The interplay of coordinative, hydrogen bonding and π–π stacking interactions in sustaining supramolecular solid-state architectures.

Roesky, Herbert W.; Andruh, Marius

doi:10.1016/s0010-8545(02)00218-7

Cited by 718 publications

(282 citation statements)

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“…The stacking interactions as well as hydrogen bonds are essential for the structural stability and function of DNA and RNA and for self-assembly or recognition processes when extended structures are formed from building blocks with aromatic moieties. [31][32][33][34] Our previous studies demonstrate that 1,10-phenanthroline is one of the most favorable bidentate ligands to display p-p stacking supramolecular interactions in the crystal due to its large aromatic system. 35 As dealt with before, 36,37 two stacking phenanthroline molecules are divided into four pyridine (A, A′, C and C′) and two arene (B and B′) segments in order to facilitate the description of this extended p system.…”

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confidence: 99%

Crystal structure, supramolecular self-assembly and interaction with DNA of a mixed ligand manganese(II) complex

Sun¹,

Dong²,

Wang³

et al. 2011

J. Braz. Chem. Soc.

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Um complexo misto de manganês(II), [Mn(sal)(phen) 2 ]ClO 4 (1) (sal = salicilaldeído, phen = 1,10-fenantrolina), foi sintetizado e caracterizado por análise elementar e difração de raio-X de monocristais. A análise dos difratogramas revelou que o complexo 1 cristaliza no grupo espacial monoclínico P2 1 /n. A unidade assimétrica do complexo é composta do cátion complexo [Mn(sal)(phen) 2 ] + e do ânion perclorato não coordenado. O manganês(II) está num ambiente de coordenação MnN 4 O 2 de geometria octaédrica bem distorcida. Quatro tipos de empilhamento p-p envolvendo ligantes fenantrolina e salicilaldeído estão envolvidos na auto-montagem supramolecular. Estas interações de empilhamento aromático cooperam com ligações de hidrogênio para a montagem de uma fascinante arquitetura supramolecular 3D com o complexo. Estudos de espectroscopia de absorção eletrônica e de titulação monitorando-se a fluorescência de 1 com DNA de timo de bezerro sugerem a ligação do complexo por intercalação com uma constante de formação igual a 7,97×10 3 L mol −1 e uma constante de supressão de Stern-Volmer de 1,34×10 4 L mol −1 .A mixed ligand manganese(II) complex, [Mn(sal)(phen) 2 ]ClO 4 (1) (sal = salicylaldehyde, phen = 1,10-phenanthroline), has been synthesized and characterized by elemental analysis and single crystal X-ray diffractometry. The structural analysis revealed that complex 1 crystallizes in the monoclinic space group P2 1 /n. The asymmetric unit of the complex is comprised of [Mn(sal)(phen) 2 ] + complex cation and uncoordinated perchlorate anion. The manganese(II) is located in a seriously distorted octahedral MnN 4 O 2 coordination environment. Four types of p-p stacking modes involving phenanthroline and salicylaldehyde ligands are involved in the supramolecular self-assembly. These aromatic stacking interactions cooperate with hydrogen bonding to assemble the complex into a fascinating 3D supramolecular architecture. Electronic absorption spectroscopy and fluorescence titration studies of the interaction between complex 1 and calf thymus DNA suggest an intercalative binding mode with a constant of 7.97×10 3 L mol −1 and a Stern-Volmer quenching constant of 1.34×10 4 L mol −1 .Keywords: manganese(II) complex, crystal structure, supramolecular self-assembly, DNA interaction, spectrum IntroductionMuch attention has been given to rational design, synthesis and characterization of new transition metal complexes in the past decades because some of them can interact with DNA acting as probes for nucleic acid structure manipulation or exhibiting nuclease property. [1][2][3][4][5] Metal complex can bind to DNA in non-covalent way such as by electrostatic interaction, minor or major groove-bound fashion and intercalation. 6,7 Considerable efforts are yet necessary to develop novel metal complexes binding to DNA through an intercalative association because of their unique properties and applications. [8][9][10][11][12][13] A metallointercalator binds DNA through the insertion of a planar polycyclic aromatic 23 also present int...

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confidence: 99%

Crystal structure, supramolecular self-assembly and interaction with DNA of a mixed ligand manganese(II) complex

Sun¹,

Dong²,

Wang³

et al. 2011

J. Braz. Chem. Soc.

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“…Central naphthalene ring torsion angles C: (6)- (5)- (10)- (1) (1) C: (4)- (5)- (10)- (9) 179.55 (1) 178.69 (1) In comparison, the 31 P{ 1 H} NMR spectra of complexes 2 and 6 display the expected pattern for the AA` nuclei of an AA`X spin system. [26] In addition to the established single resonances accompanied by platinum satellites [2 δ = 20.19 31 P A`) coupling constants are notoriously small for AA`X spin systems [27] and were not observed in the 31 P{ 1 H} NMR spectra of complexes 2, 4 and 6. The partial solubility of the complexes also made obtaining 77 Se NMR spectra with reasonable signal-to-noise ratios for these complexes problematic.…”

Section: Resultsmentioning

confidence: 99%

“…Reaction scheme for the preparation of bisphosphine complexes [Pt(5,6-AcenapE2)(PR3)2] 1-6 bearing 5,6-dihydroacenaphtho [5,6-cd]-1,2-dichalcogenoles L1 and L2. 31 P{ 1 H} NMR spectroscopic data for the series of bisphoshine complexes is displayed in Table 1. The spectra of complexes 1, 3 and 5, bearing the sulfur ligand L1, display anticipated single resonances with platinum satellites, moving to lower chemical shifts as the alkyl group on phosphorus is varied from R 3 = Ph 3 to R 3 =PhMe 2 [1 δ = 23.52 ppm, 1 J( 31 P, 195 Pt) = 2980 Hz; 3 δ = 4.51 ppm, 1 J( 31 P, 195 Pt) = 2926 Hz; 5 δ = -13.14 ppm 1 J( 31 P, 195 Pt) = 2861 Hz].…”

Section: Resultsmentioning

confidence: 99%

“…In complexes 1 and 2, two neighbouring phenyl rings attached to independent P atoms adopt a parallel alignment similar to the face-to-face offset arrangement (Figure 7), [31] with non-bonded distances between interacting centroids (cg (25)(26)(27)(28)(29)(30)···cg (31)(32)(33)(34)(35)(36): 1 3.765(1)Å; 2 3.764(1)Å) within the range for typical π···π stacking (3.3-3.8 Å). [31] Similarly, complexes 5 and 6 exhibit weak CH···π type non-conventional hydrogen bond interactions [32] between neighbouring methyl and phenyl moieties of adjacent phosphorus groups (5 C(14)-H(14C)···cg (23-28) Unsurprisingly, cleavage of the short E-E covalent bond and subsequent coordination to platinum in complexes 1, 2, 5 and 6 causes steric strain to accumulate between the bulky chalcogen atoms. Repulsive interactions between the two perifunctionalities, resulting from sub-van der Waals contacts, leads to deformation of the carbon framework via in-plane and out-ofplane distortions and buckling of the aromatic ring system (angular strain), ultimately disrupting the relaxed geometry previously achieved by the free ligands.…”

Section: X-ray Investigationsmentioning

confidence: 88%

“…Interestingly, whilst neighbouring phenyl rings of complex N2 overlap, the distance between the two interacting centroids (4.167(1) Å [4.166(1) Å]) is outside the range for standard π···π stacking to occur (3.3-3.8 Å). [12,31] …”

Section: X-ray Investigationsmentioning

confidence: 99%

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Platinum Complexes of 5,6‐Dihydroacenaphtho[5,6‐cd]‐1,2‐dichalcogenoles

et al. 2012

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Six platinum bisphosphine complexes, bearing dichalcogen acenaphthene ligands, have been prepared by metathesis from cis-[PtCl 2 (PR 3 ) 2 ] (R 3 = Ph 3 , Ph 2 Me, PhMe 2 ) and the dilithium salts of the parent 5,6-dihydroacenaphtho[5,6-cd]-1,2-dichalcogenoles [AcenapE 2 ] (L1 E = S, L2 E = Se). For their synthesis, the appropriate disulfide or diselenide species was treated with super hydride [LiBEt 3 H] affording the dilithium salt by in situ reduction of the AcenapE 2 E-E bond. Further reaction, via metathetical addition to the cis-platinum precursor afforded the respective platinum(II) complex [Pt(5,6-AcenapE 2 )(PR 3 ) 2 ] (R 3 = Ph 3 : E = S 1, Se 2; R 3 = Ph 2 Me: E = S 3, Se 4; R 3 = PhMe 2 : E = S 5, Se 6).All six complexes have been fully characterised, principally by multinuclear magnetic resonance spectroscopy, IR and MS. Selenium complexes 4 and 6 provide examples of AA`X spin systems, as displayed by their 31 P{ 1 H} NMR spectra. X-ray structures were determined for L1, L2, 1, 2, 5 and 6 and analysed, where appropriate, by platinum metal geometry, periatom displacement, splay angle magnitude, acenaphthene ring torsion angles and E···E interactions. Platinum was found to adopt a distorted square-planar geometry in all four complexes, with the nature of the AcenapE 2 ligand playing little part in the conformation of the substituents bound to the trivalent phosphorus atoms.____________ [a] EASTChem, School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK. Fax: (+44)1334 463384 E-mail: jdw3@st-and.ac.uk Supporting information for this article is available on the WWW under http://www.eurjic.org/ or from the author. IntroductionThe coordination chemistry of peri-substituted naphthalenes and structurally related systems has been developed over the last 15 years. [1] Geometric constraints unique to these frameworks are imposed by a double substitution at the peri-positions (positions 1 and 8 of the naphthalene ring, 5 and 6 of acenaphthene), [2,3] placing large heteroatoms or groups in close proximity, usually within van der Waals radii.[4] A number of investigators have utilised this characteristic of the naphthalene scaffold to study bonding interactions in main group systems, where molecular geometry is determined by a competition between attractive (covalent and weak) forces and repulsive interactions (steric strain). [5,6] The distinguishing feature of peri-substitution is the ability to achieve a relaxed geometry via formation of a direct bond between the two peri-atoms. [7] Furthermore, proximity effects associated with peri-substitution favours complexation to a bridging metal species, providing the correct spacial arrangement for bidentate coordination.Transition metal complexes incorporating 1,8-disubstituted naphthalene ligands have been well documented, [1] with the majority of examples reported bearing either bis(phosphine) or bis(thiolate) functionalities. Complexes assembled from ligands with Group 16 donor atoms invariably contain the naphthalene-1,8-dichalcogenol...

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Silver(I) Coordination Polymers

Chen

Zhang

et al. 2009

Design and Construction of Coordination Polymers

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The interplay of coordinative, hydrogen bonding and π–π stacking interactions in sustaining supramolecular solid-state architectures.

Cited by 718 publications

References 103 publications

Crystal structure, supramolecular self-assembly and interaction with DNA of a mixed ligand manganese(II) complex

Crystal structure, supramolecular self-assembly and interaction with DNA of a mixed ligand manganese(II) complex

Platinum Complexes of 5,6‐Dihydroacenaphtho[5,6‐cd]‐1,2‐dichalcogenoles

Silver(I) Coordination Polymers

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