Synthesis, characterization, and photoinduced CO-release reactivity of a Pb(II) flavonolate complex: Comparisons to Group 12 analogs

Bismuth(III) Flavonolates: The Impact of Structural Diversity on Antibacterial Activity, Mammalian Cell Viability and Cellular Uptake

“…Given the difference in ion size of Bi III ,t heseb ond lengths correspond wellw ith analogous MÀOb onds in the 3hydroxyflavonolate complexes with Mn II (2.1274(16) )a nd Fe III (1.955(7) ), [31] and are shorter than the equivalent bond in the Pb II 3-hydroxyflavonolatec omplex (2.2270 (19) ). [32] The carbonyl oxygens of the flavonolate ligands in 1b also coordinate to the Bi III centre, having longerB i ÀO(=C) bond lengths in the range of 2.476(3)-2.704(2) .B oth of the anionic and coordinative BiÀOb ond lengths in 1b are consistentw ith the range of reported BiÀOb ond distances. [33] The formation of five-membered O,O-chelate rings by the flavonolate ligands coordinating to the Bi III centre is consistent with the structures of other metal-flavonolate complexes.…”

“…[24a, 25, 37] The hydroxylate BiÀOb ondl engths of 2.293(3) (Bi(1)ÀO(1)) and 2.252(3) (Bi(1)ÀO(3)) are longer than the analogous bonds in the tris-substituted flavonolate complex 6b (2.182(3)-2.207(3) ), and longer than the hydroxylate PbÀOb ond in the 3-hydroxyflavonolate Pb II complex. [32] The coordinating DMSO molecule makes as ignificantly longer interaction (2.618(3) )t ot he Bi III centre through the O(5) oxygen atom compared to the two coordinating BiÀO=Ci nteractions made by the carbonyl oxygens of the flavonolate ligands (2.556(3) and 2.536(3) ). Complexes 1c, 2c,a nd 5c also crystallised with as ingle coordinatings olvent molecule (DMSOo rTHF) and show isostructural geometries to 6c•(DMSO).…”

“…[30a, 31-32] The three flavonolate O-Bi-O bite angles in 1b are in the range of 66.49(8)-69.33(8)8 which is similart ot he Pb II 3-hydroxyflavonolate complex( 68.14(7)8)p reviously described. [32] The carbonyl C=Od istances of the 3-hydroxyflavonolate ligandsi n1b are in the range of 1.254(4)-1.262 (4) which are elongated compared to free 3-hydroxyflavone (1.232(3) ). [34] However,t he hydroxylate CÀOb ond lengths (1.327(4)-1.336(4) )a re shorter compared to the free flavonol (1.357(3) ).…”

Theoretical study on the photooxygenation and photorearrangement reactions of 3-hydroxyflavone

“…20 The oxygenation of 3HF was also studied with the use of photosensitizers, and the same products (SA + CO) were obtained. 21 The photooxygenation of some metal complexes with (anionic) 3HF ligand also yields SA, releasing CO. [22][23][24] The direct as well as the photosensitized oxygenation of avonols, the natural 3HF derivatives, lead to the respective SA-s. 25,26 In deaerated solutions, a photorearrangement takes place resulting in 3-hydroxy-3-phenyl-indan-1,2-dione (IN). 27 These reactions are of importance in the characterization of the photostability of 3HF-based uorescent probes.…”

A bipyridine-ligated zinc(II) complex with bridging flavonolate ligation: synthesis, characterization, and visible-light-induced CO release reactivity

“…Examples include compounds that exhibit anticancer (M = Ru II ; Kurzwernhart et al, 2013;Saraf et al, 2014), antidiabetic (M = Zn II ; Vijayaraghavan et al, 2012), and antioxidant (Pieniazek et al, 2014;de Souza & de Giovani, 2004) properties. Radiopharmaceuticals (M = Re I ; Schutte et al, 2011) and light-induced CO releasing molecules (M = Zn II ; Grubel et al, 2011Grubel et al, , 2013 have also been developed based on metal-flavonolate structures. The 3-hydroxyflavonolate ligand typically coordinates in a bidentate Recently, we reported the first example of bridging flavonolate ligation in a dinuclear zinc complex using an extended flavonol ligand (Popova et al, 2017).…”