Terpyridyl derivatives as bifunctional chelates: synthesis and crystal structures of 4′-[2-(1,3-dioxolan-2-yl)ethylsulfanyl]-2,2′∶6′,2″-terpyridine and chloro(4′-methylsulfanyl-2,2′∶6′,2″-terpyridine)gold(III) bis(trifluoromethanesulfonate) †

Sampath, UmaShanker; Putnam, William C.; Osiek, Todd A.; Touami, Sofia M.; Xie, Jin; Cohen, D. Walter; Cagnolini, Aldo; Droege, P.A.; Klug, David R.; Barnes, Charles L.; Modak, Anil; Bashkin, James K.; Jurisson, Silvia S.

doi:10.1039/a808557i

Cited by 41 publications

(39 citation statements)

References 71 publications

(66 reference statements)

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“…A new terpyridine functionalized with a halopropoxy, here a chloropropoxy, which could serve as an important intermediate for further terpyridine functionalization, was obtained by a functional group interconversion from the known hydroxyalkoxy-functionalized terpyridine 11, itself obtained through reaction of 4Ј-chloro-2,2Ј:6Ј,2ЈЈ-terpyridine (1) with an excess of propane-1,3-diol. [24] Reaction of 11 in refluxing SOCl 2 led to the (chloropropoxy)terpyridine 12, which, after recrystallization, was obtained as pure compound in 66% yield. An approach towards a metal-surfaceactive terpyridine was made by functionalizing the abovementioned aminoterpyridine 2 by reaction with racemic -thioctic acid utilizing the well-known DCC method in order to yield the dithiolane-functionalized terpyridine 14 in 35% yield (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

“…H 8.4, N 9.4; found C 78.7, H 8.4, N 9.5. 4Ј-(3-Chloropropoxy)-2,2Ј;6Ј,2ЈЈ-terpyridine (12): (Hydroxypropoxy)terpyridine 11 [24] (3.00 g, 9.76 mmol) was carefully added to 10 mL of SOCl 2 (resulting in heat development!) and refluxed for 5 h. The remaining SOCl 2 was removed in vacuo and the residue was neutralized with saturated NaHCO 3 solution.…”

Section: ј-Octyloxy-22ј:6ј2јј-terpyridine (8)mentioning

confidence: 99%

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New 4′‐Functionalized 2,2′:6′,2′′‐Terpyridines for Applications in Macromolecular Chemistry and Nanoscience

Andres

Lunkwitz²,

Pabst³

et al. 2003

Eur J Org Chem

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The well‐known reaction of 4′‐chloro‐2,2′:6′,2′′‐terpyridine with alkoxide nucleophiles leads to 4′‐functionalized 2,2′:6′,2′′‐terpyridines. This reaction allows the easy introduction of different functional groups onto the terpyridine at the 4′‐position, i.e. opposite to the metal binding site, in one reaction step. Among the functionalized 2,2′:6′,2′′‐terpyridines reported here are amines (including chiral examples), carboxylic acids, simple alkoxy‐chain terpyridines with different chain lengths, and a stilbene‐functionalized terpyridine. Moreover, the synthesis of two important already known substances was significantly improved. One example of a sequential functionalization of the (aminopentoxy)terpyridine with a dithiolane functionality is also reported. For two of the alkyl‐chain‐functionalized terpyridines, single‐crystal X‐ray crystallographic data were obtained. Finally, ordered monolayers of alkyl‐substituted terpyridines on HOPG were visualized using STM. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Resultsmentioning

confidence: 99%

Section: ј-Octyloxy-22ј:6ј2јј-terpyridine (8)mentioning

confidence: 99%

New 4′‐Functionalized 2,2′:6′,2′′‐Terpyridines for Applications in Macromolecular Chemistry and Nanoscience

Andres

Lunkwitz²,

Pabst³

et al. 2003

Eur J Org Chem

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“…For the synthesis of compounds 1, [10] 2, [11,12] 5, [13] and 7 [14] literature procedures were applied. NMR spectra were measured on a Bruker Mercury 400 and a Varian Gemini 300 NMR spectrometer.…”

Section: Materials and Characterizationmentioning

confidence: 99%

Metallo-Supramolecular Graft Copolymers: A Novel Approach Toward Polymer-Analogous Reactions

Schubert

Hofmeier

2002

Macromol. Rapid Commun.

103

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A copolymer of poly(methyl methacrylate) with terpyridine units in the side chains was synthesized utilizing free‐radical polymerization. The free terpyridine units were complexed with several different terpyridineruthenium mono‐complexes, yielding metallo‐supramolecular graft copolymers. The materials obtained were characterized by means of NMR and UV‐vis spectroscopy as well as GPC. Characterization by thermal analysis revealed distinct differences between these new materials and the initial copolymer.

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“…The nature of the DNA binding was found to be reversible. Liu et al [11] and Sampath et al [12] synthesized modified terpyridine gold(III) complexes at 4 0 position and the X-ray structures of [AuCl{4 0 -R(terpy)}](SO 3 CF 3 ) 2 (R = p-CH 3 OC 6 H 4 , CH 3 S) were reported. These structurally modified complexes exhibit interesting bifunctional substrates for DNA binding studies [13].…”

Section: Introductionmentioning

confidence: 97%

Crystal Structure Analysis of Two Chloro(2,2′:6′,2″-terpyridine)gold(III) Complexes

2012

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The X-ray crystal structure analysis of [AuCl-(terpy)](BF 4 ) 2 and [AuCl(terpy)](SO 3 CF 3 ) 2 show with the counter anions BF 4 -and SO 3 CF 3 -an expanded, more or less distorted octahedral coordination geometry. These secondary bonding interactions of the counter anions with the square planar complex cation [AuCl(terpy)] 2? are discussed and compared with those found in related gold(III) terpyridine complexes. In [AuCl(terpy)](SO 3 CF 3 ) 2 a very short non-bonding Au-O distance of 2.7641(4)Å of one of the triflate ions was found. The tetrafluoroborate complex is monoclinic with space group P2 1 / c and cell parameters a = 8.7587 (12)Å , b = 13.2623(19)Å , c = 15.537(2)Å , b = 90.362(2)°, V = 1804.7(4)Å 3 , Z = 4. The triflate complex is triclinic with space group P " 1 and cell parameters a = 7.4198(15)Å , b = 12.069(2)Å , c = 13.583(3)Å , a = 101.414(3)°, b = 101.922(3)°, c = 94.838(4)°, V = 1156.6(4)Å 3 , Z = 2.

show abstract

Terpyridyl derivatives as bifunctional chelates: synthesis and crystal structures of 4′-[2-(1,3-dioxolan-2-yl)ethylsulfanyl]-2,2′∶6′,2″-terpyridine and chloro(4′-methylsulfanyl-2,2′∶6′,2″-terpyridine)gold(III) bis(trifluoromethanesulfonate) †

Cited by 41 publications

References 71 publications

New 4′‐Functionalized 2,2′:6′,2′′‐Terpyridines for Applications in Macromolecular Chemistry and Nanoscience

New 4′‐Functionalized 2,2′:6′,2′′‐Terpyridines for Applications in Macromolecular Chemistry and Nanoscience

Metallo-Supramolecular Graft Copolymers: A Novel Approach Toward Polymer-Analogous Reactions

Crystal Structure Analysis of Two Chloro(2,2′:6′,2″-terpyridine)gold(III) Complexes

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