Coordination-Driven Self Assembly of a Brilliantly Fluorescent Rhomboid Cavitand Composed of Bodipy-Dye Subunits

Abstract

The two sp(3) hybridized fluorine atoms of a Bodipy dye have been synthetically replaced with the linear donor ligand 4-ethynylpyridine (-C≡C-Py) to form a rigid and highly symmetrical 109.5° building block in which the fluorophore subunit is vertically aligned to the plane formed by the -C≡C-Py donors. Upon reaction of the above tecton with a 90° organoplatinum acceptor unit, an intensely fluorescent rhomboid cavitand was manifested in solution. In contrast to the vast majority of coordination-driven self-assembled chromophoric systems, the present one fully conserves the excellent photophysical properties of the parent Bodipy dye. These unique features of the present metallosupramolecular entity constitute a fascinating metal-to-ligand self-assembled prototype for building compact and intensely luminescent materials with host-guest capabilities.

Recent Developments of Supramolecular Metal-based Structures for Applications in Cancer Therapy and Imaging

“…Noteworthy, in this area, Borondipyrromethene (BODIPY) is a class of fluorescent dyes used for many applications such as light harvesting, imaging, in solar cells and for PDT 99-101. Thus, BODIPY-based palladium, platinum, iron, and zinc supramolecular structures have been synthesized by self-assembly and analysed for their host-guest chemistry and biological properties 102-104. Inspired by these properties of BODIPY-based supramolecules, Gupta, Lee and coworkers designed, synthesized, and studied for their antiproliferative activities new ruthenium and iridium metalla-rectangles featuring a BODIPY-based linker (Figure 5) 103, 105.…”

Self-Assembly of Bodipy-Derived Extended π-Systems

“…103106 The coordination-driven self-assembly of Bodipy dyes (49, 5255) and platinum complexes (50 and 51) has been studied in rhomboid type cavitand (Figure 19). 107,108 The Bodipy derivative (49) was prepared by replacing the tetrahedral fluorine atoms present in the Bodipy core with ethynyl pyridine linker. The Bodipy moiety was vertically aligned to the plane of the ethynyl pyridine units.…”

Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction

“…500 nm), narrow emission bands and high emission intensity. They have been used as laser dyes [9][10][11][12][13][14][15][16][17][18][19][20], markers [21,22], sensors [23][24][25][26][27][28] in modern chemistry and biology [29]. It is well known that the functionalities on 3-, 4-, 5-and 8-positions of the BODIPY core (Figure 1) strongly impact its optical properties [30][31][32][33], which led to many efforts to design BODIPY-based sensor molecules [34][35][36][37][38][39].…”