Ligands containing the btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] motif have appeared with increasing regularity over the last decade. This class of ligands, formed in a one pot ‘click’ reaction, has been studied for various purposes, such as for generating d and f metal coordination complexes and supramolecular self-assemblies, and in the formation of dendritic and polymeric networks, etc. This review article introduces btp as a novel and highly versatile terdentate building block with huge potential in inorganic supramolecular chemistry. We will focus on the coordination chemistry of btp ligands with a wide range of metals, and how it compares with other classical pyridyl and polypyridyl based ligands, and then present a selection of applications including use in catalysis, enzyme inhibition, photochemistry, molecular logic and materials, e.g. polymers, dendrimers and gels. The photovoltaic potential of triazolium derivatives of btp and its interactions with anions will also be discussed.

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The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: A new versatile terdentate ligand for supramolecular and coordination chemistry

Seven diiron(II) complexes, [Fe(II)(2)(PMAT)(2)](X)(4), varying only in the anion X, have been prepared, where PMAT is 4-amino-3,5-bis{[(2-pyridylmethyl)-amino]methyl}-4H-1,2,4-triazole and X = BF(4)(-) (1), Cl(-) (2), PF(6)(-) (3), SbF(6)(-) (4), CF(3)SO(3)(-) (5), B(PhF)(4)(-) (6), and C(16)H(33)SO(3)(-) (7). Most were isolated as solvates, and the microcrystalline ([3], [4]·2H(2)O, [5]·H(2)O, and [6]·½MeCN) or powder ([2]·4H(2)O, and [7]·2H(2)O) samples obtained were studied by variable-temperature magnetic susceptibility and Mossbauer methods. A structure determination on a crystal of [2]·2MeOH·H(2)O, revealed it to be a [LS-HS] mixed low spin (LS)-high spin (HS) state dinuclear complex at 90 K, but fully high spin, [HS-HS], at 293 K. In contrast, structures of both [5]·¾IPA·H(2)O and [7]·1.6MeOH·0.4H(2)O showed them to be [HS-HS] at 90 K, whereas magnetic and Mossbauer studies on [5]·H(2)O and [7]·2H(2)O revealed a different spin state, [LS-HS], at 90 K, presumably because of the difference in solvation. None of these complexes undergo thermal spin crossover (SCO) to the fully LS form, [LS-LS]. The PF(6)(-) and SbF(6)(-) complexes, 3 and [4]·2H(2)O, appear to be a mixture of [HS-LS] and [HS-HS] at low temperature, and undergo gradual SCO to [HS-HS] on warming. The CF(3)SO(3)(-) complex [5]·H(2)O undergoes gradual, partial SCO from [HS-LS] to a mixture of [HS-LS] and [HS-HS] at T(1/2) ≈ 180 K. The B(PhF)(4)(-) and C(16)H(33)SO(3)(-) complexes, [6]·(1)/(2)MeCN and [7]·2H(2)O, are approximately [LS-HS] at all temperatures, with an onset of gradual SCO with T(1/2) > 300 K.

Effect of Counteranion X on the Spin Crossover Properties of a Family of Diiron(II) Triazole Complexes [FeII2(PMAT)2](X)4

Spin-Crossover in Discrete Polynuclear Complexes

The polydentate ligand 2,6-bis(5-(2-hydroxyphenyl)-pyrazol-3-yl)-pyridine, H4L, exhibits a series of coordination pockets favoring the establishment of metal sequences with predetermined motifs, together with a degree of flexibility for the formation of clusters with various overall topologies With Cu(II) under strong basic conditions it has a marked tendency to stabilize a cyclic [Cu16L8] cluster The sequential formation of this compound via [Cu7L8]2– intermediates, recognized in its structure, is suggested by crystallographic evidence, which shows the persistent formation of the complex salt (NBu4)2[Cu7L8] in the presence of the organic cation Also, the crystallographic identification of the related cluster [Cu11L5(OH)2(py)12] from similar reaction conditions underscores the rich multiplicity of species attainable from this simple reaction system

Linear or cyclic clusters of Cu(II) with a hierarchical relationship.

The synthesis of a novel cyclophane (L1) consisting of a 1H-pyrazole moiety linked through methylene groups to a 1,5,9,13-tetraazadecane chain is described. As far as we know, this is one of the first reported syntheses of a [1 + 1] condensation 1H-pyrazole azamacrocyclic ligand. The crystal structures of the complexes [Cu2(H(H–1L1))(H–1L1)](ClO4)3·3.75H2O (1) and ([Cu2(H(H–1L1))0.5(H–1L1)1.5]2(ClO4)3Br2·4.2H2O (2) show that Cu2+ coordination leads to formation of 2:2 Cu2+:L dinuclear dimeric complexes in which the 1H-pyrazole units lose a proton behaving as bis(monodentate) bridging ligands. Unlike previously reported complexes of [2 + 2] pyrazole azamacrocycles, the pyrazolate units in 1 are pointing outward from the macrocyclic cavity to bind the Cu2+ ions. Inner coordination with formation of 1:1 Cu2+:L complexes is however observed in [1 + 1] pyridine azamacrocycles as shown by the crystal structure here presented of the complex [CuL2](ClO4)2 (3). Crystals of [Cu3(H–1L1)2(CO3)(H2O)](ClO4)2·8H2O (4) g...

Intermolecular Binding Modes in a Novel [1 + 1] Condensation 1H-Pyrazole Azamacrocycle: A Solution and Solid State Study with Evidence for CO2 Fixation

The bis-terdentate pyrazole-based ligand 3,5-bis{[N-(2-pyridylmethyl)amino]methyl}-1H-pyrazole (PMAPH) was synthesized from 3,5-(1H)-pyrazoledicarbaldehyde and 2 equiv of 2-(aminomethyl)pyridine, using sodium borohydride to reduce the imine intermediate. A family of dinuclear complexes [MII/III2(PMAP)2](X)2/4 was prepared by 2:2:2 reactions of MX2/PMAPH/base, where M = ZnII and X = BF4 -; M =CuII and X = ClO4-, BF4-, OAc-, NO3-; M =NiII, FeIII and X = ClO4-, BF4-; M = FeII and X = SbF6-. Single crystal X-ray structure determinations on four complexes: [FeIII 2(PMAP)2]-(BF4)4 3 2MeCN, [NiII2(PMAP)2](ClO4)2 3 2MeCN, [CuII2(PMAP)2](BF4)2 3 2MeCN, and [ZnII2(PMAP)2](BF4)2 3 2MeCN confirmed a dinuclear doubly pyrazolate-bridged structure for each. The two metal centers in these complexes have similar N6 distorted octahedral coordination spheres, with all donors provided by the two deprotonated PMAP- ligands. Magnetic measurements reveal intra-dinuclear antiferromagnetic interactions for both the M = CuII and NiII [M2(PMAP)2](BF4)4 complexes, with J/kB = -252(2) K and J/kB = -24.7(2) K (H = -2JSMSM), respectively. Interestingly magnetic measurements show that the complex [Fe2 II(PMAP)2](SbF6)2 3 2.25(C3H8O) is in a mixed high spin (HS)-low spin (LS) spin state, [HS-LS], from 300 to 1.8 K, with no sign of spin crossover to a fully low spin form [LS-LS] even at 1.8 K.

Doubly Pyrazolate-Bridged Dinuclear Complexes of a Highly Constrained Bis-terdentate Ligand: Observation of a [High Spin-Low Spin] State for [FeII2(PMAP)2][SbF6]2·2.25(C3H8O) (PMAP = 3,5-bis{[N-(2-pyridylmethyl)amino]-methyl}-1H-pyrazolate)

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Doubly Pyrazolate-Bridged Dinuclear Complexes of a Highly Constrained Bis-terdentate Ligand: Observation of a [High Spin-Low Spin] State for [FeII2(PMAP)2][SbF6]2·2.25(C3H8O) (PMAP = 3,5-bis{[N-(2-pyridylmethyl)amino]-methyl}-1H-pyrazolate)