?-? Interactions in Self-Assembly

Claessens, Christian G.; Stoddart, J. Fraser

doi:10.1002/(sici)1099-1395(199705)10:5<254::aid-poc875>3.0.co;2-3

Cited by 396 publications

(213 citation statements)

References 73 publications

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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.…”

Section: Non-covalent Interactions and Supramolecular Selfassemblymentioning

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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Section: Non-covalent Interactions and Supramolecular Selfassemblymentioning

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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“…8,9 Certain drugs rely on π-π interactions for intercalation into DNA. 10,11 While these interactions have been studied extensively, [12][13][14][15][16][17][18][19][20][21][22][23][24] their relative weakness and shallow potential energy surface makes them challenging to describe by either experiment or theory. [25][26][27][28][29] The binding energy of the gas-phase benzene dimer, for example, is 2-3 kcal/mol, and the dimer is stable only at low temperatures.…”

Section: Introductionmentioning

confidence: 99%

Modeling π–π Interactions with the Effective Fragment Potential Method: The Benzene Dimer and Substituents

2008

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This study compares the results of the general effective fragment potential (EFP2) method to the results of a previous combined coupled cluster with single, double, and perturbative triple excitations [CCSD(T)] and symmetry-adapted perturbation theory (SAPT) study [Sinnokrot and Sherrill, J. Am. Chem. Soc., 2004, 126, 7690] on substituent effects in π-π interactions. EFP2 is found to accurately model the binding energies of the benzene-benzene, benzene-phenol, benzene-toluene, benzene-fluorobenzene, and benzene-benzonitrile dimers, as compared with high-level methods [Sinnokrot and Sherrill, J. Am. Chem. Soc., 2004, 126, 7690], but at a fraction of the computational cost of CCSD(T). In addition, an EFP-based Monte Carlo/simulated annealing study was undertaken to examine the potential energy surface of the substituted dimers.

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“…Aromatic-aromatic or p-p stacking interactions are well known as effective noncovalent intermolecular forces, which are normally employed for H-type or J-type stacking of aromatic groups with ring centroid-centroid distances of B3.3-3.8 Å [25][26][27] . In particular, they can facilitate self-assembly or molecular recognition processes while involving extended structures that are constructed from building blocks with aromatic moieties to matching MFI nanosheet 28,29 . The presence of at least two benzene rings is known to be necessary for the formation of stable bilayer assemblies of amphiphiles 30 .…”

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confidence: 99%

π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets

et al. 2014

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One of the challenges in material science has been to prepare macro-or mesoporous zeolite. Although examples of their synthesis exist, there is a need for a facile yet versatile approach to such hierarchical structures. Here we report a concept for designing a single quaternary ammonium head amphiphilic template with strong ordered self-assembling ability through p-p stacking in hydrophobic side, which stabilizes the mesostructure to form singlecrystalline mesostructured zeolite nanosheets. The concept is demonstrated for the formation of a new type of MFI (zeolite framework code by International Zeolite Association) nanosheets joined with a 90°rotational boundary, which results in a mesoporous zeolite with highly specific surface area even after calcination. Low binding energies for this selfassembling system are supported by a theoretical analysis. A geometrical matching between the arrangement of aromatic groups and the zeolitic framework is speculated for the formation of single-crystalline MFI nanosheets.

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?-? Interactions in Self-Assembly

Cited by 396 publications

References 73 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

Modeling π–π Interactions with the Effective Fragment Potential Method: The Benzene Dimer and Substituents

π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets

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