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Journal articles on the topic 'Substituted terpyridine'

Author: Grafiati

Published: 4 June 2025

Last updated: 23 June 2025

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1

Krinochkin, Alexey P., Dmitry S. Kopchuk, Albert F. Khasanov, et al. "Unsymmetrically functionalized 5,5″-diaryl- and 5,6,5″-triaryl-2,2′:6′,2″-terpyridines: an efficient synthetic route and photophysical properties." Canadian Journal of Chemistry 95, no. 8 (2017): 851–57. http://dx.doi.org/10.1139/cjc-2017-0195.

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An efficient approach for the synthesis of 5,5″- or 5,6,5″-aryl substituted 2,2′:6′,2″-terpyridines, bearing an anneleted cyclopentene unit in one of the side-chain pyridine rings for the improved solubility in organic solvents, via their 1,2,4-triazine analogues has been developed. By using this approach, various aromatic substituents were introduced in the 2,2′:6′,2″-terpyridine core. Depending on the nature of the aromatic substituents, the obtained terpyridines exhibited an intense emission in a range of ca. 344–394 nm in acetonitrile solutions. For the most representative compounds, pronounced bathochromic shifts in both absorption and emission spectra were observed compared with previously reported substituted terpyridines.

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2

Ion, Adrian E., Liliana Cristian, Mariana Voicescu, et al. "Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines." Beilstein Journal of Organic Chemistry 12 (August 11, 2016): 1812–25. http://dx.doi.org/10.3762/bjoc.12.171.

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4′-Azulenyl-substituted terpyridines were efficiently synthesized following the Kröhnke methodology via azulenylchalcone intermediates. These azulenyl-containing terpyridines showed fluorescent emission with a fluorescence quantum yield varying from 0.14, in the case of parent terpyridine, to 0.64 when methyl groups are grafted on the azulenyl seven-membered ring. According to the crystal structures and TDDFT calculations, different twisting of the aromatic constituents is responsible for the observed fluorescent behavior. The electrochemical profile contains one-electron oxidation/reduction steps, which can only be explained on the basis of the redox behavior of the azulene unit. The ability of the 4′-azulenyl 2,2′:6′,2″-terpyridine to bind poisoning metal cations was studied by UV–vis titrations using aqueous solutions of Hg(II) and Cd(II) chlorides as illustrative examples.

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3

Klein, Y., Alessandro Prescimone, Mariia Karpacheva, Edwin Constable, and Catherine Housecroft. "Substituent Effects in the Crystal Packing of Derivatives of 4′-Phenyl-2,2′:6′,2″-Terpyridine." Crystals 9, no. 2 (2019): 110. http://dx.doi.org/10.3390/cryst9020110.

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We report the preparation of a series of new 4′-substituted 2,2′:6′,2″-terpyridines: 4′-(3,5-dimethylphenyl)-2,2′:6′,2″-terpyridine (2), 4′-(3-fluoro-5-methylphenyl)-2,2′:6′,2″-terpyridine (3), 4′-(3,5-difluorophenyl)-2,2′:6′,2″-terpyridine (4), and 4′-(3,5- bis(trifluoromethyl)phenyl)-2,2′:6′,2″-terpyridine (5). The compounds have been characterized by mass spectrometry, solid-state IR spectroscopy and solution NMR and absorption spectroscopies. The single-crystal X-ray diffraction structures of 3, 5 and 6·EtOH (6 = 4′-(3,5-bis(tert-butyl)phenyl)-2,2′:6′,2″-terpyridine) have been elucidated. The molecular structures of the compounds are unexceptional. Since 3 and 5 crystallize without lattice solvent, we are able to understand the influence of introducing substituents in the 4′-phenyl ring and compare the packing in the structures with that of the previously reported 4′-phenyl-2,2′:6′,2″-terpyridine (1). On going from 1 to 3, face-to-face π-stacking of pairs of 3-fluoro-5-methylphenyl rings contributes to a change in packing from a herringbone assembly in 1 with no ring π-stacking to a layer-like packing. The latter arises through a combination of π-stacking of aromatic rings and N…H–C hydrogen bonding. On going from 3 to 5, N…H–C and F…H–C hydrogen-bonding is dominant, supplemented by π-stacking interactions between pairs of pyridine rings. A comparison of the packing of molecules of 6 with that in 1, 3 and 5 is difficult because of the incorporation of solvent in 6·EtOH.

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4

Husson, Jérôme, and Laurent Guyard. "4′-(5-N-Propylthiophen-2-yl)-2,2′:6′,2″-terpyridine." Molbank 2021, no. 1 (2021): M1183. http://dx.doi.org/10.3390/m1183.

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A new thiophene-substituted terpyridine derivative has been prepared through the reaction between 5-n-propylthiophene-2-carboxaldehyde and 2-acetylpyridine. This terpyridine derivative bears an alkyl chain linked via a thiophene heterocycle.

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5

Husson, Jérôme, and Laurent Guyard. "4′-(N-(Propan-1,2-dienyl)pyrrol-2-yl)-2,2′:6′,2″-terpyridine." Molbank 2020, no. 2 (2020): M1142. http://dx.doi.org/10.3390/m1142.

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A new pyrrole-substituted terpyridine derivative that possesses an allene moiety was obtained as an “unexpected” sole product during an attempt to alkylate the N-atom of pyrrole with propargyl bromide in order to obtain an alkyne-functionalized terpyridine.

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6

Batalini, Claudemir, and Wagner Ferraresi De Giovani. "Synthesis and characterization of a new ruthenium (II) terpyridyl diphosphine complex." Acta Scientiarum. Technology 45 (September 27, 2023): e62458. http://dx.doi.org/10.4025/actascitechnol.v45i1.62458.

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Ruthenium complexes have been prepared for several applications, mostly for electrocatalysis, catalytic hydrogenation, energy conversion, photolysis, medicinal chemistry, among other fields. Bipyridine and terpyridine ligands are commonly found in the metal coordination sphere, including ruthenium, largely due to the high stability exhibited by the resulting complex and the possibility of greater stereochemical control during synthesis. The combination of substituted terpyridine ligands with diphosphine ligands to the metal ruthenium occurs to a lesser extent and its catalytic potential has been examined in several studies. This paper describes the synthesis of a new ruthenium (II) aqua complex containing aryl diphosphine and substituted terpyridine ligands: [Ru(L)(totpy)(OH2)](ClO4)2 (L=Ph2PCH2CH2PPh2); (totpy=4´-(4-tolyl)-2,2´:6´,2´´-terpyridine). The synthesis route was conducted in three steps; the final and the intermediate products have shown good reaction yields; the results of the characterization of the aqua complex by cyclic voltammetry, UV-visible spectroscopy and elemental analysis are consistent with the proposed chemical structure.

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7

Liang, Xing, Jinzhang Jiang, Xingyong Xue, et al. "Synthesis, characterization, photoluminescence, anti-tumor activity, DFT calculations and molecular docking with proteins of zinc(ii) halogen substituted terpyridine compounds." Dalton Transactions 48, no. 28 (2019): 10488–504. http://dx.doi.org/10.1039/c8dt04924f.

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8

Beneto, Arockiam Jesin, Jae Yoon Jeong, and Jong S. Park. "Sub-phthalocyanine-incorporated Fe(ii) metallo-supramolecular polymer exhibiting blue-to-transmissive electrochromic transition with high transmittance and coloration efficiency." Dalton Transactions 47, no. 45 (2018): 16036–39. http://dx.doi.org/10.1039/c8dt03587c.

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9

Bakkar, Assil, Saioa Cobo, Frédéric Lafolet, Diego Roldan, Eric Saint-Aman, and Guy Royal. "A redox- and photo-responsive quadri-state switch based on dimethyldihydropyrene-appended cobalt complexes." Journal of Materials Chemistry C 4, no. 6 (2016): 1139–43. http://dx.doi.org/10.1039/c5tc04277a.

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A multi-addressable quadri-state molecular switch based on the redox and photochromic properties of a dimethyldihydropyrene-substituted terpyridine cobalt complex has been designed and fully characterized.

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10

Constable, Edwin C., Catherine E. Housecroft, Markéta Šmídková, and Jennifer A. Zampese. "Phosphonate-functionalized heteroleptic ruthenium(II) bis(2,2′:6′,2″-terpyridine) complexes." Canadian Journal of Chemistry 92, no. 8 (2014): 724–30. http://dx.doi.org/10.1139/cjc-2014-0065.

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The heteroleptic complexes [Ru(1)(4)][PF6]2, [Ru(2)(4)][PF6]2, [Ru(Phtpy)(4)][PF6]2, and [Ru(pytpy)(4)][PF6]2 (Phtpy = 4′-phenyl-2,2′:6′,2″-terpyridine, pytpy = 4′-(4-pyridyl)-2,2′:6′,2″-terpyridine, 1 and 2 = 4-methyl ester substituted derivatives of Phtpy and pytpy, 4 = ethyl 2,2′:6′,2″-terpyridine-4′-phosphonate) have been prepared. The single crystal structure of ligand 1 (1 = methyl 4-carboxy-4′-phenyl-2,2′:6′,2″-terpyridine) is reported. The introduction of the 4-methyl ester group causes a small red shift in the MLCT band of the ruthenium(II) complexes and a small shift to a more positive potential for the Ru2+/Ru3+ couple. The new complexes should serve as a useful starting point for development of ruthenium(II) dyes suited for sensitization of p-type semiconductors.

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11

Salimova, I. O., A. A. Moiseeva, N. V. Zyk, and E. K. Beloglazkina. "Synthesis of triethylene glycol-substituted phenylterpyridine with a terminal aurophilic group and its coordination compound with Rh(III) for adsorption on the gold surface." Журнал органической химии 59, no. 5 (2023): 616–24. http://dx.doi.org/10.31857/s0514749223050087.

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A method has been developed for the preparation of a conjugate of 4-substituted phenylterpyridine and lipoic acid with a triethylene glycol linker between the terpyridine and sulfur-containing fragments. A coordination compound of the obtained terpyridine with Rh(III) have been synthesized. The ability of the resulting ligand and rhodium complex to be chemisorbed on the surface of gold electrodes with the formation of an Au-S bond have been shown using the cyclic voltammetry.

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12

Husson, Jérôme, and Laurent Guyard. "4,4″-Dichloro-4′-(2-thienyl)-2,2′:6′,2″-terpyridine." Molbank 2019, no. 3 (2019): M1071. http://dx.doi.org/10.3390/m1071.

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A new thiophene-substituted terpyridine derivative has been prepared and characterized. This ligand features a thiophene heterocycle (as an electrochemically polymerizable unit) as well as two chlorine atoms for further functionalization.

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13

Li, Jiahe, Hao Yan, Zhiyuan Wang, et al. "Copper chloride complexes with substituted 4′-phenyl-terpyridine ligands: synthesis, characterization, antiproliferative activities and DNA interactions." Dalton Transactions 50, no. 23 (2021): 8243–57. http://dx.doi.org/10.1039/d0dt03989f.

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Eleven copper chloride complexes with substituted 4′-phenyl-terpyridine ligands: high antiproliferative activities against five human carcinoma cell lines, strong affinity for binding with DNA as intercalators and multiple molecular docking results.

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14

Shokouhi Mehr, Hamideh, Natalie C. Romano, Rashid Altamimi, Jody M. Modarelli, and David A. Modarelli. "Core substituted naphthalene diimide – metallo bisterpyridine supramolecular polymers: synthesis, photophysics and morphology." Dalton Transactions 44, no. 7 (2015): 3176–84. http://dx.doi.org/10.1039/c4dt02719a.

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A series of metallo Ru(ii), Fe(ii), Co(ii) bisterpyridine polymers were prepared with core-substituted naphthalene diimide (NDI) groups inserted between two 4′-phenyl-2,2:6′,2′′-terpyridine (phtpy) groups.

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15

Liu, Junmin, Markus Tonigold, Björn Bredenkötter, Tobias Schröder, Jochen Mattay, and Dirk Volkmer. "Synthesis of terpyridine-substituted calix[n]arenes." Tetrahedron Letters 50, no. 12 (2009): 1303–6. http://dx.doi.org/10.1016/j.tetlet.2009.01.044.

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16

Benniston, Andrew C., Louis J. Farrugia, Philip R. Mackie, Paul Mallinson, William Clegg, and Simon J. Teat. "Properties and single-crystal X-ray structure of Bis[3,3″-bis(4-methylphenyl)-2,2′:6′,2″-terpyridine]iron(II) hexafluorophosphate - acetonitrile - diisopropyl ether (1/1.5/1)." Australian Journal of Chemistry 53, no. 8 (2000): 707. http://dx.doi.org/10.1071/ch99167.

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Absorption and electrochemical properties are reported for the iron(II) complex of the unusually substituted ligand 3,3″-bis(4-methylphenyl)-2,2′:6′,2″-terpyridine, along with the structure determination of the complex by single-crystal X-ray crystallography. Crystal data for C67H64.5F12FeN7.5OP2, M 1336.6: triclinic, a 12.768(3), b 15.789(4), c 17.160(4) Å, α 85.553(6), β 77.756(6), γ 66.754(5)˚, V 3106.1(12) Å3, space group P 1, Z 2, ρ 1.43 g cm–3, µ 0.30 mm-1 for λ 0.6849 Å, R 0.091 for 4456 observed (I > 2σ(I) ) reflections, wR2 0.241, Δρ1.68 e Å–3. The structural analysis reveals that, as observed in analogous bisterpyridineiron(II) complexes, the ligands adopt the preferred meridional binding motif. As a result, the ‘pulling-in’ of the outer pyridine rings forces each pair of 3,3″ substituted tolyl groups to diverge, resulting in an average distance between the tolyl methyl groups of c. 11.6 Å. The cyclic voltammetery of the complex in MeCN displays upon oxidative scanning a reversible one-electron wave (E˚ = + 0.99 V v. s.c.e.) and three one-electron waves under reducing conditions (E1˚ = –1.27 V, E2˚ = –1.51 V, E3˚ = –1.96 V v. s.c.e.). The electronic spectrum in acetonitrile contained an MLCT band centred at 571 nm, with a molar absorption coefficient of 18210 M–1 cm–1. When compared to similar phenyl-substituted terpyridine ligand iron(II) complexes this is a relatively low value and is assigned to reduced electronic delocalization throughout the terpyridine backbone.

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17

Granifo, Juan, Sebastián Suárez, and Ricardo Baggio. "The enrichment ratio of atomic contacts in the crystal structure of isomeric, triply protonated, 4′-functionalized terpyridine cations with [ZnCl4]2− as counter-ion." Acta Crystallographica Section E Crystallographic Communications 74, no. 12 (2018): 1881–86. http://dx.doi.org/10.1107/s2056989018016250.

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We report herein the synthesis, crystallographic analysis and a study of the non-covalent interactions observed in the new 4′-substituted terpyridine-based derivative bis[4′-(isoquinolin-2-ium-4-yl)-4,2′:6′,4′′-terpyridine-1,1′′-diium] tris-[tetrachloridozincate(II)], (C24H19N4)2[ZnCl4]3 or (44TPH3)2[ZnCl4]3, where (44TPH3)3+ is the triply protonated cation 4′-(isoquinolinium-4-yl)-4,2′:6′,4′′ terpyridinium. The compound is similar in its formulation to the recently reported 2,2′:6′,2′′ terpyridinium analogue {bis[4′-(isoquinolin-2-ium-4-yl)-2,2′:6′,2′′-terpyridine-1,1′′-diium] tris[tetrachloridozincate(II)] monohydrate; Granifo et al. (2017). Acta Cryst. C73, 1121–1130}, although rather different and much simpler in its structural features, mainly in the number and type of non-covalent interactions present, as well as in the supramolecular structure they define.

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18

Maroń, Anna, Agata Szlapa, Tomasz Klemens, et al. "Tuning the photophysical properties of 4′-substituted terpyridines – an experimental and theoretical study." Organic & Biomolecular Chemistry 14, no. 15 (2016): 3793–808. http://dx.doi.org/10.1039/c6ob00038j.

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19

Davidson, Ross J., Lucy E. Wilson, Andrew R. Duckworth, Dmitry S. Yufit, Andrew Beeby, and Paul J. Low. "Alkyne substituted mononuclear photocatalysts based on [RuCl(bpy)(tpy)]+." Dalton Transactions 44, no. 25 (2015): 11368–79. http://dx.doi.org/10.1039/c5dt01278c.

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The introduction of ‘wire-like’ arylene ethynylene substituent to the prototypical water oxidation catalyst precursor [RuCl(2,2′-bipyridine)(2,2′:6′,2′′-terpyridine)]PF<sub>6</sub>does not significantly alter the photostability of the compounds, nor the ability of the complexes to oxidise 4-methoxybenzyl alcohol to 4-methoxybenzaldehyde.

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20

Sen, Pinar, S. Zeki Yildiz, Göknur Yasa Atmaca, and Ali Erdogmus. "Five-nuclear phthalocyanine complex bearing terpyridine zinc complex: Synthesis, and photophysicochemical studies." Journal of Porphyrins and Phthalocyanines 22, no. 01n03 (2018): 181–88. http://dx.doi.org/10.1142/s1088424618500116.

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The context of this study is based on the synthesis of tetrakis{4-(2-([2,2[Formula: see text]:6[Formula: see text],2[Formula: see text]-terpyridine]Zn(II)-4[Formula: see text]-yl(methyl)amino)ethoxy)}phthalocyaninato zinc (II) (3) bearing four terpyridine-Zn(II) complexes that are directly linked through oxygen bridges to the macrocyclic core in order to create new supramolecular assemblies. The target phthalocyanine (3) was obtained by cyclotetramerization reaction of terpyridine-Zn (II) complex substituted phthalonitrile (2). All novel compounds synthesized in this study were fully characterized by general spectroscopic techniques such as FT-IR, UV-vis, and [Formula: see text]H-NMR, [Formula: see text]C-NMR, elemental analysis and mass spectroscopy. Spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen production and photodegradation under light irradiation) properties of newly synthesized phthalonitrile (2) and its phthalocyanine derivative (3) as five nuclear phthalocyanine were investigated in DMSO solutions.

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21

Panebianco, Roberta, Maurizio Viale, Valentina Giglio, and Graziella Vecchio. "Investigating the Anticancer Properties of Novel Functionalized Platinum(II)–Terpyridine Complexes." Inorganics 12, no. 6 (2024): 167. http://dx.doi.org/10.3390/inorganics12060167.

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Novel platinum(II) complexes of 4′-substituted terpyridine ligands were synthesized and characterized. Each complex had a different biomolecule (amine, glucose, biotin and hyaluronic acid) as a targeting motif, potentially improving therapeutic outcomes. We demonstrated that complexes can self-assemble in water into about 150 nm nanoparticles. Moreover, the complexes were assayed in vitro toward a panel of human cancer cell lines (ovarian adenocarcinoma A2780, lung cancer A549, breast adenocarcinoma MDA-MB-231, neuroblastoma SHSY5Y) to explore the impact of the pendant moiety on the terpyridine toxicity. The platinum complex of terpyridine amine derivative, [Pt(TpyNH2)Cl]Cl, showed the best antiproliferative effect, which was higher than cisplatin and [Pt(Tpy)Cl]Cl. Selective in vitro antiproliferative activity was achieved in A549 cancer cells with the Pt–HAtpy complex. These findings underline the potential of these novel platinum(II) complexes in cancer therapy and highlight the importance of tailored molecular design for achieving enhanced therapeutic effects.

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22

Okazawa, Atsushi, Takayuki Kakuchi, Keisuke Akahori, Kosuke Kawai, and Masashi Okubo. "Solubility-Enhanced Iron Complex Posolytes for Redox Flow Batteries." ECS Meeting Abstracts MA2024-02, no. 1 (2024): 16. https://doi.org/10.1149/ma2024-02116mtgabs.

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Redox flow batteries (RFBs) are promising stationary energy storage devices for renewables. Commercial RFBs possess potential disadvantages such as cost and resource constraint due to the use of vanadium. Therefore, organic compounds and metal coordination complexes have drawn much attention as redox active materials for RFB electrolytes. We focus on less expensive terpyridine iron complexes that have higher redox potential of approximately 1 V (vs. SHE) as an active material for both aqueous and non-aqueous RFB posolytes.[1] However, terpyridine iron complexes generally possess low solubility in nonaqueous and aqueous solvents. In this study, we improved the solubility of the complexes by multi-componentization based on asymmerizing molecular structures and using the diverse ion effect as shown in Figure 1, and then explored an application as active materials in posolytes. Symmetric terpyridine-iron complexes, [Fe(R-tpy)2](PF6)2 (R-tpy: substituted terpyridine ligand), were synthesized by simple mixing with R-tpy ligands and an iron source in high yields of 96-98%. Cyclic voltammogram of a butoxy-substituted complex, [Fe(BuOtpy)2]2+ (1BuO), shows redox potentials of 0.57 V (vs Fc/Fc+) in CH3CN. The Fe2+/Fe3+ redox couple shifts to a higher potential compared to 0.72 V (vs Fc/Fc+) for the parent complex, [Fe(tpy)2]2+ (1H), because of the electron-donating substituent on the ligand. The solubility of 1BuO·(PF6)2 in CH3CN was estimated as 0.13 M by a UV-Vis method using a calibration curve, which is comparable to that of 1H·(PF6)2 (0.16 M). Such a low solubility of 1BuO·(PF6)2 is due to a stronger lattice energy derived from a tight packing between the iron complex cations and PF6 −. The mixing of 1H and 1BuO produced a mixture containing a new asymmetric complex [Fe(BuOtpy)(tpy)]2+. The solubility of the mixture increased to 0.49 M, which enhances a theoretical volumetric capacity of posolytes three times than those of the single-component ones (Figure 2). Further solubility improvement was achieved using complexes substituted with poly(ethylene glycol)-type chains. Reference [1] A. Okazawa, T. Kakuchi, M. Okubo, APL Mater. 11, 110901 (2023). Figure 1

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23

Lar, Claudia, Gheorghe-Doru Roiban, Romina Crăsneanu, et al. "Synthesis and photophysical properties of some 6,6″-functionalized terpyridine derivatives." Open Chemistry 9, no. 2 (2011): 218–23. http://dx.doi.org/10.2478/s11532-010-0146-4.

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AbstractThe synthesis and photophysical properties of several 6,6″ symmetrically substituted 4′-aryl-2,2′:6′,2″-terpyridine derivatives are reported herein. The UV-Vis spectra in acetonitrile as well as in dichloromethane show two intense bands in the UV areas 252–262 nm and 275–290 nm while the fluorescence emission spectra are only slightly influenced by chemical derivatization.

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24

Hommes, Paul, and Hans-Ulrich Reissig. "Functionalization of Highly Substituted 2,2′:6′,2″-Terpyridine Derivatives." European Journal of Organic Chemistry 2016, no. 2 (2015): 338–42. http://dx.doi.org/10.1002/ejoc.201501299.

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25

Sutradhar, Sourav, Himadri Kushwaha, Vivekananda Samantaray, Parnashabari Sarkar, Dipankar Das, and Biswa Nath Ghosh. "Mercury selective hydrogelation of a pyridinyl substituted terpyridine ligand." Journal of Molecular Structure 1295 (January 2024): 136621. http://dx.doi.org/10.1016/j.molstruc.2023.136621.

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26

Pathan, Mosim, and Faiz Khan. "Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction." SynOpen 02, no. 02 (2018): 0150–60. http://dx.doi.org/10.1055/s-0036-1591960.

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Pyrido-oxazine derivatives have been synthesized by employing tandem SN2 and SNAr reaction between 2,4,6-tribromo-3-(2-bromoethoxy)pyridine or 2,4,6-tribromo-3-(3-bromopropoxy)pyridine and a variety of primary amines. Moderate to good regioselectivity in favor of cyclization at the 2-position is observed. Pyrido-oxazine products thus generated are converted into biarylated pyrido-oxazine and terpyridine ligands.

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27

Granifo, Juan, Sebastián Suárez, Fernando Boubeta, and Ricardo Baggio. "Crystallographic and computational study of a network composed of [ZnCl4]2− anions and triply protonated 4′-functionalized terpyridine cations." Acta Crystallographica Section C Structural Chemistry 73, no. 12 (2017): 1121–30. http://dx.doi.org/10.1107/s2053229617016308.

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We report herein the synthesis, crystallographic analysis and a study of the noncovalent interactions observed in the new 4′-substituted terpyridine-based derivative bis[4′-(isoquinolin-2-ium-4-yl)-2,2′:6′,2′′-terpyridine-1,1′′-diium] tris[tetrachloridozincate(II)] monohydrate, (C24H19N4)2[ZnCl4]3·H2O or (ITPH3)2[ZnCl4]3·H2O, where (ITPH3)3+ is the triply protonated cation derived from 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine (ITP) [Granifo et al. (2016). Acta Cryst. C72, 932–938]. The (ITPH3)3+ cation presents a number of interesting similarities and differences compared with its neutral ITP relative, mainly in the role fulfilled in the packing arrangement by the profuse set of D—H...A [D (donor) = C, N or O; A (acceptor) = O or Cl], π–π and anion...π noncovalent interactions present. We discuss these interactions in two different complementary ways, viz. using a point-to-point approach in the light of Bader's theory of Atoms In Molecules (AIM), analyzing the individual significance of each interaction, and in a more `global' analysis, making use of the Hirshfeld surfaces and the associated enrichment ratio (ER) approach, evaluating the surprisingly large co-operative effect of the superabundant weaker contacts.

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Masciello, Lucie, and Pierre G. Potvin. "One-pot synthesis of terpyridines and macrocyclization to C3-symmetric cyclosexipyridines." Canadian Journal of Chemistry 81, no. 3 (2003): 209–18. http://dx.doi.org/10.1139/v03-020.

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Four examples of 2,6-dicinnamoylpyridines were obtained in 6065% yields in condensations of commercially available 2,6-diacetylpyridine and benzaldehydes in 1:2 stoichiometry. At 2:1 ratios, four related 6,6''-diacetylated-4'-arylterpyridines were isolated in 7073% yields in one-pot condensations in the presence of NH3. 4,4'-Azo benzaldehyde, prepared from nitrobenzaldehyde in three steps and 40% overall yield was similarly converted to a novel azo-linked bis(terpyridine) in 50% yield in a reaction that assembles seven molecules in one step. The 6,6''-diacetylated-4'-arylterpyridines and the correspondingly substituted 2,6-dicinnamoylpyridines were condensed in 1:1 ratio together with NH3 to form 4,4'',4IV-triarylcyclosexipyridines in 2226% yields. These were obtained as mixed Na+ and K+ complexes and were insoluble amorphous solids, except for one example bearing 4-neopentoxyphenyl substituents. 1H NMR showed that the 4,4'',4IV-tri(4-neopentoxyphenyl)cyclosexipyridine complexes form aggregates in solution and at low concentrations show twofold symmetry arising from a loss of planarity.Key words: terpyridines, 4'-aryl-6,6''-diacetylterpyridines, azo-bisterpyridine, cyclosexipyridines, macrocyclization.

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29

Zhang, Guoqi, Jiawen Tan, Tonya Phoenix, David R. Manke, James A. Golen, and Arnold L. Rheingold. "Amalgamating 4′-substituted 4,2′:6′,4′′-terpyridine ligands with double-helical chains or ladder-like networks." RSC Advances 6, no. 11 (2016): 9270–77. http://dx.doi.org/10.1039/c5ra24044a.

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Hg<sup>II</sup>-mediated self-assembly of metal–organic coordination polymers based on 4,2′:6′,4′′-terpyridine derivatives is for the first time presented and the structural diversity dependent upon the use of 4′-substituents of ligand is revealed.

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30

Abdel-Shafi, Ayman A., Heba A. Amin, Iman A. Ghonium, Hesham S. Abdel-Samad, and Gehad Attia. "Photophysical Properties of some Ruthenium (II) Homoleptic substituted terpyridine complexes." Journal of Scientific Research in Science 41, no. 1 (2024): 159–77. https://doi.org/10.21608/jsrs.2024.259778.1123.

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31

Lin, Chih-Pei, Pas Florio, Eva M. Campi, et al. "Synthesis of substituted terpyridine ligands for use in protein purification." Tetrahedron 70, no. 45 (2014): 8520–31. http://dx.doi.org/10.1016/j.tet.2014.09.074.

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32

Gao, Y., Y. Song, Y. Li, Y. Wang, H. Liu, and D. Zhu. "Large optical limiting of [60]fullerene-substituted terpyridine palladium nanoparticles." Applied Physics B: Lasers and Optics 76, no. 7 (2003): 761–63. http://dx.doi.org/10.1007/s00340-003-1207-6.

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33

Mughal, Ehsan Ullah, Masoud Mirzaei, Amina Sadiq, et al. "Terpyridine-metal complexes: effects of different substituents on their physico-chemical properties and density functional theory studies." Royal Society Open Science 7, no. 11 (2020): 201208. http://dx.doi.org/10.1098/rsos.201208.

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A series of different substituted terpyridine (tpy)-based ligands have been synthesized by Kröhnke method. Their binding behaviour was evaluated by complexing them with Co(II), Fe(II) and Zn(II) ions, which resulted in interesting coordination compounds with formulae, [Zn(tpy) 2 ]PF 6 , [Co(tpy) 2 ](PF 6 ) 2 , [Fe(tpy) 2 ](PF 6 ) 2 and interesting spectroscopic properties. Their absorption and emission behaviours in dilute solutions were investigated in order to explain structure–property associations and demonstrate the impact of different aryl substituents on the terpyridine scaffold as well as the role of the metal on the complexes. Photo-luminescence analysis of the complexes in acetonitrile solution revealed a transition from hypsochromic to bathochromic shift. All the compounds displayed remarkable photo-luminescent properties and various maximum emission peaks owing to the different nature of the functional groups. Furthermore, the anti-microbial potential of ligands and complexes was evaluated with docking analyses carried out to investigate the binding affinity of terpyridine-based ligands along with corresponding proteins (shikimate dehydrogenase and penicillin-binding protein) binding sites. To obtain further insight into molecular orbital distributions and spectroscopic properties, density functional theory calculations were performed for representative complexes. The photophysical activity and interactions between chromophore structure and properties were both investigated experimentally as well as theoretically.

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34

Granifo, Juan, Beatriz Arévalo, Rubén Gaviño, Sebastián Suárez, and Ricardo Baggio. "Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine." Acta Crystallographica Section C Structural Chemistry 72, no. 12 (2016): 932–38. http://dx.doi.org/10.1107/s2053229616016533.

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4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π–π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24 (7)–7.90 (7)°, while the isq group is rotated significantly [by 46.57 (6)°] out of this planar scheme, associated with a short Htpy...Hisqcontact of 2.32 Å. There are no strong noncovalent interactions in the structure, the main ones being of the π–π and C—H...π types, giving rise to columnar arrays along [001], further linked by C—H...N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy...Hisqcontact of 2.32 Å to which AIM ascribed an attractive character.

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35

Zaguzin, A. S., G. Mahmoudi, F. I. Zubkov, et al. "Heteroligand Zn(II) Metal-Organic Frameworks Based on 4-Substituted 4,2':6',4"-Terpyridine Derivatives and Terephthalates." Координационная химия 49, no. 7 (2023): 406–11. http://dx.doi.org/10.31857/s0132344x23700251.

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Metal-organic frameworks based on Zn(II) and 4-substiuted 4,2':6',4"-terpyridine, terephthalate (Bdc), and 2-iodoterephthalate (2-I-Bdc) derivatives, {[Zn3(FurTerPy)2(Bdc)6]} (I), {[Zn(FurTerPy)(2-I-Bdc)}] (II), and {[Zn(PyrrTerPy)2(Bdc)} (III), were prepared and characterized by X-ray diffraction.

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36

Constable, Edwin C., Catherine E. Housecroft, Alessandro Prescimone, Srboljub Vujovic, and Jennifer A. Zampese. "Environmental control in the assembly of metallomacrocycles and one-dimensional polymers with 4,2′:6′:4′′-terpyridine linkers and zinc(ii) nodes." CrystEngComm 16, no. 37 (2014): 8691–99. http://dx.doi.org/10.1039/c4ce00783b.

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One-dimensional polymers and discrete [4 + 4] and [6 + 6] metallocycles assemble in reactions of 4′-aryl-substituted 4,2′:6′:4′′-terpyridines with ZnX<sub>2</sub> in the presence of potential arene guest molecules.

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37

Lee, Yung-Yuan, та Shiuh-Tzung Liu. "Preparation of Substituted Pyridines via a Coupling of β-Enamine Carbonyls with Rongalite-Application for Synthesis of Terpyridines". Reactions 3, № 3 (2022): 415–22. http://dx.doi.org/10.3390/reactions3030029.

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A Hantzsch-type strategy for the synthesis of 2,3,5,6-tetrasubstituted pyridines via an oxidative coupling of β-enamine carbonyl compounds with rongalite was developed. This method employs rongalite as a C1 unit for the assembly of a pyridine ring at C-4 position, offering a facile method for the preparation of substituted pyridine derivatives with a broad functional group tolerance. In particular, this method allows us to prepare terpyridine derivatives, which are important ligands or structural fragments for catalysts and 3D metal–organic frameworks.

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38

Fan, Congbin, Xiaomei Wang, and Jianfang Luo. "Blue organic light-emitting diodes based on terpyridine-substituted triphenylamine chromophores." Optical Materials 64 (February 2017): 489–95. http://dx.doi.org/10.1016/j.optmat.2017.01.018.

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39

Yin, Shouchun, Jing Zhang, Haike Feng, et al. "Zn2+-selective fluorescent turn-on chemosensor based on terpyridine-substituted siloles." Dyes and Pigments 95, no. 2 (2012): 174–79. http://dx.doi.org/10.1016/j.dyepig.2012.04.007.

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40

Loren, Jon C., and Jay S. Siegel. "Synthesis and Fluorescence Properties of Manisyl-Substituted Terpyridine, Bipyridine, and Phenanthroline." Angewandte Chemie 113, no. 4 (2001): 776–79. http://dx.doi.org/10.1002/1521-3757(20010216)113:4<776::aid-ange7760>3.0.co;2-p.

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41

Loren, Jon C., and Jay S. Siegel. "Synthesis and Fluorescence Properties of Manisyl-Substituted Terpyridine, Bipyridine, and Phenanthroline." Angewandte Chemie International Edition 40, no. 4 (2001): 754–57. http://dx.doi.org/10.1002/1521-3773(20010216)40:4<754::aid-anie7540>3.0.co;2-t.

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42

Cheng, Shu-Yuan, Qinguo Zhang, Quan Tang, Michelle C. Neary, and Shengping Zheng. "Diverse Cobalt(II) and Iron(II/III) Coordination Complexes/Polymers Based on 4′-Pyridyl: 2,2′;6′,2″-Terpyridine: Synthesis, Structures, Catalytic and Anticancer Activities." Chemistry 6, no. 5 (2024): 1099–110. http://dx.doi.org/10.3390/chemistry6050064.

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The success of platinum-based chemotherapeutic drugs for clinical cancer treatments has inspired tremendous research efforts on developing new metallic anticancer agents with improved cytotoxic activity and reduced side effects. 2,2′;6′,2″-Terpyridine and its 4′-substituted derivatives have showed great potential as ligand compartments for designing new anticancer drug candidates involving base metals. In this work, we synthesized a series of cobalt and iron coordination compounds based on 4′-pyridyl-2,2′;6′,2″-terpyridine, including homoleptic complexes, a dinuclear bridged complex and 1- and 2-dimensional coordination polymers/networks. The polymorphism of two homoleptic CoII and FeII complexes has been described along with the structural characterization of a CoII coordination polymer and dinuclear FeIII complex by X-ray crystallography. These compounds were tested preliminarily as precatalysts for the regioselective hydrosilylation of styrene. Their cytotoxic activities against two human breast cancer cell lines (MCF-7 and MDA-MB 468) and a normal breast epithelial cell line (MCF-10A) were investigated in order to observe the best-performing drug candidates.

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43

Patel, Kirti K., Edward A. Plummer, Muftah Darwish, Alison Rodger, and Michael J. Hannon. "Aryl substituted ruthenium bis-terpyridine complexes: intercalation and groove binding with DNA." Journal of Inorganic Biochemistry 91, no. 1 (2002): 220–29. http://dx.doi.org/10.1016/s0162-0134(01)00423-8.

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44

Bukhanko, Valerii, Isabelle Malfant, Zoia Voitenko, and Pascal Lacroix. "Isoindole and isomeric heterocyclic donating substituents in ruthenium(II)nitrosyl complexes with large first hyperpolarizabilities and potential two-photon absorption capabilities: a computational approach." French-Ukrainian Journal of Chemistry 5, no. 1 (2017): 8–23. http://dx.doi.org/10.17721/fujcv5i1p8-23.

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A set of 22 ruthenium nitrosyl complexes of general formula [RuII(L)Cl2(NO)]+ is investigated computationally by the density functional theory. L is a terpyridine ligand substituted by different R isomers of formula C12H8N, either indole, isoindole, or carbazole, proposed as alternative donors to the electron-rich fluorene substituent. The computed resulting nonlinear optical (NLO) properties are found to strongly depend on the isomer. While the ruthenium complexes exhibit modest efficiencies at the second-order (two-photon absorption) level, some of the R isomers lead to complexes of enhanced capabilities in first order (b) nonlinear optics. The synthetic feasibility of these ligands is discussed.

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45

Florio, Pas, Campbell J. Coghlan, Chih-Pei Lin, et al. "Isolation and Structure of a Hydrogen-bonded 2,2′:6′,2′′-Terpyridin-4′-one Acetic Acid Adduct." Australian Journal of Chemistry 67, no. 4 (2014): 651. http://dx.doi.org/10.1071/ch13571.

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Herein, we report the crystal structure of a key intermediate in the synthesis of 4′-substituted-terpyridines. Our findings confirm that the terpyridin-4′-one intermediate as generated from the condensation reaction of the corresponding triketone precursor with ammonium acetate is isolated as a hydrogen-bonded adduct with acetic acid, and not, as previously reported, as the acetate salt of a protonated pyridine nitrogen. This finding provides a rationale for the behaviour and structure of substituted terpyridin-4′-ones and pyridones in both the solid state and in solution.

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46

Maroń, Anna Maria, Oliviero Cannelli, Etienne Christophe Socie, Piotr Lodowski, and Barbara Machura. "Push-Pull Effect of Terpyridine Substituted by Triphenylamine Motive—Impact of Viscosity, Polarity and Protonation on Molecular Optical Properties." Molecules 27, no. 20 (2022): 7071. http://dx.doi.org/10.3390/molecules27207071.

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The introduction of an electron-donating triphenylamine motive into a 2,2′,6′,2′′-terpyridine (terpy) moiety, a cornerstone molecular unit in coordination chemistry, opens new ways for a rational design of photophysical properties of organic and inorganic compounds. A push-pull compound, 4′-(4-(di(4-tert-butylphenyl)amine)phenyl)-2,2′,6′,2′′-terpyridine (tBuTPAterpy), was thoroughly investigated with the use of steady-state and time-resolved spectroscopies and Density Functional Theory (DFT) calculations. Our results demonstrate that solvent parameters have an enormous influence on the optical properties of this molecule, acting as knobs for external control of its photophysics. The Intramolecular Charge Transfer (ICT) process introduces a remarkable solvent polarity effect on the emission spectra without affecting the lowest absorption band, as confirmed by DFT simulations, including solvation effects. The calculations ascribe the lowest absorption transitions to two singlet ICT excited states, S1 and S2, with S1 having several orders of magnitude higher oscillator strength than the “dark” S2 state. Temperature and viscosity investigations suggest the existence of two emitting excited states with different structural conformations. The phosphorescence emission band observed at 77 K is assigned to a localized 3terpy state. Finally, protonation studies show that tBuTPAterpy undergoes a reversible process, making it a promising probe of the pH level in the context of acidity determination.

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47

Fabre, B., U. Lehmann, and A. D. Schlüter. "Boronic ester-substituted terpyridine metal complex as a novel fluoride-sensitive redox receptor." Electrochimica Acta 46, no. 18 (2001): 2855–61. http://dx.doi.org/10.1016/s0013-4686(01)00492-3.

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48

Wang, Shih-Hao, Teng-Wei Wang, Hsieh-Chih Tsai, Po-Chih Yang, Chih-Feng Huang, and Rong-Ho Lee. "Synthesis of the diketopyrrolopyrrole/terpyridine substituted carbazole derivative based polythiophenes for photovoltaic cells." RSC Advances 10, no. 16 (2020): 9525–35. http://dx.doi.org/10.1039/c9ra09649c.

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49

Hubenthal, Frank, Nils Borg, Tobias Weidner, Ulrich Siemeling, and Frank Träger. "Gold nanoparticle growth on self-assembled monolayers of ferrocenyl-substituted terpyridine on graphite." Applied Physics A 94, no. 1 (2008): 11–17. http://dx.doi.org/10.1007/s00339-008-4888-1.

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50

Janjua, Muhammad Ramzan Saeed Ashraf, Wei Guan, Likai Yan, Zhong-Min Su, Abdul Karim, and Jamshed Akbar. "Quantum Chemical Design for Enhanced Second-Order NLO Response of Terpyridine-Substituted Hexamolybdates." European Journal of Inorganic Chemistry 2010, no. 22 (2010): 3466–72. http://dx.doi.org/10.1002/ejic.201000428.

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