Synthesis and Characterization of Fluorescent Pyrrolyldipyrrinato Sn(IV) Complexes

Abstract

A series of neutral, 5-coordinate pyrrolyldipyrrinato Sn(IV) complexes have been synthesized via reaction of a pyrrolyldipyrrin, or its corresponding hydrochloride salt, with dibutyltin or diphenyltin oxide. The complexes are structurally unique in that all three nitrogen atoms of the pyrrolyldipyrrinato ligand bind to the tin center, making these complexes the first examples of pyrrolyldipyrrins behaving as LX(2) ligands. The complexes are highly fluorescent, exhibiting fluorescence quantum yields between 0.28 and 0.61, and display interesting preliminary biological activity.

New luminophors based on the binuclear helicates of d-METALS with BIS(DIPYRRIN)S

“…At the present time two main areas of influence on the fluorescence of dipyrrin luminophors are developed. The first using a new type of ligands with higher rigidity of molecules (N 2 O 2 -type [17][18][19][20][21] and N 3 -type [22]), and the second varies the nature of the complexing agent (d-and f-metals, [13,15,16,23] Ga(III) and…”

Symmetry-Breaking Charge Transfer of Visible Light Absorbing Systems: Zinc Dipyrrins

“…39,40 However, in spite of the increasing number of reported metallodipyrrins, 37,41−51 their photophysics are not well-understood. Unlike the highly fluorescent bDIPs, 36,37 homoleptic complexes MD n (D = dipyrrin or π-extended dipyrrin ligands) 43,44,46,47,49 generally exhibit low to moderate fluorescent quantum yields.…”

“…In contrast, the heteroleptic complexes MDX n (X is an ancillary ligand) were shown to have quite high luminescent efficiencies (up to 80%). 41−45,50,51 …”

Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II)

“…Furthermore, chelation facilitates the coordination of pyrrolyldipyrrinato ligands to tin(IV) complexes that feature a pyrrolide and a dipyrrinato unit. 21 Coordination of pyridylpyrrolides to K, Cu, Ag, Au and Rh has recently been reported. 22 Bidentate coordination of pyrrole to ruthenium has also been accomplished through the reaction of TpRu(CO)(NCMe)(Me) with pyrrole, which results in the formation of product B.…”