112881-51-3Relevant articles and documents
A facile route to sterically hindered and non-hindered 4′-aryl-2, 2′:6′,2″-terpyridines
Wang, Jianhua,Hanan, Garry S.
, p. 1251 - 1254 (2005)
A facile one-pot synthesis of 4′-aryl-2,2′:6′,2″- terpyridines from aryl aldehydes and 2-acetylpyridine is presented. The synthesis of terpyridines incorporating sterically hindered aryl groups, such as the 9-anthryl group, can also be readily synthesized using this method.
A study of binding interactions between terpyridine derivatives and cucurbit[10]uril
Deng, Yuanyuan,Yin, Hang,Zhao, Zhiyong,Wang, Ruibing,Liu, Simin
, p. 706 - 712 (2018)
The binding interactions of a series of 2,2′:6′,2″-terpyridine (TPY) derivatives and their metal complexes with cucurbit[10]uril (CB[10]) were investigated by 1H NMR, UV/Vis, emission spectroscopy, and ESI mass spectrometry. 1H NMR titrations revealed CB[10] could encapsulate methylated TPY (MTPY), and the binding ratio between guest MTPY and host was 1:1 and 2:1 via ESI-MS characterization. For the transition metal complexes composed of Fe(II) or Ru(II) or Rh(III) and TPY derivatives, the octahedral TPY?metal?TPY core can be included in the cavity of CB[10]. Three binding modes (1:1, 1:2 and 1:3) have been detected for the binding of the metal?MPTY complexes with CB[10] by ESI-MS.
Targeting G-quadruplex structures with Zn(ii) terpyridine derivatives: a SAR study
Biver, Tarita,Busto, Natalia,Carrión, M. Carmen,Díaz de Gre?u, Borja,García, Bego?a,Jalón, Felix A.,Manzano, Blanca R.,Montanaro, Sonia
, p. 13372 - 13385 (2020)
Based on the ability of terpyridines to react with G-quadruplex DNA (G4) structures along with the interest aroused by Zn as an essential metal centre in many biological processes, we have synthesized and characterized six Zn chloride or nitrate complexes containing terpyridine ligands with different 4′-substituents. In addition, we have studied their interaction with G4 and their cytotoxicity. Our experimental results revealed that the leaving group exerts a strong influence on the cytotoxicity, since the complexes bearing chloride were more cytotoxic than their nitrate analogues and an effect of the terpyridine ligand was also observed. The thermal stabilization profiles showed that the greatest stabilization of hybrid G4, Tel22, was observed for the Zn complexes bearing the terpyridine ligand that contained one or two methylated 4-(imidazol-1-yl)phenyl substituents,3Cland3(L)2, respectively, probably due to their extra positive charge. Stability and aquation studies for these complexes were carried out and no ligand release was detected. Complexes3Cland3(L)2were successfully internalized by SW480 cells and they seemed to be localized mainly in the nucleolus. The highest cytotoxicity, G4 selectivity and G4 affinity determined by fluorescence and ITC experiments, and subcellular localization quantified by ICP-MS measurements, rendered3Cla very interesting complex from a biological standpoint.
Ionic-liquid salt-mediated synthesis of 4′-(pyridyl)-terpyridines
Jadhav, Sumit V.,Ingole, Pravin G.,Bajaj, Hari C.
, p. 1142 - 1148 (2010)
One-pot reactions to produce isomeric 4′-(pyridyl) 2,2′:6′,2"-terpyridine under moderate conditions are described using imidazolium-based ionic liquid and quaternary ammonium-based molten salts as solvent media. The use of eutectic molten salts as a reaction media proved effective in sequential aldol and Michael addition reactions, leading to substituted terpyridines. The desired product was obtained in reasonable yield via a simple, one-pot reaction.
Syntheses, structures, and luminescence properties of lanthanide coordination polymers with a polycarboxylic terpyridyl derivative ligand
Xie, Juan,Shu, Hui-Ming,Hu, Huai-Ming,Han, Zhong-Xi,Shen, Sa-Sa,Yuan, Fei,Yang, Meng-Lin,Dong, Fa-Xin,Xue, Gang-Lin
, p. 985 - 994 (2014)
Solvothermal reactions of lanthanide chloride with a new ligand, H 3L, 4 ′-(3-carboxylpyridyl)-2,2 ′:6 ′,2"- terpyridine-6,6"-dicarboxylic acid, yields seven new lanthanide-organic frameworks: {[Ln2L2]'H2O}n (Ln=Pr (1), Nd (2), Sm (3), Eu (4)), {[Ln5L4(COO) 3(H2O)4]'10 H2O}n (Ln=Tb (5), Dy (6)), and [Yb2L2(H2O)2]'2 H2O (7). Single-crystal X-ray diffraction reveals that these complexes belong to three structural types. Type I (1-4) consists of lanthanide-carboxyl group layers pillared by L3- to form a three-dimensional network. Type II (5 and 6) comprises a right-handed helical chain and a left-handed helical chain linked through L3- anions into a three-dimensional framework. Type III (7) is a discrete dinuclear structure. The structural change is due to the decrease in the metal coordination number from nine for the large ions to seven for the small ions; this demonstrates the effect of lanthanide contraction. These materials exhibit high thermal stability. In addition, the luminescent properties of these complexes are discussed.
Case Study of the Correlation between Metallogelation Ability and Crystal Packing
Khavasi, Hamid Reza,Esmaeili, Maryam
, p. 4369 - 4377 (2019)
In the present paper, in order to find the correlation between the molecular structure and the intermolecular interaction patterns in the crystalline state and the corresponding gelating or nongelating behavior, two structurally related sets of copper complexes, including (CuCl2[LTerpy2py]), 1, (CuCl2[LTerpy3py]), 2, and (CuCl2[LTerpy4py]), 3, (where LTerpynpy is 4′-(n-pyridyl)-2,2′,6′,2″-terpyridine) as the first set and (CuCl2[Ldipyz-py2py]), 4, (CuCl2[Ldipyz-py3py]), 5, and (CuCl2[Ldipyz-py4py]), 6, (where Ldipyz-pynpy is 4-(n-pyridyl)-2,6-dipyrazin-2-yl-pyridine) as the second one, have been synthesized, and their crystal packing as well as gelating properties have been investigated. Results show that although these two sets are structurally similar the first set forms a metastable hydrogel, while the second one is unable to form a gel. To investigate the reasons, we employed Hirshfeld surface analysis and examined the differences in their packing arrangements, which suggest hydrogen bonding arranged into the three-dimensional network is a preferred mode of packing for the crystalline solid but is unfavorable for gel formation.
Molecular Assemblies and Spin-Crossover Behaviour of Cobalt(II) Complexes with Terpyridine Incorporating Different Nitrogen Positions in Pyridine Rings
Nakahara, Risa,Nakaya, Manabu,Shin, Jong Won,Ohtani, Ryo,Nakamura, Masaaki,Hayami, Shinya
, p. 494 - 498 (2017)
Cobalt(ii) complexes with terpyridine-type ligands, [Co(n-pyterpy)2](ClO4)2 (n=3 (1), 4 (2)), were prepared and characterised. Different positions of the nitrogen atom in the terpyridine ligands influenced their assembly properties in the crystal structures. Complex 1 showed a 2D network structure consisting of 1D chains connected by intermolecular NHC interactions. On the other hand, complex 2 consisted of two different cobalt ion sites (Co1 and Co2) with slightly different coordination environments. Complex 2 showed 1D chains with no interchain interactions. Such differences are discussed with the cooperativities estimated by their spin crossover behaviours.
Design and synthesis of mixed valent coordination networks containing pyridine appended terpyridyl, halide, and dicarboxylates
Banerjee, Kaustuv,Biradha, Kumar
, p. 4264 - 4274 (2012)
The ability of 4′-(4-pyridyl)-2,2′:6′,2′- terpyridine (L), which contains a chelating center as well as an exodentate center for coordination, to form mixed-valent coordination polymers together with bromide and organic dicarboxylates as bridges has been explored with Cu(I), Cu(II), Co(II), and Ni(II) metal salts using hydrothermal reactions. The mixed-valent complexes containing Cu(I) and Cu(II) with L were formed only when the organic anions are glutarate (GA) or 1,3-dicarboxylate (BDC). The glutarate-containing complex exhibits a double helix in which the opposite handed helices interact with each other via π-π interactions between the two L-units. In the case of the BDC-containing complex, the Br- joins the two Cu(I) and Cu(II) centers to form a one-dimensional (1D) network containing Cu2L2Br2 boxes. The HBDC units, which are connected to the above-mentioned 1D network, extend the dimensionality of the network to a three-dimensional (3D) network through catemeric -COOH interactions. The presence of succinate (SA) or biphenyl 2,6,2′,6′- tetracraboxylate (TCA) produced the complexes containing only Cu(II) but not Cu(I). The SA acts as a bridge between two Cu(II) centers to form one-dimensional chains containing Cu2L2SA2 boxes. On the other hand, the presence of TCA resulted in the formation of a 1D chain of CuL without TCA inclusion in the crystal lattice. The reactions of L in the presence of BDC with Ni(II) and Co(II) resulted in the formation of similar 1D isomeric chains containing ML units. All the six complexes were characterized by single crystal X-ray diffraction, IR, and diffuse reflectance spectroscopy studies. The mixed valence complexes were characterized by cyclic voltammetry.
Ligand Reactivity in Iron(II) Complexes of 4'-(4'''-Pyridyl)-2,2':6',2''-terpyridine
Constable, Edwin C.,Thompson, Alexander M. W. Cargill
, p. 2947 - 2950 (1992)
The ligand 4'-(4'''-pyridyl)-2,2':6',2''-terpyridine (pyterpy) acts as a tridentate ligand in which the 4-pyridyl ring is not co-ordinated in the complex cation 2+; the non-co-ordinated ring reacts with electrophiles to give species in which the charge perturbations are localised to a '4,4'-bipyridyl' fragment.
Vectorial property dependence in bis{4′-(n-pyridyl)-2,2′: 6′,2″-terpyridine}iron(ii) and ruthenium(ii) complexes with n = 2, 3 and 4
Beves, Jonathon E.,Dunphy, Emma L.,Constable, Edwin C.,Housecroft, Catherine E.,Kepert, Cameron J.,Neuburger, Markus,Price, David J.,Schaffner, Silvia
, p. 386 - 396 (2008)
A comparative structural and spectroscopic investigation of the complexes [M(1)2]2+, [M(2)2]2+ and [M(3) 2]2+ in which M = Fe or Ru, and ligands 1, 2 and 3 are 4′-(2-pyridyl)-, 4′-(3-pyridyl)- and 4′-(4-pyridyl)-2, 2′:6′,2″-terpyridine, respectively, is reported. The complexes [Ru(1)2]2+, [Ru(2)2]2+ and [Ru(3)2]2+ undergo mono- and bis-N-methylation. The consequences of methylation on the absorption spectra and electrochemical properties are discussed; the solid-state structure of the bis(N-methylated) derivative of [Ru(2)2][PF6]2 is presented. This journal is The Royal Society of Chemistry.
