properties, excellent stability of the neutral radicals, etc. We believe that these multifunctional dipyrrin complexes will advance the basic chemistry of the dipyrrin complexes and develop their applications in the materials and medicinal chemistry fields.

1 Introduction

2 Linear Oligomers of Boron–Dipyrrin Complexes

3 Cyclic Oligomers of Boron–Dipyrrin Complexes

4 A Cyclic Oligomer of Zinc–Dipyrrin Complexes

5 Group 13 Element Complexes of N₂O_x Dipyrrins

6 Chiral N₂ and N₂O_x Dipyrrin Complexes

7 Group 14 Element Complexes of N₂O₂ Dipyrrins

8 Other N₂O₂ Dipyrrin Complexes with Unique Properties and Functions

9 Conclusion

Key words

dipyrrin - BODIPY - guest recognition - fluorescence - oligomer - multidentate ligand - complex of 13 and 14 group elements

• References and Notes

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